TY 2022 Form 990

- TIN:

Form990

Department of the TreasuryInternal Revenue Service

Return of Organization Exempt From Income Tax

Under section 501(c), 527, or 4947(a)(1) of the Internal Revenue Code (except private foundations)

Do not enter social security numbers on this form as it may be made public.

Go to www.irs.gov/Form990 for instructions and the latest information.

OMB No. 1545-0047

2021

Open to Public Inspection

A For the 2021 calendar year, or tax year beginning 01-01-2022 , and ending 06-30-2022

BCheck if applicable: Address change Name change Initial return Final return/terminated Amended return Application pending

CName of organization
CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Doing business as

Number and street (or P.O. box if mail is not delivered to street address)
8722 LOCH RAVEN BOULEVARD

Room/suite

City or town, state or province, country, and ZIP or foreign postal code
TOWSON, MD212862235

D Employer identification number

46-1056754

E Telephone number

G Gross receipts $ 705,509,490

F Name and address of principal officer:
THOMAS PHELAN
8722 LOCH RAVEN BOULEVARD
TOWSON,MD212862235

Tax-exempt status: 501(c)(3) 501(c) ( 27 ) LeftBullet

(insert no.) 4947(a)(1) or 527

Website:

WWW.CEIWC.COM

H(a)

Is this a group return for
subordinates? Yes No

H(b)

Are all subordinates
included?

Yes No

If "No," attach a list. See instructions.

H(c)

Group exemption number MediumBullet

K Form of organization: Corporation Trust Association Other MediumBullet

L Year of formation: 2012

M State of legal domicile: MD

Part I

Summary

1	Briefly describe the organization’s mission or most significant activities: CHESAPEAKE EMPLOYERS' INSURANCE COMPANY WAS ESTABLISHED BY STATUTE TO BE THE WORKERS' COMPENSATION INSURER OF LAST RESORT AS WELL AS A COMPETITIVE INSURER IN THE STATE OF MARYLAND.
2	Check this box
3	Number of voting members of the governing body (Part VI, line 1a) ........	3	9
4	Number of independent voting members of the governing body (Part VI, line 1b) .....	4	0
5	Total number of individuals employed in calendar year 2021 (Part V, line 2a) ......	5	0
6	Total number of volunteers (estimate if necessary) .............	6	0
7a	Total unrelated business revenue from Part VIII, column (C), line 12 ........	7a	0
b	Net unrelated business taxable income from Form 990-T, Part I, line 11 .........	7b	0

		Prior Year	Current Year
8	Contributions and grants (Part VIII, line 1h) .........	0	0
9	Program service revenue (Part VIII, line 2g) .........	169,321,067	91,457,426
10	Investment income (Part VIII, column (A), lines 3, 4, and 7d ) ....	167,646,106	42,411,194
11	Other revenue (Part VIII, column (A), lines 5, 6d, 8c, 9c, 10c, and 11e)	103,572	1,005,672
12	Total revenue—add lines 8 through 11 (must equal Part VIII, column (A), line 12)	337,070,745	134,874,292
13	Grants and similar amounts paid (Part IX, column (A), lines 1–3 )...	302,325	126,326
14	Benefits paid to or for members (Part IX, column (A), line 4).....	0	0
15	Salaries, other compensation, employee benefits (Part IX, column (A), lines 5–10)	40,939,190	20,047,890
16a	Professional fundraising fees (Part IX, column (A), line 11e) .....	0	0
b	Total fundraising expenses (Part IX, column (D), line 25) 0
17	Other expenses (Part IX, column (A), lines 11a–11d, 11f–24e)....	168,464,787	81,057,645
18	Total expenses. Add lines 13–17 (must equal Part IX, column (A), line 25)	209,706,302	101,231,861
19	Revenue less expenses. Subtract line 18 from line 12.......	127,364,443	33,642,431
		Beginning of Current Year	End of Year
20	Total assets (Part X, line 16).............	2,512,331,700	0
21	Total liabilities (Part X, line 26).............	1,374,799,656	0
22	Net assets or fund balances. Subtract line 21 from line 20.....	1,137,532,044	0

Part II

Signature Block

Under penalties of perjury, I declare that I have examined this return, including accompanying schedules and statements, and to the best of my knowledge and belief, it is true, correct, and complete. Declaration of preparer (other than officer) is based on all information of which preparer has any knowledge.

Sign Here

	Signature of officer	Date

	Type or print name and title

Paid Preparer Use Only

Print/Type preparer's name

Preparer's signature

Date

Check if
self-employed

PTIN

Firm's name MediumBullet

Firm's EIN MediumBullet

Firm's address MediumBullet

Phone no.

May the IRS discuss this return with the preparer shown above? (see instructions) ..........YesNo

For Paperwork Reduction Act Notice, see the separate instructions.

Cat. No. 11282Y Form 990 (2021)

Form 990 (2021)

Page 2

Part III

Statement of Program Service Accomplishments

Check if Schedule O contains a response or note to any line in this Part III..............

Briefly describe the organization’s mission: CHESAPEAKE EMPLOYERS' INSURANCE COMPANY WAS ESTABLISHED BY STATUTE TO BE THE WORKERS' COMPENSATION INSURER OF LAST RESORT AS WELL AS A COMPETITIVE INSURER IN THE STATE OF MARYLAND.

Did the organization undertake any significant program services during the year which were not listed on
the prior Form 990 or 990-EZ? ..................... Yes No

If "Yes," describe these new services on Schedule O.

Did the organization cease conducting, or make significant changes in how it conducts, any program
services? ........................... Yes No

If "Yes," describe these changes on Schedule O.

Describe the organization’s program service accomplishments for each of its three largest program services, as measured by expenses. Section 501(c)(3) and 501(c)(4) organizations are required to report the amount of grants and allocations to others, the total expenses, and revenue, if any, for each program service reported.


4a	(Code: ) (Expenses $ including grants of $ ) (Revenue $ )
	CHESAPEAKE EMPLOYERS' INSURANCE COMPANY HAD OVER 20,500 IN-FORCE POLICIES AND WAS MANAGING MORE THAN 2,910 OPEN CLAIMS AT JUNE 30, 2022.

4b	(Code: ) (Expenses $ including grants of $ ) (Revenue $ )












4c	(Code: ) (Expenses $ including grants of $ ) (Revenue $ )












4d	Other program services (Describe in Schedule O.)
	(Expenses $ including grants of $ ) (Revenue $ )
4e	Total program service expenses

Form 990 (2021)

Page 3

Part IV

Checklist of Required Schedules

Yes

Is the organization described in section 501(c)(3) or 4947(a)(1) (other than a private foundation)? If "Yes," complete Schedule A.....................

Is the organization required to complete Schedule B, Schedule of Contributors? See instructions. ...

Did the organization engage in direct or indirect political campaign activities on behalf of or in opposition to candidates for public office? If "Yes," complete Schedule C, Part I.............

Section 501(c)(3) organizations. Did the organization engage in lobbying activities, or have a section 501(h) election in effect during the tax year? If "Yes," complete Schedule C, Part II.........

Is the organization a section 501(c)(4), 501(c)(5), or 501(c)(6) organization that receives membership dues, assessments, or similar amounts as defined in Rev. Proc. 98-19? If "Yes," complete Schedule C, Part III..

Did the organization maintain any donor advised funds or any similar funds or accounts for which donors have the right to provide advice on the distribution or investment of amounts in such funds or accounts? If "Yes," complete Schedule D, Part I Click to see attachment

List of Attached Documents:

// Content

.........................

Did the organization receive or hold a conservation easement, including easements to preserve open space,
the environment, historic land areas, or historic structures? If "Yes," complete Schedule D, Part II Click to see attachment

List of Attached Documents:

// Content

....

Did the organization maintain collections of works of art, historical treasures, or other similar assets? If "Yes,"
complete Schedule D, Part III Click to see attachment

List of Attached Documents:

// Content

..............

Did the organization report an amount in Part X, line 21 for escrow or custodial account liability; serve as a custodian for amounts not listed in Part X; or provide credit counseling, debt management, credit repair, or debt negotiation services? If "Yes," complete Schedule D, Part IV Click to see attachment

List of Attached Documents:

// Content

..............

Did the organization, directly or through a related organization, hold assets in temporarily restricted endowments, permanent endowments, or quasi endowments? If "Yes," complete Schedule D, Part V......

If the organization’s answer to any of the following questions is "Yes," then complete Schedule D, Parts VI, VII, VIII, IX, or X, as applicable.

Did the organization report an amount for land, buildings, and equipment in Part X, line 10? If "Yes," complete
Schedule D, Part VI. Click to see attachment

List of Attached Documents:

// Content

...................

11a

Did the organization report an amount for investments—other securities in Part X, line 12 that is 5% or more of its total assets reported in Part X, line 16? If "Yes," complete Schedule D, Part VII Click to see attachment

List of Attached Documents:

// Content

.......

11b

Did the organization report an amount for investments—program related in Part X, line 13 that is 5% or more of its total assets reported in Part X, line 16? If "Yes," complete Schedule D, Part VIII Click to see attachment

List of Attached Documents:

// Content

.......

11c

Did the organization report an amount for other assets in Part X, line 15 that is 5% or more of its total assets reported in Part X, line 16? If "Yes," complete Schedule D, Part IX Click to see attachment

List of Attached Documents:

// Content

............

11d

Did the organization report an amount for other liabilities in Part X, line 25? If "Yes," complete Schedule D, Part X Click to see attachment

List of Attached Documents:

// Content

11e

Did the organization’s separate or consolidated financial statements for the tax year include a footnote that addresses the organization’s liability for uncertain tax positions under FIN 48 (ASC 740)? If "Yes," complete Schedule D, Part X Click to see attachment

List of Attached Documents:

// Content

11f

Yes

12a

Did the organization obtain separate, independent audited financial statements for the tax year? If "Yes," complete
Schedule D, Parts XI and XII Click to see attachment

List of Attached Documents:

// Content

......................

12a

Was the organization included in consolidated, independent audited financial statements for the tax year? If "Yes," and if the organization answered "No" to line 12a, then completing Schedule D, Parts XI and XII is optional Click to see attachment

List of Attached Documents:

// Content

12b

Yes

Is the organization a school described in section 170(b)(1)(A)(ii)? If "Yes," complete Schedule E

14a

Did the organization maintain an office, employees, or agents outside of the United States? .....

14a

Did the organization have aggregate revenues or expenses of more than $10,000 from grantmaking, fundraising, business, investment, and program service activities outside the United States, or aggregate foreign investments valued at $100,000 or more? If "Yes," complete Schedule F, Parts I and IV.........

14b

Did the organization report on Part IX, column (A), line 3, more than $5,000 of grants or other assistance to or for any foreign organization? If “Yes,” complete Schedule F, Parts II and IV.....

