Form990-PF
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Department of the Treasury
Internal Revenue Service

Return of Private Foundation
or Section 4947(a)(1) Trust Treated as Private Foundation
bulletDo not enter social security numbers on this form as it may be made public.
bulletGo to www.irs.gov/Form990PF for instructions and the latest information.
OMB No. 1545-0047
2021
Open to Public Inspection
For calendar year 2021, or tax year beginning 01-01-2021 , and ending 12-31-2021
Name of foundation
MARY MB WAKEFIELD CHARITABLE TRUST
C/O SIPPICAN CAPITAL ADVISORS LLC
Number and street (or P.O. box number if mail is not delivered to street address)125 HIGH STREET 1802
  Room/suite
City or town, state or province, country, and ZIP or foreign postal code
BOSTON, MA02110
A Employer identification number

04-6076048
B Telephone number (see instructions)

(857) 263-8101
C bullet
G Check all that apply:

D 1. Foreign organizations, check here............. bullet
2. Foreign organizations meeting the 85%
test, check here and attach computation ... bullet
E bullet
H Check type of organization:
F bullet
I Fair market value of all assets at end
of year (from Part II, col. (c),
line 16)bullet$37,075,487J Accounting method:
MODIFIED CASH
(Part I, column (d) must be on cash basis.)
Part I Analysis of Revenue and Expenses (The total of amounts in columns (b), (c), and (d) may not necessarily equal the amounts in column (a) (see instructions).) (a) Revenue and
expenses per
books 		(b) Net investment
income 		(c) Adjusted net
income 		(d) Disbursements
for charitable
purposes
(cash basis only)
Revenue 1 Contributions, gifts, grants, etc., received (attach schedule) 123,043
2 Check bullet.............
3 Interest on savings and temporary cash investments      
4 Dividends and interest from securities... 667,677 659,252 667,677
5a Gross rents............      
b Net rental income or (loss)  
6a Net gain or (loss) from sale of assets not on line 10 2,481,263
b Gross sales price for all assets on line 6a 6,904,121
7 Capital gain net income (from Part IV, line 2)... 2,481,263
8 Net short-term capital gain......... 311,530
9 Income modifications...........  
10a Gross sales less returns and allowances  
b Less: Cost of goods sold....  
c Gross profit or (loss) (attach schedule).....    
11 Other income (attach schedule)....... Click to see attachment 7,540 5,141 7,540
12 Total. Add lines 1 through 11........ 3,279,523 3,145,656 986,747
Operating and Administrative Expenses 13 Compensation of officers, directors, trustees, etc. 137,745 0 0 137,745
14 Other employee salaries and wages...... 176,512 0 0 176,512
15 Pension plans, employee benefits....... 43,852 0 0 43,852
16a Legal fees (attach schedule)......... Click to see attachment 2,067 0 0 2,067
b Accounting fees (attach schedule)....... Click to see attachment 10,344 0 0 10,345
c Other professional fees (attach schedule).... Click to see attachment 108,287 101,971 101,971 6,316
17 Interest...............        
18 Taxes (attach schedule) (see instructions)... Click to see attachment 39,706 0 0 39,706
19 Depreciation (attach schedule) and depletion... 101,606 0 0
20 Occupancy.............. 18,514 0 0 18,514
21 Travel, conferences, and meetings....... 603 0 0 603
22 Printing and publications..........        
23 Other expenses (attach schedule)....... Click to see attachment 83,285 0 0 83,285
24 Total operating and administrative expenses.
Add lines 13 through 23.......... 722,521 101,971 101,971 518,945
25 Contributions, gifts, grants paid....... 0 0
26 Total expenses and disbursements. Add lines 24 and 25 722,521 101,971 101,971 518,945
27 Subtract line 26 from line 12:
a Excess of revenue over expenses and disbursements 2,557,002