Did the organization report on Part IX, column (A), line 3, more than $5,000 of aggregate grants or other assistance to or for foreign individuals? If “Yes,” complete Schedule F, Parts III and IV...

Did the organization report a total of more than $15,000 of expenses for professional fundraising services on Part IX, column (A), lines 6 and 11e? If "Yes," complete Schedule G, Part I. See instructions. ....

Did the organization report more than $15,000 total of fundraising event gross income and contributions on Part VIII, lines 1c and 8a? If "Yes," complete Schedule G, Part II............

Did the organization report more than $15,000 of gross income from gaming activities on Part VIII, line 9a? If "Yes," complete Schedule G, Part III...................

20a

Did the organization operate one or more hospital facilities? If "Yes," complete Schedule H....

20a

If "Yes" to line 20a, did the organization attach a copy of its audited financial statements to this return?

20b

Did the organization report more than $5,000 of grants or other assistance to any domestic organization or domestic government on Part IX, column (A), line 1? If “Yes,” complete Schedule I, Parts I and II..... Click to see attachment

List of Attached Documents:

// Content

Yes

Form 990 (2021)

Page 4

Part IV

Checklist of Required Schedules (continued)

Yes

Did the organization report more than $5,000 of grants or other assistance to or for domestic individuals on Part IX, column (A), line 2? If “Yes,” complete Schedule I, Parts I and III........ Click to see attachment

List of Attached Documents:

// Content

Did the organization answer "Yes" to Part VII, Section A, line 3, 4, or 5, about compensation of the organization’s current and former officers, directors, trustees, key employees, and highest compensated employees? If "Yes," complete Schedule J....................... Click to see attachment

List of Attached Documents:

// Content

Yes

24a

Did the organization have a tax-exempt bond issue with an outstanding principal amount of more than $100,000 as of the last day of the year, that was issued after December 31, 2002? If “Yes,” answer lines 24b through 24d and complete Schedule K. If “No,” go to line 25a...............

24a

Did the organization invest any proceeds of tax-exempt bonds beyond a temporary period exception?...

24b

Did the organization maintain an escrow account other than a refunding escrow at any time during the year
to defease any tax-exempt bonds? ...............

24c

Did the organization act as an "on behalf of" issuer for bonds outstanding at any time during the year?...

24d

25a

Section 501(c)(3), 501(c)(4), and 501(c)(29) organizations. Did the organization engage in an excess benefit transaction with a disqualified person during the year? If "Yes," complete Schedule L, Part I ....

25a

Is the organization aware that it engaged in an excess benefit transaction with a disqualified person in a prior year, and that the transaction has not been reported on any of the organization’s prior Forms 990 or 990-EZ? If "Yes," complete Schedule L, Part I.......................

25b

Did the organization report any amount on Part X, line 5 or 22 for receivables from or payables to any current or former officer, director, trustee, key employee, creator or founder, substantial contributor, or 35% controlled entity or family member of any of these persons? If "Yes," complete Schedule L, Part II...........

Did the organization provide a grant or other assistance to any current or former officer, director, trustee, key employee, creator or founder, substantial contributor, or employee thereof, a grant selection committee member, or to a 35% controlled entity (including an employee thereof) or family member of any of these persons?

If "Yes," complete

Schedule L, Part III.........................

Was the organization a party to a business transaction with one of the following parties (see the Schedule L, Part IV instructions for applicable filing thresholds, conditions, and exceptions):

A current or former officer, director, trustee, key employee, creator or founder, or substantial contributor? If "Yes," complete Schedule L, Part IV......................

28a

A family member of any individual described in line 28a? If "Yes," complete Schedule L, Part IV.....

28b

A 35% controlled entity of one or more individuals and/or organizations described in line 28a or 28b? If "Yes," complete Schedule L, Part IV.....................

28c

Did the organization receive more than $25,000 in non-cash contributions? If "Yes," complete Schedule M..

Did the organization receive contributions of art, historical treasures, or other similar assets, or qualified conservation contributions? If "Yes," complete Schedule M .................

Did the organization liquidate, terminate, or dissolve and cease operations? If "Yes," complete Schedule N, Part I Click to see attachment

List of Attached Documents:

// Content

Yes

Did the organization sell, exchange, dispose of, or transfer more than 25% of its net assets? If "Yes," complete Schedule N, Part II........................ Click to see attachment

List of Attached Documents:

// Content

Did the organization own 100% of an entity disregarded as separate from the organization under Regulations sections 301.7701-2 and 301.7701-3? If "Yes," complete Schedule R, Part I............ Click to see attachment

List of Attached Documents:

// Content

Yes

Was the organization related to any tax-exempt or taxable entity? If "Yes," complete Schedule R, Part II, III, or IV, and Part V, line 1......................... Click to see attachment

List of Attached Documents:

// Content

Yes

35a

Did the organization have a controlled entity within the meaning of section 512(b)(13)?

35a

Yes

If ‘Yes’ to line 35a, did the organization receive any payment from or engage in any transaction with a controlled entity within the meaning of section 512(b)(13)? If "Yes," complete Schedule R, Part V, line 2 ... Click to see attachment

List of Attached Documents:

// Content

35b

Section 501(c)(3) organizations. Did the organization make any transfers to an exempt non-charitable related organization? If "Yes," complete Schedule R, Part V, line 2.............

Did the organization conduct more than 5% of its activities through an entity that is not a related organization and that is treated as a partnership for federal income tax purposes? If "Yes," complete Schedule R, Part VI Click to see attachment

List of Attached Documents:

// Content

Did the organization complete Schedule O and provide explanations on Schedule O for Part VI, lines 11b and 19? Note. All Form 990 filers are required to complete Schedule O. ............

Yes

Part V

Statements Regarding Other IRS Filings and Tax Compliance
Check if Schedule O contains a response or note to any line in this Part V...........

Yes

Enter the number reported in box 3 of Form 1096. Enter -0- if not applicable ..

Enter the number of Forms W-2G included on line 1a. Enter -0- if not applicable .

Did the organization comply with backup withholding rules for reportable payments to vendors and reportable gaming (gambling) winnings to prize winners? ..................

Yes

Form 990 (2021)

Page 5

Part V

Statements Regarding Other IRS Filings and Tax Compliance (continued)

Enter the number of employees reported on Form W-3, Transmittal of Wage and
Tax Statements, filed for the calendar year ending with or within the year covered by this return ..................

If at least one is reported on line 2a, did the organization file all required federal employment tax returns?
Note. If the sum of lines 1a and 2a is greater than 250, you may be required to e-file. See instructions.

Did the organization have unrelated business gross income of $1,000 or more during the year?...

If “Yes,” has it filed a Form 990-T for this year? If “No” to line 3b, provide an explanation in Schedule O...

At any time during the calendar year, did the organization have an interest in, or a signature or other authority over, a financial account in a foreign country (such as a bank account, securities account, or other financial account)? ..

If "Yes," enter the name of the foreign country: MediumBullet

See instructions for filing requirements for FinCEN Form 114, Report of Foreign Bank and Financial Accounts (FBAR).

Was the organization a party to a prohibited tax shelter transaction at any time during the tax year? ..

Did any taxable party notify the organization that it was or is a party to a prohibited tax shelter transaction?

If "Yes," to line 5a or 5b, did the organization file Form 8886-T? ............

Does the organization have annual gross receipts that are normally greater than $100,000, and did the organization solicit any contributions that were not tax deductible as charitable contributions? ...

If "Yes," did the organization include with every solicitation an express statement that such contributions or gifts were not tax deductible? ......................

Organizations that may receive deductible contributions under section 170(c).

Did the organization receive a payment in excess of $75 made partly as a contribution and partly for goods and services provided to the payor? ....................

If "Yes," did the organization notify the donor of the value of the goods or services provided? .....

Did the organization sell, exchange, or otherwise dispose of tangible personal property for which it was required to file Form 8282? .........................

If "Yes," indicate the number of Forms 8282 filed during the year ....

Did the organization receive any funds, directly or indirectly, to pay premiums on a personal benefit contract?

Did the organization, during the year, pay premiums, directly or indirectly, on a personal benefit contract? ..

If the organization received a contribution of qualified intellectual property, did the organization file Form 8899 as required? ......................

If the organization received a contribution of cars, boats, airplanes, or other vehicles, did the organization file a Form 1098-C? ..........................

Sponsoring organizations maintaining donor advised funds. Did a donor advised fund maintained by the sponsoring organization have excess business holdings at any time during the year? ........

Sponsoring organizations maintaining donor advised funds.

Did the sponsoring organization make any taxable distributions under section 4966?........

Did the sponsoring organization make a distribution to a donor, donor advisor, or related person?...

Section 501(c)(7) organizations. Enter:

Initiation fees and capital contributions included on Part VIII, line 12 ...

10a

Gross receipts, included on Form 990, Part VIII, line 12, for public use of club facilities

10b

Section 501(c)(12) organizations. Enter:

Gross income from members or shareholders .........

11a

Gross income from other sources. (Do not net amounts due or paid to other sources against amounts due or received from them.) ..........

11b

12a

Section 4947(a)(1) non-exempt charitable trusts. Is the organization filing Form 990 in lieu of Form 1041?

12a

If "Yes," enter the amount of tax-exempt interest received or accrued during the year.

12b

Section 501(c)(29) qualified nonprofit health insurance issuers.

Is the organization licensed to issue qualified health plans in more than one state? .........
Note. See the instructions for additional information the organization must report on Schedule O.

13a

Enter the amount of reserves the organization is required to maintain by the states in which the organization is licensed to issue qualified health plans ....

13b

Enter the amount of reserves on hand ............

13c

14a

Did the organization receive any payments for indoor tanning services during the tax year?.....

14a

If "Yes," has it filed a Form 720 to report these payments? If "No," provide an explanation in Schedule O..

14b

Is the organization subject to the section 4960 tax on payment(s) of more than $1,000,000 in remuneration or excess parachute payment(s) during the year? ....................
If "Yes," see the instructions and file Form 4720, Schedule N.

Is the organization an educational institution subject to the section 4968 excise tax on net investment income? ..
If "Yes," complete Form 4720, Schedule O.

Section 501(c)(21) organizations. Did the trust, any disqualified person, or mine operator engage in any activities that would result in the imposition of an excise tax under section 4951, 4952, or 4953? ..
If "Yes," complete Form 6069.

Form 990 (2021)

Page 6

Part VI

Governance, Management, and Disclosure. For each "Yes" response to lines 2 through 7b below, and for a "No" response to lines 8a, 8b, or 10b below, describe the circumstances, processes, or changes in Schedule O. See instructions.

Check if Schedule O contains a response or note to any line in this Part VI..............

Section A. Governing Body and Management

Yes

Enter the number of voting members of the governing body at the end of the tax year

If there are material differences in voting rights among members of the governing body, or if the governing body delegated broad authority to an executive committee or similar committee, explain in Schedule O.

Enter the number of voting members included in line 1a, above, who are independent

Did any officer, director, trustee, or key employee have a family relationship or a business relationship with any other officer, director, trustee, or key employee? .................

Did the organization delegate control over management duties customarily performed by or under the direct supervision of officers, directors or trustees, or key employees to a management company or other person? .

Did the organization make any significant changes to its governing documents since the prior Form 990 was filed? .

Did the organization become aware during the year of a significant diversion of the organization’s assets? .

Did the organization have members or stockholders? ................

Yes

Did the organization have members, stockholders, or other persons who had the power to elect or appoint one or more members of the governing body? ....................

Yes

Are any governance decisions of the organization reserved to (or subject to approval by) members, stockholders, or persons other than the governing body? ...................

Yes

Did the organization contemporaneously document the meetings held or written actions undertaken during the year by the following:

The governing body? .......................

Yes

Each committee with authority to act on behalf of the governing body? ............

Yes

Is there any officer, director, trustee, or key employee listed in Part VII, Section A, who cannot be reached at the organization’s mailing address? If "Yes," provide the names and addresses in Schedule O.......

Section B. Policies (This Section B requests information about policies not required by the Internal Revenue Code.)

Yes

10a

Did the organization have local chapters, branches, or affiliates? ............

10a

If "Yes," did the organization have written policies and procedures governing the activities of such chapters, affiliates, and branches to ensure their operations are consistent with the organization's exempt purposes?

10b

11a

Has the organization provided a complete copy of this Form 990 to all members of its governing body before filing the form? ............................

11a

Describe on Schedule O the process, if any, used by the organization to review this Form 990. .....

12a

Did the organization have a written conflict of interest policy? If "No," go to line 13.......

12a

Yes

Were officers, directors, or trustees, and key employees required to disclose annually interests that could give rise to conflicts? ..........................

12b

Yes

Did the organization regularly and consistently monitor and enforce compliance with the policy? If "Yes," describe on Schedule O how this was done...................

12c

Yes

Did the organization have a written whistleblower policy? ...............

Yes

Did the organization have a written document retention and destruction policy? .........

Yes

Did the process for determining compensation of the following persons include a review and approval by independent persons, comparability data, and contemporaneous substantiation of the deliberation and decision?

The organization’s CEO, Executive Director, or top management official ...........

15a

Yes

Other officers or key employees of the organization ................

15b

Yes

If "Yes" to line 15a or 15b, describe the process on Schedule O. See instructions.

16a

Did the organization invest in, contribute assets to, or participate in a joint venture or similar arrangement with a taxable entity during the year? ......................

16a

If "Yes," did the organization follow a written policy or procedure requiring the organization to evaluate its participation in joint venture arrangements under applicable federal tax law, and take steps to safeguard the organization’s exempt status with respect to such arrangements? ............

16b

Section C. Disclosure

List the states with which a copy of this Form 990 is required to be filed MediumBullet

Section 6104 requires an organization to make its Form 1023 (1024 or 1024-A, if applicable), 990, and 990-T (section 501(c)(3)s only) available for public inspection. Indicate how you made these available. Check all that apply.

Own website Another's website Upon request Other (explain in Schedule O)

Describe in Schedule O whether (and if so, how) the organization made its governing documents, conflict of interest policy, and financial statements available to the public during the tax year.

State the name, address, and telephone number of the person who possesses the organization's books and records:
MediumBullet

FRANCIS LINARDI8722 LOCH RAVEN BLVD TOWSON,MD212862235 (410) 494-2000

Form 990 (2021)

Page 7

Part VII

Compensation of Officers, Directors,Trustees, Key Employees, Highest Compensated Employees, and Independent Contractors

Check if Schedule O contains a response or note to any line in this Part VII..............

Section A. Officers, Directors, Trustees, Key Employees, and Highest Compensated Employees

1a Complete this table for all persons required to be listed. Report compensation for the calendar year ending with or within the organization’s tax year.
RoundBullet

List all of the organization’s current officers, directors, trustees (whether individuals or organizations), regardless of amount
of compensation. Enter -0- in columns (D), (E), and (F) if no compensation was paid.

List all of the organization’s current key employees, if any. See the instructions for definition of "key employee."

List the organization’s five current highest compensated employees (other than an officer, director, trustee or key employee)
who received reportable compensation (box 5 of Form W-2, Form 1099-MISC, and/or box 1 of Form 1099-NEC) of more than $100,000 from the
organization and any related organizations.

List all of the organization’s former officers, key employees, or highest compensated employees who received more than $100,000
of reportable compensation from the organization and any related organizations.

List all of the organization’s former directors or trustees that received, in the capacity as a former director or trustee of the
organization, more than $10,000 of reportable compensation from the organization and any related organizations.

See the instructions for the order in which to list the persons above.

Check this box if neither the organization nor any related organization compensated any current officer, director, or trustee.

(A) Name and title	(B) Average hours per week (list any hours for related organizations below dotted line)	(C) Position (do not check more than one box, unless person is both an officer and a director/trustee)				(D) Reportable compensation from the organization (W-2/1099-MISC/1099-NEC)	(E) Reportable compensation from related organizations (W-2/1099-MISC/1099-NEC)	(F) Estimated amount of other compensation from the organization and related organizations
(A) Name and title
(1) THOMAS PHELAN...................................................................... CHIEF EXECUTIVE OFFICER	30.00 ................. 10.00		X			405,160	0	12,200
(2) KEVIN BINGHAM...................................................................... CHIEF RESULTS OFFICER	30.00 ................. 10.00			X		339,681	0	33,114
(3) PAIGE BECK...................................................................... PRESIDENT	30.00 ................. 10.00		X			215,914	0	12,200
(4) FRANK LINARDI...................................................................... CHIEF FINANCIAL OFFICER	30.00 ................. 10.00		X			153,165	0	15,971
(5) CARMINE D'ALESSANDRO...................................................................... CHIEF LEGAL OFFICER	30.00 ................. 10.00		X			144,506	0	17,737
(6) SHARON ROWELL...................................................................... CHIEF ADMINISTRATIVE OFFICER	30.00 ................. 10.00				X	148,375	0	10,580
(7) SONG HE...................................................................... CHIEF INVESTMENT OFFICER	30.00 ................. 10.00				X	129,545	0	27,053
(8) STEPHEN FISHER...................................................................... MEDICAL CONSULTANT	30.00 ................. 10.00				X	115,440	0	11,427
(9) SUZANNE THOMPSON...................................................................... BOARD CHAIR	1.50 ................. 0.50	X	X			23,244	0	0
(10) FRANKLIN HAJEK...................................................................... DIRECTOR	1.50 ................. 0.50	X				22,699	0	300
(11) MARIA TILDON...................................................................... DIRECTOR (TO JUN '22)	1.50 ................. 0.50	X				22,715	0	224
(12) SPENCER CAVALIER...................................................................... DIRECTOR	1.50 ................. 0.50	X				21,563	0	0
(13) KETURAH MCGHEE...................................................................... DIRECTOR	1.50 ................. 0.50	X				20,819	0	0
(14) MARTIN MADDEN...................................................................... DIRECTOR	1.50 ................. 0.50	X				20,719	0	0
(15) JOHN SCOTT JR...................................................................... VICE CHAIR	1.50 ................. 0.50	X	X			20,719	0	0
(16) JASON SCHUPP...................................................................... DIRECTOR	1.50 ................. 0.50	X				20,719	0	0
(17) THEODORE ALEXANDER III...................................................................... DIRECTOR	1.50 ................. 0.50	X				10,361	0	0

Form 990 (2021)

Page 8

Part VII

Section A. Officers, Directors, Trustees, Key Employees, and Highest Compensated Employees (continued)

(A) Name and title	(B) Average hours per week (list any hours for related organizations below dotted line)	(C) Position (do not check more than one box, unless person is both an officer and a director/trustee)	(D) Reportable compensation from the organization (W-2/1099-MISC/1099-NEC)	(E) Reportable compensation from related organizations (W-2/1099-MISC/1099-NEC)	(F) Estimated amount of other compensation from the organization and related organizations
(A) Name and title
(18) SALLY JAMESON........................................................................ DIRECTOR (FROM JUN '22)	1.50 .......................0.50	X	0	0	0

1b	Sub-Total................
c	Total from continuation sheets to Part VII, Section A....
d	Total (add lines 1b and 1c)...........	1,835,344	0	140,806

Total number of individuals (including but not limited to those listed above) who received more than $100,000 of reportable compensation from the organization MediumBullet

Yes

Did the organization list any former officer, director or trustee, key employee, or highest compensated employee on line 1a? If "Yes," complete Schedule J for such individual ..............

For any individual listed on line 1a, is the sum of reportable compensation and other compensation from the organization and related organizations greater than $150,000? If "Yes," complete Schedule J for such
individual...........................

Yes

Did any person listed on line 1a receive or accrue compensation from any unrelated organization or individual for services rendered to the organization? If "Yes," complete Schedule J for such person ........

Section B. Independent Contractors

Complete this table for your five highest compensated independent contractors that received more than $100,000 of compensation from the organization. Report compensation for the calendar year ending with or within the organization’s tax year.

(A) Name and business address	(B) Description of services	(C) Compensation
THE COOPER HEALTH SYSTEM 1 FEDERAL ST STE 200 CAMDEN,NJ08103	MEDICAL/HEALTH SERVICES	936,547
UNIV OF MD MEDICAL SYSTEM CORP PO BOX 64468 BALTIMORE,MD21264	MEDICAL/HEALTH SERVICES	876,326
EXPRESS SCRIPTS INC ONE EXPRESS WAY MS HQ2E04 ST LOUIS,MO63121	MEDICAL/HEALTH SERVICES	718,160
VGM GROUP INC PO BOX 1860 WATERLOO,IA50704	INVESTMENT SERVICES	648,576
ADVANCED HOME SUPPORT INC 15800 CRABBS BRANCH WAY STE 205 ROCKVILLE,MD20855	MEDICAL/HEALTH SERVICES	588,598
2 Total number of independent contractors (including but not limited to those listed above) who received more than $100,000 of compensation from the organization 69

Form 990 (2021)

Page 9

Part VIII

Statement of Revenue

Check if Schedule O contains a response or note to any line in this Part VIII.............

(A)
Total revenue

(B)
Related or
exempt
function
revenue

(D)
Revenue
excluded from
tax under sections
512 - 514

1a	Federated campaigns..	1a
b	Membership dues..	1b
c	Fundraising events..	1c
d	Related organizations	1d
e	Government grants (contributions)	1e

f	All other contributions, gifts, grants, and similar amounts not included above	1f

g	Noncash contributions included in lines 1a - 1f:$	1g

h Total. Add lines 1a-1f.......