b Net investment income (if negative, enter -0-) 3,043,685
c Adjusted net income (if negative, enter -0-)... 884,776
For Paperwork Reduction Act Notice, see instructions.
Cat. No. 11289X Form 990-PF (2021)
Form 990-PF (2021)
Page 2
Part II Balance Sheets Attached schedules and amounts in the description column
should be for end-of-year amounts only. (See instructions.) 		Beginning of year End of year
(a) Book Value (b) Book Value (c) Fair Market Value
Assets 1 Cash—non-interest-bearing............. 45,720 22,853 22,853
2 Savings and temporary cash investments.........      
3 Accounts receivable bullet  
Less: allowance for doubtful accounts bullet        
4 Pledges receivable bullet  
Less: allowance for doubtful accounts bullet        
5 Grants receivable.................      
6 Receivables due from officers, directors, trustees, and other
disqualified persons (attach schedule) (see instructions).....      
7 Other notes and loans receivable (attach schedule) bullet  
Less: allowance for doubtful accounts bullet        
8 Inventories for sale or use..............      
9 Prepaid expenses and deferred charges.......... 10,326    
10a Investments—U.S. and state government obligations (attach schedule)      
b Investments—corporate stock (attach schedule)....... 13,108,554 Click to see attachment15,048,061 27,998,475
c Investments—corporate bonds (attach schedule).......      
11 Investments—land, buildings, and equipment: basis bullet  
Less: accumulated depreciation (attach schedule) bullet        
12 Investments—mortgage loans.............      
13 Investments—other (attach schedule).......... 753,892 Click to see attachment1,389,311 1,498,881
14 Land, buildings, and equipment: basis bullet8,798,454
Less: accumulated depreciation (attach schedule) bullet1,256,783 7,594,901 7,541,671 7,541,671
15 Other assets (describe bullet) Click to see attachment12,762 Click to see attachment13,607 Click to see attachment13,607
16 Total assets (to be completed by all filers—see the
instructions. Also, see page 1, item I) 21,526,155 24,015,503 37,075,487
Liabilities 17 Accounts payable and accrued expenses..........   546
18 Grants payable.................    
19 Deferred revenue.................    
20 Loans from officers, directors, trustees, and other disqualified persons    
21 Mortgages and other notes payable (attach schedule)......    
22 Other liabilities (describe bullet) Click to see attachment68,200 Click to see attachment0
23 Total liabilities (add lines 17 through 22)......... 68,200 546
Net Assets or Fund Balances Foundations that follow FASB ASC 958, check here bullet
and complete lines 24, 25, 29 and 30.
24 Net assets without donor restrictions........... 21,454,521 24,010,723
25 Net assets with donor restrictions............ 3,434 4,234
Foundations that do not follow FASB ASC 958, check here bullet
and complete lines 26 through 30.
26 Capital stock, trust principal, or current funds........    
27 Paid-in or capital surplus, or land, bldg., and equipment fund    
28 Retained earnings, accumulated income, endowment, or other funds    
29 Total net assets or fund balances (see instructions)..... 21,457,955 24,014,957
30 Total liabilities and net assets/fund balances (see instructions). 21,526,155 24,015,503
Part III
Analysis of Changes in Net Assets or Fund Balances
1
Total net assets or fund balances at beginning of year—Part II, column (a), line 29 (must agree with end-of-year figure reported on prior year’s return) ...............
1
21,457,955
2
Enter amount from Part I, line 27a .....................
2
2,557,002
3
Other increases not included in line 2 (itemize) bullet
3
0
4
Add lines 1, 2, and 3 ..........................
4
24,014,957
5