		Business Code
2a	PREMIUMS EARNED	900099	91,276,789	91,276,789
b	INSTALLMENT FEES & NSF CHARGES	900099	180,637	180,637
c
d
e
f	All other program service revenue.
g	Total. Add lines 2a–2f .....		91,457,426

3 Investment income (including dividends, interest, and othersimilar amounts) ......			31,987,109			31,987,109
4 Income from investment of tax-exempt bond proceeds
5 Royalties...........
		(ii) Personal	(i) Real
6a	Gross rents			6a
b	Less: rental expenses			6b
c	Rental income or (loss)			6c
d	Net rental income or (loss).......
		(ii) Other	(i) Securities
7a	Gross amount from sales of assets other than inventory		581,059,283	7a
b	Less: cost or other basis and sales expenses	26,349	570,608,849	7b
c	Gain or (loss)	-26,349	10,450,434	7c
d	Net gain or (loss).........			10,424,085			10,424,085
8a	Gross income from fundraising events (not including $ of contributions reported on line 1c). See Part IV, line 18 ....
			8a
b	Less: direct expenses ...		8b
c	Net income or (loss) from fundraising events..
9a	Gross income from gaming activities. See Part IV, line 19 ...
			9a
b	Less: direct expenses ...		9b
c	Net income or (loss) from gaming activities..
10a	Gross sales of inventory, less returns and allowances ..
			10a
b	Less: cost of goods sold ..		10b
c	Net income or (loss) from sales of inventory..
Business Code			Miscellaneous Revenue
11a	PROCEEDS FROM FIRE INSURANCE		900099	999,986			999,986
b
c
d	All other revenue ....			5,686			5,686
e	Total. Add lines 11a–11d ......			1,005,672
12	Total revenue. See instructions.....			134,874,292	91,457,426	0	43,416,866

Form 990 (2021)

Page 10

Part IX

Statement of Functional Expenses

Section 501(c)(3) and 501(c)(4) organizations must complete all columns. All other organizations must complete column (A).Check if Schedule O contains a response or note to any line in this Part IX..............

Do not include amounts reported on lines 6b, 7b, 8b, 9b, and 10b of Part VIII.		(A) Total expenses	(B) Program service expenses	(C) Management and general expenses	(D) Fundraising expenses

1	Grants and other assistance to domestic organizations and domestic governments. See Part IV, line 21 ....	126,326
2	Grants and other assistance to domestic individuals. See Part IV, line 22 ...........
3	Grants and other assistance to foreign organizations, foreign governments, and foreign individuals. See Part IV, lines 15 and 16. .............
4	Benefits paid to or for members .......
5	Compensation of current officers, directors, trustees, and key employees ...........	1,533,730
6	Compensation not included above, to disqualified persons (as defined under section 4958(f)(1)) and persons described in section 4958(c)(3)(B) .........
7	Other salaries and wages........	14,195,506
8	Pension plan accruals and contributions (include section 401(k) and 403(b) employer contributions) ....	1,066,633
9	Other employee benefits .......	2,156,282
10	Payroll taxes ...........	1,095,739
11	Fees for services (non-employees):
a	Management ......
b	Legal .........	433,807
c	Accounting ...........	50,363
d	Lobbying ...........
e	Professional fundraising services. See Part IV, line 17
f	Investment management fees ......	2,805,036
g	Other (If line 11g amount exceeds 10% of line 25, column (A) amount, list line 11g expenses on Schedule O)	15,148,018
12	Advertising and promotion ....	1,428,385
13	Office expenses .......	1,839,243
14	Information technology ......	1,374,111
15	Royalties ..
16	Occupancy ...........	1,448,654
17	Travel ............	159,755
18	Payments of travel or entertainment expenses for any federal, state, or local public officials .
19	Conferences, conventions, and meetings ....	79,878
20	Interest ...........	445,183
21	Payments to affiliates .......
22	Depreciation, depletion, and amortization ..	3,289,276
23	Insurance ...	434,213
24	Other expenses. Itemize expenses not covered above (List miscellaneous expenses in line 24e. If line 24e amount exceeds 10% of line 25, column (A) amount, list line 24e expenses on Schedule O.)
a	LOSSES	47,791,224
b	TAXES, LICENSES, FEES	4,099,236
c
d
e	All other expenses	231,263
25	Total functional expenses. Add lines 1 through 24e	101,231,861
26	Joint costs. Complete this line only if the organization reported in column (B) joint costs from a combined educational campaign and fundraising solicitation. Check here if following SOP 98-2 (ASC 958-720).

Form 990 (2021)

Page 11

Part X

Balance Sheet

Check if Schedule O contains a response or note to any line in this Part IX..............

				(A) Beginning of year		(B) End of year

1	Cash–non-interest-bearing ........			17,156,257	1	0
2	Savings and temporary cash investments .........			68,610,724	2	0
3	Pledges and grants receivable, net ......				3	0
4	Accounts receivable, net .............			54,308,368	4	0
5	Loans and other receivables from any current or former officer, director, trustee, key employee, creator or founder, substantial contributor, or 35% controlled entity or family member of any of these persons .......
					5	0
6	Loans and other receivables from other disqualified persons (as defined under section 4958(f)(1)), and persons described in section 4958(c)(3)(B) ...
					6	0
7	Notes and loans receivable, net ...........				7	0
8	Inventories for sale or use ............				8	0
9	Prepaid expenses and deferred charges ......				9	0
10a	Land, buildings, and equipment: cost or other basis. Complete Part VI of Schedule D	10a	0
b	Less: accumulated depreciation	10b	0	8,567,326	10c	0
11	Investments—publicly traded securities .			2,220,076,387	11	0
12	Investments—other securities. See Part IV, line 11 .....			107,245,467	12	0
13	Investments—program-related. See Part IV, line 11 ..				13	0
14	Intangible assets ...............				14	0
15	Other assets. See Part IV, line 11 ...........			36,367,171	15	0
16	Total assets. Add lines 1 through 15 (must equal line 33)...			2,512,331,700	16	0

17	Accounts payable and accrued expenses .....	27,707,515	17	0
18	Grants payable ...		18
19	Deferred revenue .........	79,969,853	19	0
20	Tax-exempt bond liabilities .........		20
21	Escrow or custodial account liability. Complete Part IV of Schedule D		21
22	Loans and other payables to any current or former officer, director, trustee, key employee, creator or founder, substantial contributor, or 35% controlled entity or family member of any of these persons .........
			22
23	Secured mortgages and notes payable to unrelated third parties ..		23
24	Unsecured notes and loans payable to unrelated third parties ..		24
25	Other liabilities (including federal income tax, payables to related third parties, and other liabilities not included on lines 17 - 24). Complete Part X of Schedule D	1,267,122,288	25	0
26	Total liabilities. Add lines 17 through 25..	1,374,799,656	26	0

	Organizations that follow FASB ASC 958, check here and complete lines 27, 28, 32, and 33.
27	Net assets without donor restrictions ..........	1,137,532,044	27	0
28	Net assets with donor restrictions ...........		28
	Organizations that do not follow FASB ASC 958, check here and complete lines 29 through 33.
29	Capital stock or trust principal, or current funds .....		29
30	Paid-in or capital surplus, or land, building or equipment fund ...		30
31	Retained earnings, endowment, accumulated income, or other funds		31
32	Total net assets or fund balances ...........	1,137,532,044	32	0
33	Total liabilities and net assets/fund balances ........	2,512,331,700	33	0

Form 990 (2021)

Page 12

Part XI

Reconcilliation of Net Assets

Check if Schedule O contains a response or note to any line in this Part XI..............

Total revenue (must equal Part VIII, column (A), line 12) ............

134,874,292

Total expenses (must equal Part IX, column (A), line 25) ............

101,231,861

Revenue less expenses. Subtract line 2 from line 1 ..............

33,642,431

Net assets or fund balances at beginning of year (must equal Part X, line 32, column (A)) ..

1,137,532,044

Net unrealized gains (losses) on investments ...............

-72,542,310

Donated services and use of facilities .................

Investment expenses .....................

Prior period adjustments .....................

Other changes in net assets or fund balances (explain in Schedule O) ........

-1,098,632,165

Net assets or fund balances at end of year. Combine lines 3 through 9 (must equal Part X, line 32, column (B))

Part XII

Financial Statements and Reporting

Check if Schedule O contains a response or note to any line in this Part XII.............

Yes

Accounting method used to prepare the Form 990: Cash Accrual Other
If the organization changed its method of accounting from a prior year or checked "Other," explain on
Schedule O.

Were the organization’s financial statements compiled or reviewed by an independent accountant?

If ‘Yes,’ check a box below to indicate whether the financial statements for the year were compiled or reviewed on a separate basis, consolidated basis, or both:

Separate basis Consolidated basis Both consolidated and separate basis

Were the organization’s financial statements audited by an independent accountant?

Yes

If ‘Yes,’ check a box below to indicate whether the financial statements for the year were audited on a separate basis, consolidated basis, or both:

Separate basis Consolidated basis Both consolidated and separate basis

If "Yes," to line 2a or 2b, does the organization have a committee that assumes responsibility for oversight of the audit, review, or compilation of its financial statements and selection of an independent accountant?

Yes

If the organization changed either its oversight process or selection process during the tax year, explain in Schedule O.

As a result of a federal award, was the organization required to undergo an audit or audits as set forth in the Single Audit Act and OMB Circular A-133?

If "Yes," did the organization undergo the required audit or audits? If the organization did not undergo the required audit or audits, explain why in Schedule O and describe any steps taken to undergo such audits.

Form 990 (2021)

Additional Data

Software ID:
Software Version:

Form 990, Special Condition Description:

Special Condition Description

- TIN:

SCHEDULE D
(Form 990)

Department of the Treasury
Internal Revenue Service

Supplemental Financial Statements

Complete if the organization answered "Yes," on Form 990,
Part IV, line 6, 7, 8, 9, 10, 11a, 11b, 11c, 11d, 11e, 11f, 12a, or 12b.
SchDMd Bullet

Attach to Form 990.
SchDMd Bullet

Go to www.irs.gov/Form990 for instructions and the latest information.

OMB No. 1545-0047

2021

Open to Public Inspection

Name of the organization

CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Employer identification number

46-1056754

Part I

Organizations Maintaining Donor Advised Funds or Other Similar Funds or Accounts. Complete if the organization answered "Yes" on Form 990, Part IV, line 6.

		(a) Donor advised funds	(b) Funds and other accounts
1	Total number at end of year .........
2	Aggregate value of contributions to (during year)
3	Aggregate value of grants from (during year)
4	Aggregate value at end of year ........

Did the organization inform all donors and donor advisors in writing that the assets held in donor advised funds are the organization’s property, subject to the organization’s exclusive legal control? ............

Yes No

Did the organization inform all grantees, donors, and donor advisors in writing that grant funds can be used only for charitable purposes and not for the benefit of the donor or donor advisor, or for any other purpose conferring impermissible private benefit? ...................................

Yes No

Part II

Conservation Easements.
Complete if the organization answered "Yes" on Form 990, Part IV, line 7.

Purpose(s) of conservation easements held by the organization (check all that apply).

Preservation of land for public use (e.g., recreation or education) Preservation of an historically important land area

Protection of natural habitat Preservation of a certified historic structure

Preservation of open space

Complete lines 2a through 2d if the organization held a qualified conservation contribution in the form of a conservation easement on the last day of the tax year.


a	Total number of conservation easements ......................	2a
b	Total acreage restricted by conservation easements ....................	2b
c	Number of conservation easements on a certified historic structure included in (a) .....	2c
d	Number of conservation easements included in (c) acquired after 7/25/06, and not on a historic structure listed in the National Register ...	2d

Number of conservation easements modified, transferred, released, extinguished, or terminated by the organization during the
tax year SchDMd Bullet

Number of states where property subject to conservation easement is located SchDMd Bullet

Does the organization have a written policy regarding the periodic monitoring, inspection, handling of violations, and enforcement of the conservation easements it holds? ............

Yes No

Staff and volunteer hours devoted to monitoring, inspecting, handling of violations, and enforcing conservation easements during the year
SchDMd Bullet

Amount of expenses incurred in monitoring, inspecting, handling of violations, and enforcing conservation easements during the year
SchDMd Bullet

Does each conservation easement reported on line 2(d) above satisfy the requirements of section 170(h)(4)(B)(i) and section 170(h)(4)(B)(ii)? .............................

Yes No

In Part XIII, describe how the organization reports conservation easements in its revenue and expense statement, and
balance sheet, and include, if applicable, the text of the footnote to the organization’s financial statements that describes
the organization’s accounting for conservation easements.

Part III

Organizations Maintaining Collections of Art, Historical Treasures, or Other Similar Assets.
Complete if the organization answered "Yes" on Form 990, Part IV, line 8.

If the organization elected, as permitted under FASB ASC 958, not to report in its revenue statement and balance sheet works of art, historical treasures, or other similar assets held for public exhibition, education, or research in furtherance of public service, provide, in Part XIII, the text of the footnote to its financial statements that describes these items.

If the organization elected, as permitted under FASB ASC 958, to report in its revenue statement and balance sheet works of art, historical treasures, or other similar assets held for public exhibition, education, or research in furtherance of public service, provide the following amounts relating to these items:

(i)

Revenue included on Form 990, Part VIII, line 1 ......................... SchDMd Bullet

(ii)

Assets included in Form 990, Part X ............................... SchDMd Bullet

If the organization received or held works of art, historical treasures, or other similar assets for financial gain, provide the
following amounts required to be reported under FASB ASC 958 relating to these items:

Revenue included on Form 990, Part VIII, line 1 .......................... SchDMd Bullet

Assets included in Form 990, Part X ............................... SchDMd Bullet

For Paperwork Reduction Act Notice, see the Instructions for Form 990.

Cat. No. 52283D

Schedule D (Form 990) 2021

Page 2

Part III

Organizations Maintaining Collections of Art, Historical Treasures, or Other Similar Assets (continued)

Using the organization’s acquisition, accession, and other records, check any of the following that are a significant use of its collection items (check all that apply):

Public exhibition

Loan or exchange programs

Scholarly research

Other

Preservation for future generations

Provide a description of the organization’s collections and explain how they further the organization’s exempt purpose in
Part XIII.

During the year, did the organization solicit or receive donations of art, historical treasures or other similar
assets to be sold to raise funds rather than to be maintained as part of the organization’s collection?...

Yes No

Part IV

Escrow and Custodial Arrangements. Complete if the organization answered "Yes" on Form 990, Part IV, line 9, or reported an amount on Form 990, Part X, line 21.

Is the organization an agent, trustee, custodian or other intermediary for contributions or other assets not
included on Form 990, Part X? ....................................

Yes No


b	If "Yes," explain the arrangement in Part XIII and complete the following table:		Amount
c	Beginning balance .............................	1c
d	Additions during the year ............................	1d
e	Distributions during the year ..........................	1e
f	Ending balance ................................	1f

Did the organization include an amount on Form 990, Part X, line 21, for escrow or custodial account liability? ...

Yes No

If "Yes," explain the arrangement in Part XIII. Check here if the explanation has been provided in Part XIII ....

Part V

Endowment Funds.
Complete if the organization answered "Yes" on Form 990, Part IV, line 10.

		(a) Current year	(b) Prior year	(c) Two years back	(d) Three years back	(e) Four years back

1a	Beginning of year balance ....
b	Contributions ...
c	Net investment earnings, gains, and losses
d	Grants or scholarships ...
e	Other expenditures for facilities and programs ...
f	Administrative expenses ....
g	End of year balance ......

Provide the estimated percentage of the current year end balance (line 1g, column (a)) held as:

Board designated or quasi-endowment SchDMd Bullet

Permanent endowment SchDMd Bullet

Term endowment SchDMd Bullet

The percentages on lines 2a, 2b, and 2c should equal 100%.

Are there endowment funds not in the possession of the organization that are held and administered for the
organization by:

Yes

(i) Unrelated organizations .................

3a(i)

(ii) Related organizations .................

3a(ii)

If "Yes" on 3a(ii), are the related organizations listed as required on Schedule R? .........

Describe in Part XIII the intended uses of the organization's endowment funds.

Part VI

Land, Buildings, and Equipment.
Complete if the organization answered "Yes" on Form 990, Part IV, line 11a. See Form 990, Part X, line 10.

Description of property		(a) Cost or other basis (investment)	(b) Cost or other basis (other)	(c) Accumulated depreciation	(d) Book value

1a	Land .....
b	Buildings ....
c	Leasehold improvements
d	Equipment ....
e	Other .....
Total. Add lines 1a through 1e. (Column (d) must equal Form 990, Part X, column (B), line 10(c).)..		0

Schedule D (Form 990) 2021

Page 3

Part VII

Investments - Other Securities.
Complete if the organization answered "Yes" on Form 990, Part IV, line 11b. See Form 990, Part X, line 12.

(a) Description of security or category (including name of security)	(b) Book value	(c) Method of valuation: Cost or end-of-year market value
(1) Financial derivatives.........
(2) Closely-held equity interests........
(3)Other
(A)
(B)
(C)
(D)
(E)
(F)
(G)
(H)
Total. (Column (b) must equal Form 990, Part X, col. (B) line 12.)

Part VIII

Investments - Program Related. Complete if the organization answered 'Yes' on Form 990, Part IV, line 11c. See Form 990, Part X, line 13.

(a) Description of investment	(b) Book value	(c) Method of valuation: Cost or end-of-year market value

(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
Total. (Column (b) must equal Form 990, Part X, col.(B) line 13.)

Part IX

Other Assets.
Complete if the organization answered 'Yes' on Form 990, Part IV, line 11d. See Form 990, Part X, line 15.

(a) Description				(b) Book value

(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
Total. (Column (b) must equal Form 990, Part X, col.(B) line 15.)...........

Part X

Other Liabilities.
Complete if the organization answered 'Yes' on Form 990, Part IV, line 11e or 11f. See Form 990, Part X, line 25.

1.(a) Description of liability	(b) Book value
(1) Federal income taxes

(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
Total. (Column (b) must equal Form 990, Part X, col.(B) line 25.)
2. Liability for uncertain tax positions. In Part XIII, provide the text of the footnote to the organization's financial statements that reports the organization's liability for uncertain tax positions under FIN 48 (ASC 740). Check here if the text of the footnote has been provided in Part XIII

Schedule D (Form 990) 2021

Page 4

Part XI Reconciliation of Revenue per Audited Financial Statements With Revenue per Return. Complete if the organization answered 'Yes' on Form 990, Part IV, line 12a.
1	Total revenue, gains, and other support per audited financial statements .......		1
2	Amounts included on line 1 but not on Form 990, Part VIII, line 12:
a	Net unrealized gains (losses) on investments ....	2a
b	Donated services and use of facilities .........	2b
c	Recoveries of prior year grants ...........	2c
d	Other (Describe in Part XIII.) ............	2d
e	Add lines 2a through 2d .....................		2e
3	Subtract line 2e from line 1..................		3
4	Amounts included on Form 990, Part VIII, line 12, but not on line 1:
a	Investment expenses not included on Form 990, Part VIII, line 7b .	4a
b	Other (Describe in Part XIII.) ...........	4b
c	Add lines 4a and 4b....................		4c
5	Total revenue. Add lines 3 and 4c. (This must equal Form 990, Part I, line 12.) ......		5

Part XII Reconciliation of Expenses per Audited Financial Statements With Expenses per Return. Complete if the organization answered 'Yes' on Form 990, Part IV, line 12a.
1	Total expenses and losses per audited financial statements ...........		1
2	Amounts included on line 1 but not on Form 990, Part IX, line 25:
a	Donated services and use of facilities .........	2a
b	Prior year adjustments ............	2b
c	Other losses ................	2c
d	Other (Describe in Part XIII.) ............	2d
e	Add lines 2a through 2d....................		2e
3	Subtract line 2e from line 1...................		3
4	Amounts included on Form 990, Part IX, line 25, but not on line 1:
a	Investment expenses not included on Form 990, Part VIII, line 7b ..	4a
b	Other (Describe in Part XIII.) ............	4b
c	Add lines 4a and 4b.....................		4c
5	Total expenses. Add lines 3 and 4c. (This must equal Form 990, Part I, line 18.) ......		5

Part XIII

Supplemental Information

Provide the descriptions required for Part II, lines 3, 5, and 9; Part III, lines 1a and 4; Part lV, lines 1b and 2b; Part V, line 4; Part X, line 2; Part XI, lines 2d and 4b; and Part XII, lines 2d and 4b. Also complete this part to provide any additional information.

Return Reference	Explanation
PART X, LINE 2:	CHESAPEAKE DOES NOT HAVE ANY UNCERTAIN TAX POSITIONS THAT ARE MATERIAL TO THE FINANCIAL STATEMENTS AS OF DECEMBER 31, 2022.

Schedule D (Form 990) 2021

Additional Data

Software ID:
Software Version:

- TIN:

Note: To capture the full content of this document, please select landscape mode (11" x 8.5") when printing.

Schedule I
(Form 990)

Department of the Treasury
Internal Revenue Service

Grants and Other Assistance to Organizations,
Governments and Individuals in the United States

Complete if the organization answered "Yes," on Form 990, Part IV, line 21 or 22.
lBullet

Attach to Form 990.
lBullet

Go to www.irs.gov/Form990 for the latest information.

OMB No. 1545-0047

2022

Open to Public
Inspection

Name of the organization
CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Employer identification number
46-1056754

Part I

General Information on Grants and Assistance

Does the organization maintain records to substantiate the amount of the grants or assistance, the grantees' eligibility for the grants or assistance, and
the selection criteria used to award the grants or assistance? ........................

Yes No

Describe in Part IV the organization's procedures for monitoring the use of grant funds in the United States.