Decreases not included in line 2 (itemize) bullet
5
0
6
Total net assets or fund balances at end of year (line 4 minus line 5)—Part II, column (b), line 29 .
6
24,014,957
Form 990-PF (2021)
Form 990-PF (2021)
Page 3
Part IV
Capital Gains and Losses for Tax on Investment Income
(a) List and describe the kind(s) of property sold (e.g., real estate,
2-story brick warehouse; or common stock, 200 shs. MLC Co.)		 (b)
How acquired
P—Purchase
D—Donation 		(c)
Date acquired
(mo., day, yr.) 		(d)
Date sold
(mo., day, yr.)
1 a OPS, LTCG P    
b OPS, STCG P    
c LTCP, LTCG P    
d LTCP, STCG P    
e ENDOWMENT, LTCG P    
ENDOWMENT, STCG P    
CAPITAL GAINS DIVIDENDS P    
(e)
Gross sales price 		(f)
Depreciation allowed
(or allowable) 		(g)
Cost or other basis
plus expense of sale 		(h)
Gain or (loss)
(e) plus (f) minus (g)
a 3,493,600   2,140,043 1,353,557
b 560,906   338,319 222,587
c 1,078,039   693,217 384,822
d 325,011   273,079 51,932
e 1,177,726   761,304 416,422
253,907   216,896 37,011
14,932     14,932
Complete only for assets showing gain in column (h) and owned by the foundation on 12/31/69 (l)
Gains (Col. (h) gain minus
col. (k), but not less than -0-) or
Losses (from col.(h))
(i)
F.M.V. as of 12/31/69 		(j)
Adjusted basis
as of 12/31/69 		(k)
Excess of col. (i)
over col. (j), if any
a       1,353,557
b       222,587
c       384,822
d       51,932
e       416,422
      37,011
      14,932
2 Capital gain net income or (net capital loss) Bracket If gain, also enter in Part I, line 7
If (loss), enter -0- in Part I, line 7		 Bracket 2 2,481,263
3 Net short-term capital gain or (loss) as defined in sections 1222(5) and (6):
If gain, also enter in Part I, line 8, column (c) (see instructions). If (loss), enter -0-
in Part I, line 8 ................... 		Bracket 3 311,530
Form 990-PF (2021)
Form 990-PF (2021)
Page 4
Part V
Excise Tax Based on Investment Income (Section 4940(a), 4940(b), 4940(e), or 4948—see instructions)
1a Exempt operating foundations described in section 4940(d)(2), check here Bullet and enter “N/A" on line 1. Bracket for line 1a
Date of ruling or determination letter:   (attach copy of letter if necessary–see instructions)
b All other domestic foundations enter 1.39% (0.0139) of line 27b. Exempt foreign organizations enter 4% (0.04) of Part I, line 12, col. (b)
2 Tax under section 511 (domestic section 4947(a)(1) trusts and taxable foundations only. Others enter -0-) 2 0
3 Add lines 1 and 2........................... 3 42,307
4 Subtitle A (income) tax (domestic section 4947(a)(1) trusts and taxable foundations only. Others enter -0-) 4 0
5 Tax based on investment income. Subtract line 4 from line 3. If zero or less, enter -0- ..... 5 42,307
6 Credits/Payments:
a 2021 estimated tax payments and 2020 overpayment credited to 2021 6a 5,840
b Exempt foreign organizations—tax withheld at source...... 6b 0
c Tax paid with application for extension of time to file (Form 8868)... 6c 0
d Backup withholding erroneously withheld ........... 6d 0
7 Total credits and payments. Add lines 6a through 6d.............. 7 5,840
8 Enter any penalty for underpayment of estimated tax. Check here if Form 2220 is attached. 8 27
9 Tax due. If the total of lines 5 and 8 is more than line 7, enter amount owed.......Bullet 9 36,494
10 Overpayment. If line 7 is more than the total of lines 5 and 8, enter the amount overpaid...Bullet 10  
11 Enter the amount of line 10 to be: Credited to 2022 estimated taxBullet   RefundedBullet 11  
Part VI-A
Statements Regarding Activities
1a
During the tax year, did the foundation attempt to influence any national, state, or local legislation or did
Yes
No
it participate or intervene in any political campaign? ....................
1a
 