Part II

Grants and Other Assistance to Domestic Organizations and Domestic Governments. Complete if the organization answered "Yes" on Form 990, Part IV, line 21, for any recipient

that received more than $5,000. Part II can be duplicated if additional space is needed.

(a) Name and address of organization or government	(b) EIN	(c) IRC section (if applicable)	(d) Amount of cash grant	(h) Purpose of grant or assistance
(1) UNITED WAY OF CENTRAL MARYLAND 1800 WASHINGTON BLVD STE 340 BALTIMORE,MD21230	52-0591543	501(C)(3)	35,072	GENERAL SUPPORT
(2) AMERICAS CHARITIES 14200 PARK MEADOW DR STE 330S CHANTILLY,VA20151	54-1517707	501(C)(3)	13,582	GENERAL SUPPORT
(3) ASSOCIATED BLACK CHARITIES 2 HAMILL RD STE 359 WEST QUAD BALTIMORE,MD21201	52-1427774	501(C)(3)	10,000	CHARITY GOLF EVENT
(4) BALTIMORE SYMPHONY ORCHESTRA 1212 CATHEDRAL ST BALTIMORE,MD21201	52-0629696	501(C)(3)	10,000	GENERAL SUPPORT
(5) FRANCISCAN CENTER INC 101 W 23RD ST BALTIMORE,MD21218	52-1164260	501(C)(3)	7,800	CHARITY GOLF EVENT

Enter total number of section 501(c)(3) and government organizations listed in the line 1 table ................. Bullet Image

Enter total number of other organizations listed in the line 1 table ........................ . Bullet Image

For Paperwork Reduction Act Notice, see the Instructions for Form 990.

Cat. No. 50055P

Schedule I (Form 990) 2022

Page 2

Part III

Grants and Other Assistance to Domestic Individuals. Complete if the organization answered "Yes" on Form 990, Part IV, line 22.
Part III can be duplicated if additional space is needed.

(a) Type of grant or assistance	(b) Number of recipients	(c) Amount of cash grant	(d) Amount of noncash assistance	(e) Method of valuation (book, FMV, appraisal, other)	(f) Description of noncash assistance

(1)
(2)
(3)
(4)
(5)
(6)
(7)

Part IV

Supplemental Information. Provide the information required in Part I, line 2; Part III, column (b); and any other additional information.

Return Reference	Explanation
PART I, LINE 2:	CHESAPEAKE OCCASIONALLY MAKES SMALL CHARITABLE CONTRIBUTIONS AND GRANTS TO 501(C)(3)S AS A WAY OF GIVING BACK TO THE COMMUNITY. GRANTS ARE REVIEWED AND APPROVED BY AN INTERNAL COMMITTEE.

Schedule I (Form 990) 2022

Additional Data

Software ID:
Software Version:

- TIN:

Schedule J
(Form 990)

Department of the Treasury
Internal Revenue Service

Compensation Information

For certain Officers, Directors, Trustees, Key Employees, and Highest
Compensated Employees
SchJMediumBullet

Complete if the organization answered "Yes" on Form 990, Part IV, line 23.
SchJMediumBullet

Attach to Form 990.
SchJMediumBullet

Go to www.irs.gov/Form990 for instructions and the latest information.

OMB No. 1545-0047

2022

Open to Public Inspection

Name of the organization

CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Employer identification number

46-1056754

Part I

Questions Regarding Compensation

Yes

Check the appropiate box(es) if the organization provided any of the following to or for a person listed on Form
990, Part VII, Section A, line 1a. Complete Part III to provide any relevant information regarding these items.

First-class or charter travel Housing allowance or residence for personal use

Travel for companions Payments for business use of personal residence

Tax idemnification and gross-up payments Health or social club dues or initiation fees

Discretionary spending account Personal services (e.g., maid, chauffeur, chef)

If any of the boxes on Line 1a are checked, did the organization follow a written policy regarding payment or reimbursement or provision of all of the expenses described above? If "No," complete Part III to explain .....

Did the organization require substantiation prior to reimbursing or allowing expenses incurred by all
directors, trustees, officers, including the CEO/Executive Director, regarding the items checked on Line 1a? ....

Indicate which, if any, of the following the filing organization used to establish the compensation of the
organization's CEO/Executive Director. Check all that apply. Do not check any boxes for methods
used by a related organization to establish compensation of the CEO/Executive Director, but explain in Part III.

Compensation committee Written employment contract

Independent compensation consultant Compensation survey or study

Form 990 of other organizations Approval by the board or compensation committee

During the year, did any person listed on Form 990, Part VII, Section A, line 1a, with respect to the filing organization or a related organization:

Receive a severance payment or change-of-control payment? .............

Participate in, or receive payment from, a supplemental nonqualified retirement plan? .........

Participate in, or receive payment from, an equity-based compensation arrangement? .........

If "Yes" to any of lines 4a-c, list the persons and provide the applicable amounts for each item in Part III.

Only 501(c)(3), 501(c)(4), and 501(c)(29) organizations must complete lines 5-9.

For persons listed on Form 990, Part VII, Section A, line 1a, did the organization pay or accrue any
compensation contingent on the revenues of:

The organization? ....................

Any related organization? .......................

If "Yes," on line 5a or 5b, describe in Part III.

For persons listed on Form 990, Part VII, Section A, line 1a, did the organization pay or accrue any
compensation contingent on the net earnings of:

The organization? ..................

Any related organization? ......................

If "Yes," on line 6a or 6b, describe in Part III.

For persons listed on Form 990, Part VII, Section A, line 1a, did the organization provide any nonfixed
payments not described in lines 5 and 6? If "Yes," describe in Part III ............

Were any amounts reported on Form 990, Part VII, paid or accured pursuant to a contract that was
subject to the initial contract exception described in Regulations section 53.4958-4(a)(3)? If "Yes," describe
in Part III ..........................

If "Yes" on line 8, did the organization also follow the rebuttable presumption procedure described in Regulations section 53.4958-6(c)? .........................

For Paperwork Reduction Act Notice, see the Instructions for Form 990.

Cat. No. 50053T

Schedule J (Form 990) 2022

Page 2

Part II

Officers, Directors, Trustees, Key Employees, and Highest Compensated Employees. Use duplicate copies if additional space is needed.

For each individual whose compensation must be reported on Schedule J, report compensation from the organization on row (i) and from related organizations, described in the
instructions, on row (ii). Do not list any individuals that are not listed on Form 990, Part VII.
Note. The sum of columns (B)(i)-(iii) for each listed individual must equal the total amount of Form 990, Part VII, Section A, line 1a, applicable column (D) and (E) amounts for that individual.

(A) Name and Title		(B) Breakdown of W-2, 1099-MISC compensation, and/or 1099-NEC			(C) Retirement and other deferred compensation	(D) Nontaxable benefits	(E) Total of columns (B)(i)-(D)	(F) Compensation in column (B) reported as deferred on prior Form 990
(A) Name and Title		(i) Base compensation	(ii) Bonus & incentive compensation	(iii) Other reportable compensation	(C) Retirement and other deferred compensation	(D) Nontaxable benefits	(E) Total of columns (B)(i)-(D)
1THOMAS PHELAN CHIEF EXECUTIVE OFFICER	(i) (ii)	325,364 ------------- 0	77,758 ------------- 0	2,038 ------------- 0	12,200 ------------- 0	0 ------------- 0	417,360 ------------- 0	0 ------------- 0
2KEVIN BINGHAM CHIEF RESULTS OFFICER	(i) (ii)	243,674 ------------- 0	90,000 ------------- 0	6,007 ------------- 0	12,200 ------------- 0	20,914 ------------- 0	372,795 ------------- 0	0 ------------- 0
3PAIGE BECK PRESIDENT	(i) (ii)	204,471 ------------- 0	8,433 ------------- 0	3,010 ------------- 0	12,200 ------------- 0	0 ------------- 0	228,114 ------------- 0	0 ------------- 0
4FRANK LINARDI CHIEF FINANCIAL OFFICER	(i) (ii)	139,033 ------------- 0	6,112 ------------- 0	8,020 ------------- 0	7,211 ------------- 0	8,760 ------------- 0	169,136 ------------- 0	0 ------------- 0
5CARMINE D'ALESSANDRO CHIEF LEGAL OFFICER	(i) (ii)	132,126 ------------- 0	5,716 ------------- 0	6,664 ------------- 0	8,688 ------------- 0	9,049 ------------- 0	162,243 ------------- 0	0 ------------- 0
6SHARON ROWELL CHIEF ADMINISTRATIVE OFFICER	(i) (ii)	138,603 ------------- 0	6,091 ------------- 0	3,681 ------------- 0	10,580 ------------- 0	0 ------------- 0	158,955 ------------- 0	0 ------------- 0
7SONG HE CHIEF INVESTMENT OFFICER	(i) (ii)	123,999 ------------- 0	5,546 ------------- 0	0 ------------- 0	9,878 ------------- 0	17,175 ------------- 0	156,598 ------------- 0	0 ------------- 0

Schedule J (Form 990) 2022

Page 3

Part III

Supplemental Information

Provide the information, explanation, or descriptions required for Part I, lines 1a, 1b, 3, 4a, 4b, 4c, 5a, 5b, 6a, 6b, 7, and 8, and for Part II. Also complete this part for any additional information.

Return Reference	Explanation

Schedule J (Form 990) 2022

Additional Data

Software ID:
Software Version:

- TIN:

Note: To capture the full content of this document, please select landscape mode (11" x 8.5") when printing.

SCHEDULE N
(Form 990)

Department of the Treasury
Internal Revenue Service

Liquidation, Termination, Dissolution, or Significant Disposition of Assets
bullet

Complete if the organization answered "Yes" on Form 990, Part IV, lines 31 or 32; or Form 990-EZ, line 36.
bullet

Attach certified copies of any articles of dissolution, resolutions, or plans.
bullet

Attach to Form 990 or 990-EZ.
bullet

Go to www.irs.gov/Form990 for the latest information.

OMB No. 1545-0047

2022

Open to Public
Inspection

Name of the organization
CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Employer identification number
46-1056754

Part I

Liquidation, Termination, or Dissolution. Complete this part if the organization answered "Yes" on Form 990, Part IV, line 31, or Form 990-EZ, line 36. Part I can be duplicated if additional space is needed.

1(a) Description of asset(s) distributed or transaction expenses paid	(b) Date of distribution	(c) Fair market value of asset(s) distributed or amount of transaction expenses	(d) Method of determining FMV for asset(s) distributed or transaction expenses	(e) EIN of recipient	(f) Name and address of recipient	(g) IRC section of recipient(s) (if tax-exempt) or type of entity
NET ASSETS OF ORGANIZATION	06-30-2022	1,098,271,934	BOOK VALUE AT TRANSFER DATE	46-1056754	CHEAPEAKE EMPLOYERS' INSURANCE COMPANY 8722 LOCH RAVEN BOULEVARD TOWSON,MD212862235	C-CORP

Yes

Did or will any officer, director, trustee, or key employee of the organization:

Become a director or trustee of a successor or transferee organization? ...........................

Yes

Become an employee of, or independent contractor for, a successor or transferee organization? .....................

Yes

Become a direct or indirect owner of a successor or transferee organization? .....................

Receive, or become entitled to, compensation or other similar payments as a result of the organization's liquidation, termination, or dissolution? ........

If the organization answered "Yes" to any of the questions on lines 2a through 2d, provide the name of the person involved and explain in Part III. bullet

For Paperwork Reduction Act Notice, see the Instructions for Form 990.

Cat. No. 50087Z

Schedule N (Form 990) (2022)

Page 2

Part I

Liquidation, Termination, or Dissolution (continued)

Note. If the organization distributed all of its assets during the tax year, then Form 990, Part X, column (B), line 16 (Total assets), and line 26 (Total liabilities), should equal -0-.

Yes

Did the organization distribute its assets in accordance with its governing instrument(s)? If "No," describe in Part III .............

Is the organization required to notify the attorney general or other appropriate state official of its intent to dissolve, liquidate, or terminate? ......

If "Yes," did the organization provide such notice? .....................

Did the organization discharge or pay all of its liabilities in accordance with state laws? .....................

Did the organization have any tax-exempt bonds outstanding during the year? .....................

If "Yes" on line 6a, did the organization discharge or defease all of its tax-exempt bond liabilities during the tax year in accordance with the Internal Revenue Code and state laws?

If "Yes" on line 6b, describe in Part III how the organization defeased or otherwise settled these liabilities. If "No" on line 6b, explain in Part III.

Part II

Sale, Exchange, Disposition, or Other Transfer of More Than 25% of the Organization's Assets. Complete this part if the organization answered "Yes" on Form 990, Part IV, line 32, or Form 990-EZ, line 36. Part II can be duplicated if additional space is needed.

1(a) Description of asset(s) distributed or transaction expenses paid	(b) Date of distribution	(c) Fair market value of asset(s) distributed or amount of transaction expenses	(d) Method of determining FMV for asset(s) distributed or transaction expenses	(e) EIN of recipient	(f) Name and address of recipient	(g) IRC section of recipient(s) (if tax-exempt) or type of entity

Yes

Did or will any officer, director, trustee, or key employee of the organization:

Become a director or trustee of a successor or transferee organization? .........................

Yes

Become an employee of, or independent contractor for, a successor or transferee organization? .....................

Yes

Become a direct or indirect owner of a successor or transferee organization? .....................

Receive, or become entitled to, compensation or other similar payments as a result of the organization's significant disposition of assets? ........

If the organization answered "Yes" to any of the questions on lines 2a through 2d, provide the name of the person involved and explain in Part III. bullet

For Paperwork Reduction Act Notice, see the Instructions for Form 990.

Cat. No. 50087Z

Schedule N (Form 990) (2022)

Page 3

Part III

Supplemental Information. Provide the information required by Part I, lines 2e and 6c, and Part II, line 2e. Also complete this part to provide any additional information.

Return Reference	Explanation

PART I, LINE 2E:	PERSON(S) INVOLVED: THOMAS PHELAN; CHIEF EXECUTIVE OFFICERPAIGE BECK; PRESIDENTFRANK LINARDI; CHIEF FINANCIAL OFFICERCARMINE D'ALESSANDRO; CHIEF LEGAL OFFICERSUZANNE THOMPSON; BOARD CHAIRFRANKLIN HAJEK; DIRECTORSPENCER CAVALIER; DIRECTORKETURAH MCGHEE; DIRECTORMARTIN MADDEN; DIRECTORJOHN SCOTT JR; VICE CHAIRJASON SCHUPP; DIRECTORTHEODORE ALEXANDER III; DIRECTORSALLY JAMESON; DIRECTOR
PART I, LINE 2E:	EXPLANATION OF INVOLVEMENT: THESE INDIVIDUALS' POSITIONS WITH THE ORGANIZATION DID NOT CHANGE DUE TO THE RELINQUISHMENT OF NON-PROFIT STATUS BY THE ORGANIZATION.
PART I:	AT THE START OF THE TAX PERIOD COVERED BY THIS RETURN, THE ORGANIZATIONOPERATED AS A NON-PROFIT, NON-STOCK CORPORATION. PRIOR TO 2020, THEBOARD OF DIRECTORS WAS APPOINTED BY THE GOVERNOR OF THE STATE OFMARYLAND. THE BOARD OF DIRECTORS IS COMPRISED OF NINE MEMBERS WHOAPPOINT A CHIEF EXECUTIVE OFFICER TO ASSIST THEM IN OPERATING ANDADMINISTERING CHESAPEAKE. BEGINNING IN 2020, THE CHESAPEAKE BOARD OFDIRECTORS ELECTION PROCESS BEGAN TRANSITIONING TO POLICYHOLDERELECTION, WHICH WAS COMPLETED IN JUNE 2022. EFFECTIVE JULY 1, 2022,CHESAPEAKE BECAME A TAXABLE ENTITY FOR FEDERAL INCOME TAX PURPOSES.PRIOR TO JUNE 30, 2022, CHESAPEAKE WAS EXEMPT FROM FEDERAL INCOME TAXESUNDER 501(C)(27) OF THE INTERNAL REVENUE CODE. BEGINNING WITH THEINITIAL SHORT YEAR BEGINNING JULY 1ST, 2022 AND ENDING DECEMBER 31ST,2022, THE ORGANIZATION REPORTS THEIR ACTIVITY ON FORM 1120-PC, U.S.PROPERTY AND CASUALTY INSURANCE COMPANY TAX RETURN, AND IS NO LONGERREQUIRED TO FILE FORM 990.BECAUSE THE ORGANIZATION IS NO LONGER REQUIRED TO FILE FORM 990, IN ACCORDANCE WITH IRS INSTRUCTIONS, THE ORGANIZATION IS FILING SCHEDULE L TO SHOW THE ENTIRE NET ASSET BALANCE OF THE ORGANIZATION BEING TRANSFERRED TO ITSELF, AND THE ENDING BALANCE SHEET OF THE ORGANIZATION IS SHOWING ZERO NET ASSETS AS OF YEAR END. THE ORGANIZATION DID NOT CEASE TO EXIST, BUT RATHER CONTINUES TO OPERATE AS A FOR-PROFIT ENTITY.BECAUSE THIS TRANSACTION REPRESENTS A RELINQUISHMENT OF EXEMPT STATUS AND NOT A TERMINATION OF THE ORGANIZATION, SCHEDULE N, PART I, LINES 3-6 HAVE BEEN ANSWERED "NO OR LEFT BLANK, AS APPROPRIATE.

Schedule N (Form 990) (2022)

Additional Data

Software ID:
Software Version:

- TIN:

SCHEDULE O
(Form 990)

Department of the Treasury
Internal Revenue Service

Supplemental Information to Form 990 or 990-EZ

Complete to provide information for responses to specific questions on
Form 990 or 990-EZ or to provide any additional information.
MediumBullet

Attach to Form 990 or 990-EZ.
MediumBullet

Go to www.irs.gov/Form990 for the latest information.

OMB No. 1545-0047

2021

Open to Public
Inspection

Name of the organization

CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Employer identification number

46-1056754

Return Reference	Explanation
FORM 990, HEADING, ITEMS A-B:	AT THE START OF THE TAX PERIOD COVERED BY THIS RETURN, THE ORGANIZATION OPERATED AS A NON-PROFIT, NON-STOCK CORPORATION. PRIOR TO 2020, THE BOARD OF DIRECTORS WAS APPOINTED BY THE GOVERNOR OF THE STATE OF MARYLAND. THE BOARD OF DIRECTORS IS COMPRISED OF NINE MEMBERS WHO APPOINT A CHIEF EXECUTIVE OFFICER TO ASSIST THEM IN OPERATING AND ADMINISTERING CHESAPEAKE. BEGINNING IN 2020, THE CHESAPEAKE BOARD OF DIRECTORS ELECTION PROCESS BEGAN TRANSITIONING TO POLICYHOLDER ELECTION, WHICH WAS COMPLETED IN JUNE 2022. EFFECTIVE JULY 1, 2022, CHESAPEAKE BECAME A TAXABLE ENTITY FOR FEDERAL INCOME TAX PURPOSES. PRIOR TO JUNE 30, 2022, CHESAPEAKE WAS EXEMPT FROM FEDERAL INCOME TAXES UNDER 501(C)(27) OF THE INTERNAL REVENUE CODE. BEGINNING WITH THE INITIAL SHORT YEAR BEGINNING JULY 1ST, 2022 AND ENDING DECEMBER 31ST, 2022, THE ORGANIZATION REPORTS THEIR ACTIVITY ON FORM 1120-PC, U.S. PROPERTY AND CASUALTY INSURANCE COMPANY TAX RETURN, AND IS NO LONGER REQUIRED TO FILE FORM 990.
FORM 990, PART VI, SECTION A, LINE 6	THE ORGANIZATION MEMBERS CONSIST OF THE 9 BOARD MEMBERS.
FORM 990, PART VI, SECTION A, LINE 7A	SINCE THE ORGANIZATION'S FORMATION, THE GOVERNOR OF MARYLAND HAS APPOINTED THE BOARD OF DIRECTORS WITH THE ADVICE AND CONSENT OF THE STATE SENATE. UNDER LEGISLATION ADOPTED BY THE STATE OF MARYLAND IN 2015, THE ORGANIZATION'S POLICYHOLDERS WERE GRANTED THE RIGHT, PHASED IN FROM 2020 THROUGH 2022, TO APPOINT SEVEN OF THE ORGANIZATION'S NINE DIRECTORS. BEGINNING ON JULY 1ST, 2022, SEVEN OF THE ORGANIZATION'S NINE BOARD MEMBERS HAD BEEN ELECTED BY POLICYHOLDERS. THE POLICYHOLDERS EXERCISING THEIR NEW RIGHT TO APPOINT DIRECTORS MAY NOT RESULT IN ANY EXCHANGE BY THE POLICYHOLDERS FOR U.S. FEDERAL INCOME TAX PURPOSES. THE CONSEQUENCES SHOULD BE THE SAME UNDER EITHER ALTERNATIVE: NO GAIN OR LOSS WILL BE RECOGNIZED BY THE ORGANIZATION OR ITS POLICYHOLDERS AS A RESULT OF THE POLICYHOLDERS EXERCISING THEIR NEW RIGHT TO APPOINT DIRECTORS. ON APRIL 15, 2022, THE IRS ISSUED PRIVATE LETTER RULING("PLR") XXX-XX-XXXX (CONTROL NUMBER PLR 121522-21) STATING THAT THE ORGANIZATION'S STATUS CHANGE WILL NOT BE TREATED AS A SALE OR EXCHANGE, AND ACCORDINGLY, NO GAIN OR LOSS WILL BE REALIZED UNDER SECTION 1001 AS A RESULT OF THE STATUS CHANGE.
FORM 990, PART VI, SECTION A, LINE 7B	A DIRECTOR APPOINTED BY THE GOVERNOR OF MARYLAND MAY BE REMOVED BY THE GOVERNOR FOR INCOMPETENCE OR MISCONDUCT. A DIRECTOR ELECTED BY MEMBERS MAY BE REMOVED BY THE MEMBERS AT ANY TIME, FOR ANY REASON, BY THE AFFIRMATIVE VOTE OF A MAJORITY OF ALL OF THE VOTES ENTITLED TO BE CAST GENERALLY IN THE ELECTION OF DIRECTORS. THE MARYLAND INSURANCE COMMISSIONER MAY REMOVE A DIRECTOR ELECTED BY THE MEMBERS FOR INCOMPETENCE, MISCONDUCT, OR MALFEASANCE AFTER NOTICE AND AN OPPORTUNITY FOR A HEARING AS REQUIRED PURSUANT TO THE INSURANCE CODE.
FORM 990, PART VI, SECTION B, LINE 11B	THE 990 TAX RETURN IS COMPLETED BY AN EXTERNAL ACCOUNTANT AND THE RETURN IS REVIEWED BY MANAGEMENT PRIOR TO FILING THE RETURN.
FORM 990, PART VI, SECTION B, LINE 12C	ALL EMPLOYEES COMPLETE A CONFLICT OF INTEREST QUESTIONNAIRE EACH YEAR. ANY INSTANCES OF POTENTIAL CONFLICT ARE REVIEWED BY HUMAN RESOURCES OR THE CHIEF LEGAL OFFICER FOR THE APPROPRIATE RESOLUTION.
FORM 990, PART VI, SECTION B, LINE 15	COMPENSATION FOR THE CEO, EXECUTIVES, AND TOP MANAGEMENT POSITIONS ARE DETERMINED UPON THE COMPLETION OF AN ANNUAL EVALUATION AND IS BASED UPON INDIVIDUAL AND COMPANY PERFORMANCE AS WELL AS INDUSTRY CONSIDERATIONS AND OTHER BENCHMARK DATA. COMPENSATION FOR THE CEO IS DETERMINED BY THE BOARD OF DIRECTORS AND COMPENSATION FOR OTHER EXECUTIVES AND TOP MANAGEMENT POSITIONS ARE DETERMINED BY THE CEO.
FORM 990, PART VI, SECTION C, LINE 19	THE ORGANIZATION'S GOVERNING DOCUMENTS AND CERTAIN FINANCIAL INFORMATION IS AVAILABLE UPON REQUEST AND CERTAIN FINANCIAL INFORMATION IS AVAILABLE ON THE ORGANIZATION'S WEBSITE.
FORM 990, PART IX, LINE 11G	OTHER FEES FOR SERVICES 15,148,018.
FORM 990, PART XI, LINE 9:	NET ASSETS ADJUSTMENT DUE TO CHANGE IN EXEMPT STATUS -1,098,271,934. CHANGE IN NON ADMITTED ASSETS 1,086,759. BAD DEBT -1,446,990.