No
b
Did it spend more than $100 during the year (either directly or indirectly) for political purposes? See the instructions
for the definition.................................
1b
 
No
If the answer is "Yes" to 1a or 1b, attach a detailed description of the activities and copies of any materials
published or distributed by the foundation in connection with the activities.
c
Did the foundation file Form 1120-POL for this year?.....................
1c
 
No
d
Enter the amount (if any) of tax on political expenditures (section 4955) imposed during the year:
(1) On the foundation. bullet$ 0(2) On foundation managers.bullet$ 0
e
Enter the reimbursement (if any) paid by the foundation during the year for political expenditure tax imposed
on foundation managers.bullet$ 0
2
Has the foundation engaged in any activities that have not previously been reported to the IRS?.......
2
 
No
If "Yes," attach a detailed description of the activities.
3
Has the foundation made any changes, not previously reported to the IRS, in its governing instrument, articles
of incorporation, or bylaws, or other similar instruments? If "Yes," attach a conformed copy of the changes....
3
 
No
4a
Did the foundation have unrelated business gross income of $1,000 or more during the year?.........
4a
Yes
 
b
If "Yes," has it filed a tax return on Form 990-T for this year?...................
4b
Yes
 
5
Was there a liquidation, termination, dissolution, or substantial contraction during the year?.........
5
 
No
If "Yes," attach the statement required by General Instruction T.
6
Are the requirements of section 508(e) (relating to sections 4941 through 4945) satisfied either:
  • By language in the governing instrument, or
  • By state legislation that effectively amends the governing instrument so that no mandatory directions
    • that conflict with the state law remain in the governing instrument?................
    6
    Yes
     
    7
    Did the foundation have at least $5,000 in assets at any time during the year? If "Yes," complete Part II, col. (c),
    and Part XIV..................................
    7
    Yes
     
    8a
    Enter the states to which the foundation reports or with which it is registered (see instructions)
    bulletMA
    b
    If the answer is "Yes" to line 7, has the foundation furnished a copy of Form 990-PF to the Attorney
    General (or designate) of each state as required by General Instruction G? If "No," attach explanation .
    8b
    Yes
     
    9
    Is the foundation claiming status as a private operating foundation within the meaning of section 4942(j)(3)
    or 4942(j)(5) for calendar year 2021 or the taxable year beginning in 2021? See the instructions for Part XIII.
    If "Yes," complete Part XIII .............................
    9
    Yes
     
    10
    Did any persons become substantial contributors during the tax year? If "Yes," attach a schedule listing their names
    and addresses. ...............................
    10
     
    No
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 5
    Part VI-A
    Statements Regarding Activities (continued)
    11
    At any time during the year, did the foundation, directly or indirectly, own a controlled entity within the
    meaning of section 512(b)(13)? If "Yes," attach schedule. See instructions .............
    11
     
    No
    12
    Did the foundation make a distribution to a donor advised fund over which the foundation or a disqualified person had
    advisory privileges? If "Yes," attach statement. See instructions.................
    12
     
    No
    13
    Did the foundation comply with the public inspection requirements for its annual returns and exemption application?
    13
    Yes
     
    Website addressbulletWAKEFIELDTRUST.ORG
    14
    The books are in care ofbulletGORDON A BARRETT Telephone no.bullet (617) 320-2598

    Located atbullet125 HIGH STREET STE 1802BOSTONMA ZIP+4bullet02110
    15
    Section 4947(a)(1) nonexempt charitable trusts filing Form 990-PF in lieu of Form 1041 —check here .........bullet
    and enter the amount of tax-exempt interest received or accrued during the year ........bullet
    15
     
    16 At any time during calendar year 2021, did the foundation have an interest in or a signature or other authority over YesNo
    a bank, securities, or other financial account in a foreign country? .................
    16   No
    See the instructions for exceptions and filing requirements for FinCEN Form 114. If "Yes", enter the name of the foreign
    country bullet
    Part VI-B
    Statements Regarding Activities for Which Form 4720 May Be Required
    File Form 4720 if any item is checked in the "Yes" column, unless an exception applies.
    Yes
    No
    1a
    During the year did the foundation (either directly or indirectly):
    (1) Engage in the sale or exchange, or leasing of property with a disqualified person? ...........
    1a(1)
     
    No
    (2) Borrow money from, lend money to, or otherwise extend credit to (or accept it from)
    a disqualified person? ..............................
    1a(2)
     
    No
    (3) Furnish goods, services, or facilities to (or accept them from) a disqualified person? ...........
    1a(3)
     
    No
    (4) Pay compensation to, or pay or reimburse the expenses of, a disqualified person? ............
    1a(4)
    Yes
     
    (5) Transfer any income or assets to a disqualified person (or make any of either available
    for the benefit or use of a disqualified person)? ......................
    1a(5)
     
    No
    (6) Agree to pay money or property to a government official? (Exception. Check "No"
    if the foundation agreed to make a grant to or to employ the official for a period
    after termination of government service, if terminating within 90 days.) ...............
    1a(6)
     
    No
    b
    If any answer is "Yes" to 1a(1)–(6), did any of the acts fail to qualify under the exceptions described in Regulations
    section 53.4941(d)-3 or in a current notice regarding disaster assistance? See instructions ..........
    1b
     
    No
    c
    ........bullet
    d
    Did the foundation engage in a prior year in any of the acts described in 1a, other than excepted acts,
    that were not corrected before the first day of the tax year beginning in 2021? .............
    1d
     
    No
    2
    Taxes on failure to distribute income (section 4942) (does not apply for years the foundation was a private
    operating foundation defined in section 4942(j)(3) or 4942(j)(5)):
    a
    At the end of tax year 2021, did the foundation have any undistributed income (lines 6d
    and 6e, Part XII) for tax year(s) beginning before 2021?....................
    2a
     
    No
    If "Yes," list the years bullet20, 20, 20, 20
    b
    Are there any years listed in 2a for which the foundation is not applying the provisions of section 4942(a)(2)
    (relating to incorrect valuation of assets) to the year’s undistributed income? (If applying section 4942(a)(2)
    to all years listed, answer "No" and attach statement—see instructions.) ..............
    2b
     
     
    c
    If the provisions of section 4942(a)(2) are being applied to any of the years listed in 2a, list the years here.
    bullet20, 20, 20, 20
    3a
    Did the foundation hold more than a 2% direct or indirect interest in any business enterprise at
    any time during the year? ..............................
    3a
     
    No
    b
    If "Yes," did it have excess business holdings in 2021 as a result of (1) any purchase by the foundation
    or disqualified persons after May 26, 1969; (2) the lapse of the 5-year period (or longer period approved
    by the Commissioner under section 4943(c)(7)) to dispose of holdings acquired by gift or bequest; or (3)
    the lapse of the 10-, 15-, or 20-year first phase holding period? (Use Schedule C, Form 4720, to determine
    if the foundation had excess business holdings in 2021.) .....................
    3b
     
     
    4a
    Did the foundation invest during the year any amount in a manner that would jeopardize its charitable purposes?
    4a
     
    No
    b
    Did the foundation make any investment in a prior year (but after December 31, 1969) that could jeopardize its
    charitable purpose that had not been removed from jeopardy before the first day of the tax year beginning in 2021? ..
    4b
     
    No
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 6
    Part VI-B
    Statements Regarding Activities for Which Form 4720 May Be Required (continued)
    5a
    During the year did the foundation pay or incur any amount to:
    Yes
    No
    (1) Carry on propaganda, or otherwise attempt to influence legislation (section 4945(e))? ..........
    5a(1)
     
    No
    (2) Influence the outcome of any specific public election (see section 4955); or to carry
    on, directly or indirectly, any voter registration drive? ....................
    5a(2)
     
    No
    (3) Provide a grant to an individual for travel, study, or other similar purposes? .............
    5a(3)
     
    No
    (4) Provide a grant to an organization other than a charitable, etc., organization described
    in section 4945(d)(4)(A)? See instructions ........................
    5a(4)
     
    No
    (5) Provide for any purpose other than religious, charitable, scientific, literary, or
    educational purposes, or for the prevention of cruelty to children or animals? .............
    5a(5)
     
    No
    b
    If any answer is "Yes" to 5a(1)–(5), did any of the transactions fail to qualify under the exceptions described in
    Regulations section 53.4945 or in a current notice regarding disaster assistance? See instructions ........
    5b
     
     
    c
    .........bullet
    d
    If the answer is "Yes" to question 5a(4), does the foundation claim exemption from the
    tax because it maintained expenditure responsibility for the grant? .................
    5d
     
     
    If "Yes," attach the statement required by Regulations section 53.4945–5(d).
    6a
    Did the foundation, during the year, receive any funds, directly or indirectly, to pay premiums on
    a personal benefit contract? .............................
    6a
     
    No
    b
    Did the foundation, during the year, pay premiums, directly or indirectly, on a personal benefit contract? ....
    6b
     
    No
    If "Yes" to 6b, file Form 8870.
    7a
    At any time during the tax year, was the foundation a party to a prohibited tax shelter transaction?
    7a
     
    No
    b
    If "Yes", did the foundation receive any proceeds or have any net income attributable to the transaction? .....
    7b
     
     
    8
    Is the foundation subject to the section 4960 tax on payment(s) of more than $1,000,000 in remuneration or
    excess parachute payment during the year? .........................
    8
     
    No
    Part VII
    Information About Officers, Directors, Trustees, Foundation Managers, Highly Paid Employees,
    and Contractors
    1 List all officers, directors, trustees, foundation managers and their compensation. See instructions
    (a) Name and address (b) Title, and average
    hours per week
    devoted to position     		(c) Compensation
     (If not paid, enter
    -0-)     		(d) Contributions to employee benefit plans and deferred compensation (e) Expense account,
    other allowances
    GORDON C BARRETT TRUSTEE
    4.00     		0 0 0
    125 HIGH STREET STE 1802
    BOSTON,MA02110
    NATHALIE S BINNEY TRUSTEE
    1.00     		0 0 0
    19 CHESTNUT STREET
    SALEM,MA01970
    MARK SMITH EXECUTIVE DIRECTOR
    40.00     		134,003 7,445 0
    1465 BRUSH HILL RD
    MILTON,MA02186
    2 Compensation of five highest-paid employees (other than those included on line 1—see instructions). If none, enter “NONE."
    (a) Name and address of each employee paid more than $50,000 (b) Title, and average
    hours per week
    devoted to position     		(c) Compensation (d) Contributions to
    employee benefit
    plans and deferred
    compensation     		(e) Expense account,
    other allowances
    ERICA MAX EDUC DIR
    40.00     		76,427 4,246 0
    1465 BRUSH HILL RD
    MILTON,MA02186
    DEBORAH MERRIAM GROUNDS SUPER
    40.00     		70,935 3,074 0
    1465 BRUSH HILL RD
    MILTON,MA02186
    ALEXANDER RUSSELL LANDSCAPING DIR
    40.00     		21,150 507 0
    1465 BRUSH HILL RD
    MILTON,MA02186
    Total number of other employees paid over $50,000...................bullet 0
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 7
    Part VII
    Information About Officers, Directors, Trustees, Foundation Managers, Highly Paid Employees,
    and Contractors (continued)
    3 Five highest-paid independent contractors for professional services (see instructions). If none, enter "NONE".
    (a) Name and address of each person paid more than $50,000 (b) Type of service (c) Compensation
    SIPPICAN CAPITAL ADVISORS LLC INVESTMENT MANAGEMENT 101,971
    125 HIGH STREET STE 1802
    BOSTON,MA02110
    Total number of others receiving over $50,000 for professional services.............bullet0
    Part VIII-A
    Summary of Direct Charitable Activities
    List the foundation’s four largest direct charitable activities during the tax year. Include relevant statistical information such as the number of organizations and other beneficiaries served, conferences convened, research papers produced, etc. Expenses
    1 TO SUPPORT LAND CONSERVATION AND HISTORICAL HOUSE PRESERVATION. 339,184
    2 DIRECT & INDIRECT OPERATING AND ADMIN EXPENSES FOR CHARITABLE ACTIVITY 179,761
    3  
    4  
    Part VIII-B
    Summary of Program-Related Investments (see instructions)
    Describe the two largest program-related investments made by the foundation during the tax year on lines 1 and 2. Amount
    1  
    2  
    All other program-related investments. See instructions.
    3  
    Total. Add lines 1 through 3.........................bullet0
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 8
    Part IX
    Minimum Investment Return (All domestic foundations must complete this part. Foreign foundations, see instructions.)
    1
    Fair market value of assets not used (or held for use) directly in carrying out charitable, etc.,
    purposes:
    a
    Average monthly fair market value of securities...................
    1a
    26,094,274
    b
    Average of monthly cash balances.......................
    1b
    690,107
    c
    Fair market value of all other assets (see instructions)................
    1c
    0
    d
    Total (add lines 1a, b, and c).........................
    1d
    26,784,381
    e
    Reduction claimed for blockage or other factors reported on lines 1a and
    1c (attach detailed explanation) .............
    1e
    0
    2
    Acquisition indebtedness applicable to line 1 assets..................
    2
    0
    3
    Subtract line 2 from line 1d.........................
    3
    26,784,381
    4
    Cash deemed held for charitable activities. Enter 1.5% (0.015) of line 3 (for greater amount, see
    instructions) .............................
    4
    401,766
    5
    Net value of noncharitable-use assets. Subtract line 4 from line 3. .......
    5
    26,382,615
    6
    Minimum investment return. Enter 5% (0.05) of line 5................
    6
    1,319,131
    Part X
    Distributable Amount (see instructions) (Section 4942(j)(3) and (j)(5) private operating foundations and certain foreign organizations check here right arrow and do not complete this part.)
    1
    Minimum investment return from Part IX, line 6..................
    1
     
    2a
    Tax on investment income for 2021 from Part V, line 5.......
    2a
     
    b
    Income tax for 2021. (This does not include the tax from Part V.) ...
    2b
     
    c
    Add lines 2a and 2b............................
    2c
     
    3
    Distributable amount before adjustments. Subtract line 2c from line 1............
    3
     
    4
    Recoveries of amounts treated as qualifying distributions................
    4
     
    5
    Add lines 3 and 4............................
    5
     
    6
    Deduction from distributable amount (see instructions).................
    6
     
    7
    Distributable amount as adjusted. Subtract line 6 from line 5. Enter here and on Part XII, line 1 ...
    7
     
    Part XI
    Qualifying Distributions (see instructions)
    1
    Amounts paid (including administrative expenses) to accomplish charitable, etc., purposes:
    a
    Expenses, contributions, gifts, etc.—total from Part I, column (d), line 26 ..........
    1a
     
    b
    Program-related investments—total from Part VIII-B..................
    1b
     
    2
    Amounts paid to acquire assets used (or held for use) directly in carrying out charitable, etc.,
    purposes...............................
    2
     
    3
    Amounts set aside for specific charitable projects that satisfy the:
    a
    Suitability test (prior IRS approval required)....................
    3a
     
    b
    Cash distribution test (attach the required schedule) .................
    3b
     
    4
    Qualifying distributions. Add lines 1a through 3b. Enter here and on Part XII, line 4.
    4
     
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 9
    Part XII
    Undistributed Income (see instructions)
    (a)
    Corpus     		(b)
    Years prior to 2020     		(c)
    2020     		(d)
    2021
    1 Distributable amount for 2021 from Part X, line 7  
    2 Undistributed income, if any, as of the end of 2021:
    a Enter amount for 2020 only.......  
    b Total for prior years:20, 20, 20  
    3 Excess distributions carryover, if any, to 2021:
    a From 2016......  
    b From 2017......  
    c From 2018......  
    d From 2019......  
    e From 2020......  
    f Total of lines 3a through e ........  
    4Qualifying distributions for 2021 from Part
    XI, line 4: bullet$  
    a Applied to 2020, but not more than line 2a  
    b Applied to undistributed income of prior years
    (Election required—see instructions).....     		 
    c Treated as distributions out of corpus (Election
    required—see instructions)........     		 
    d Applied to 2021 distributable amount.....  
    e Remaining amount distributed out of corpus  
    5 Excess distributions carryover applied to 2021.    
    (If an amount appears in column (d), the
    same amount must be shown in column (a).)
    6Enter the net total of each column as
    indicated below:
    a Corpus. Add lines 3f, 4c, and 4e. Subtract line 5  
    b Prior years’ undistributed income. Subtract
    line 4b from line 2b ..........     		 
    c Enter the amount of prior years’ undistributed
    income for which a notice of deficiency has
    been issued, or on which the section 4942(a)
    tax has been previously assessed......     		 
    d Subtract line 6c from line 6b. Taxable amount
    —see instructions ...........     		 
    e Undistributed income for 2019. Subtract line
    4a from line 2a. Taxable amount—see
    instructions .............     		 
    f Undistributed income for 2021. Subtract
    lines 4d and 5 from line 1. This amount must
    be distributed in 2022 ..........     		 
    7 Amounts treated as distributions out of
    corpus to satisfy requirements imposed by
    section 170(b)(1)(F) or 4942(g)(3) (Election may
    be required - see instructions) .......     		 
    8 Excess distributions carryover from 2016 not
    applied on line 5 or line 7 (see instructions) ...     		 
    9 Excess distributions carryover to 2022.
    Subtract lines 7 and 8 from line 6a ......     		 
    10 Analysis of line 9:
    a Excess from 2017....  
    b Excess from 2018....  
    c Excess from 2019....  
    d Excess from 2020....  
    e Excess from 2021....  
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 10
    Part XIII
    Private Operating Foundations (see instructions and Part VI-A, question 9)
    1a If the foundation has received a ruling or determination letter that it is a private operating
    foundation, and the ruling is effective for 2021, enter the date of the ruling ....... bullet
    2005-06-17
    b Check box to indicate whether the organization is a private operating foundation described in section or
    2a Enter the lesser of the adjusted net
    income from Part I or the minimum
    investment return from Part X for each
    year listed ..........     		Tax year Prior 3 years (e) Total
    (a) 2021 (b) 2020 (c) 2019 (d) 2018
    884,776 448,050 356,517 226,334 1,915,677
    b 85% (0.85) of line 2a ......... 752,060 380,843 303,039 192,384 1,628,325
    c Qualifying distributions from Part XI,
    line 4 for each year listed .....     		568,595 558,345 624,395 692,175 2,443,510
    d Amounts included in line 2c not used directly
    for active conduct of exempt activities ..........     		0 0 0 0 0
    e Qualifying distributions made directly
    for active conduct of exempt activities.
    Subtract line 2d from line 2c ....     		568,595 558,345 624,395 692,175 2,443,510
    3 Complete 3a, b, or c for the
    alternative test relied upon:
    a “Assets" alternative test—enter:
    (1) Value of all assets ......         0
    (2) Value of assets qualifying
    under section 4942(j)(3)(B)(i)    		         0
    b “Endowment" alternative test— enter 2/3
    of minimum investment return shown in
    Part IX, line 6 for each year listed ..     		879,421 569,851 620,435 701,021 2,770,728
    c “Support" alternative test—enter:
    (1) Total support other than gross
    investment income (interest,
    dividends, rents, payments
    on securities loans (section
    512(a)(5)), or royalties) ....     		        0
    (2) Support from general public
    and 5 or more exempt
    organizations as provided in
    section 4942(j)(3)(B)(iii)....     		        0
    (3) Largest amount of support
    from an exempt organization    		         0
    (4) Gross investment income         0
    Part XIV
    Supplementary Information (Complete this part only if the foundation had $5,000 or more in
    assets at any time during the year—see instructions.)
    1Information