For Paperwork Reduction Act Notice, see the Instructions for Form 990 or 990-EZ.

Cat. No. 51056K

Schedule O (Form 990) 2021

Additional Data

Software ID:
Software Version:

- TIN:

SCHEDULE R
(Form 990)

Department of the Treasury
Internal Revenue Service

Related Organizations and Unrelated Partnerships

Complete if the organization answered "Yes" on Form 990, Part IV, line 33, 34, 35b, 36, or 37.
MediumBullet

Attach to Form 990.
MediumBullet

Go to www.irs.gov/Form990 for instructions and the latest information.

OMB No. 1545-0047

2021

Open to Public Inspection

Name of the organization

CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Employer identification number

46-1056754

Part I

Identification of Disregarded Entities. Complete if the organization answered "Yes" on Form 990, Part IV, line 33.

(a) Name, address, and EIN (if applicable) of disregarded entity	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Total income	(e) End-of-year assets	(f) Direct controlling entity
(1) ICUBED VENTURES LLC 8722 LOCH RAVEN BOULEVARD BALTIMORE,MD212862235 83-2289224	INVESTING	MD	53,771	28,307,823	CHESAPEAKE EMPLOYERS' INSURANCE COMPANY

Part II

Identification of Related Tax-Exempt Organizations. Complete if the organization answered "Yes" on Form 990, Part IV, line 34 because it had one or more related tax-exempt organizations during the tax year.

(a) Name, address, and EIN of related organization	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Exempt Code section	(e) Public charity status (if section 501(c)(3))	(f) Direct controlling entity	(g) Section 512(b)(13) controlled entity?
(a) Name, address, and EIN of related organization	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Exempt Code section	(e) Public charity status (if section 501(c)(3))	(f) Direct controlling entity	Yes	No
(1)INJURED WORKERS INSURANCE FUND 8722 LOCH RAVEN BOULEVARD TOWSON,MD212862235 52-2127565	STATE SPONSORED WORKMENS' COMPENSATION INSURANCE	MD	501(C)27				No
(2)STATE OF MARYLAND 100 STATE CIRCLE ANNAPOLIS,MD21401 52-2006962	STATE GOVERNMENT	MD					No

For Paperwork Reduction Act Notice, see the Instructions for Form 990.

Cat. No. 50135Y

Schedule R (Form 990) 2021

Page 2

Part III

Identification of Related Organizations Taxable as a Partnership. Complete if the organization answered "Yes" on Form 990, Part IV, line 34, because it had one or more related organizations treated as a partnership during the tax year.

(a) Name, address, and EIN of related organization	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Direct controlling entity	(f) Share of total income	(g) Share of end-of-year assets	(h) Disproprtionate allocations?		(i) Code V-UBI amount in box 20 of Schedule K-1 (Form 1065)	(j) General or managing partner?		(k) Percentage ownership
(a) Name, address, and EIN of related organization	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Direct controlling entity	(f) Share of total income	(g) Share of end-of-year assets	Yes	No	(i) Code V-UBI amount in box 20 of Schedule K-1 (Form 1065)	Yes	No	(k) Percentage ownership

Part IV

Identification of Related Organizations Taxable as a Corporation or Trust. Complete if the organization answered "Yes" on Form 990, Part IV, line 34 because it had one or more related organizations treated as a corporation or trust during the tax year.

(a) Name, address, and EIN of related organization	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Direct controlling entity	(e) Type of entity (C corp, S corp, or trust)	(f) Share of total income	(g) Share of end-of-year assets	(h) Percentage ownership	(i) Section 512(b)(13) controlled entity?
(a) Name, address, and EIN of related organization	(b) Primary activity	(c) Legal domicile (state or foreign country)	(d) Direct controlling entity	(e) Type of entity (C corp, S corp, or trust)	(f) Share of total income	(g) Share of end-of-year assets	(h) Percentage ownership	Yes	No
(1) CHESAPEAKE RISK SOLUTIONS INC 8722 LOCH RAVEN BOULEVARD TOWSON,MD212862235 83-2306359	THIRD PARTY RISK MANAGEMENT	MD	CHESAPEAKE EMPLOYERS' INSURANCE COMPANY	C			100.000 %	Yes

Schedule R (Form 990) 2021

Page 3

Part V

Transactions With Related Organizations. Complete if the organization answered "Yes" on Form 990, Part IV, line 34, 35b, or 36.

Note. Complete line 1 if any entity is listed in Parts II, III, or IV of this schedule.

Yes

1 During the tax year, did the orgranization engage in any of the following transactions with one or more related organizations listed in Parts II-IV?

a Receipt of (i) interest, (ii) annuities, (iii) royalties, or (iv) rent from a controlled entity .....................

b Gift, grant, or capital contribution to related organization(s) ............................

c Gift, grant, or capital contribution from related organization(s) ............................

d Loans or loan guarantees to or for related organization(s) ............................

Yes

e Loans or loan guarantees by related organization(s) ............................

f Dividends from related organization(s) ............................

g Sale of assets to related organization(s) ............................

h Purchase of assets from related organization(s) ............................

i Exchange of assets with related organization(s) ............................

j Lease of facilities, equipment, or other assets to related organization(s) .......................

k Lease of facilities, equipment, or other assets from related organization(s) ......................

l Performance of services or membership or fundraising solicitations for related organization(s) .....................

m Performance of services or membership or fundraising solicitations by related organization(s) .................

n Sharing of facilities, equipment, mailing lists, or other assets with related organization(s) ...................

Yes

o Sharing of paid employees with related organization(s) ............................

Yes

p Reimbursement paid to related organization(s) for expenses ............................

Yes

q Reimbursement paid by related organization(s) for expenses ............................

Yes

r Other transfer of cash or property to related organization(s) ............................

s Other transfer of cash or property from related organization(s) ............................

Yes

If the answer to any of the above is "Yes," see the instructions for information on who must complete this line, including covered relationships and transaction thresholds.

(a) Name of related organization	(b) Transaction type (a-s)	(c) Amount involved	(d) Method of determining amount involved
(1) INJURED WORKERS INSURANCE FUND	S	6,135,013	FAIR VALUE
(2) INJURED WORKERS INSURANCE FUND	Q	1,678,396	FAIR VALUE
(3) INJURED WORKERS INSURANCE FUND	D	1,281,172	FAIR VALUE

Schedule R (Form 990) 2021

Page 4

Part VI

Unrelated Organizations Taxable as a Partnership. Complete if the organization answered "Yes" on Form 990, Part IV, line 37.

Provide the following information for each entity taxed as a partnership through which the organization conducted more than five percent of its activities (measured by total assets or gross revenue) that was not a related organization. See instructions regarding exclusion for certain investment partnerships.

(a) Name, address, and EIN of entity	(b) Primary activity	(c) Legal domicile (state or foreign country)	(e) Are all partners section 501(c)(3) organizations?		(f) Share of total income	(g) Share of end-of-year assets	(h) Disproprtionate allocations?		(i) Code V-UBI amount in box 20 of Schedule K-1 (Form 1065)	(j) General or managing partner?		(k) Percentage ownership
(a) Name, address, and EIN of entity	(b) Primary activity	(c) Legal domicile (state or foreign country)	Yes	No	(f) Share of total income	(g) Share of end-of-year assets	Yes	No	(i) Code V-UBI amount in box 20 of Schedule K-1 (Form 1065)	Yes	No	(k) Percentage ownership

Schedule R (Form 990) 2021

Page 5

Part VII

Supplemental Information

Provide additional information for responses to questions on Schedule R. See instructions.

Return Reference	Explanation

Schedule R (Form 990) 2021

Additional Data

Software ID:
Software Version: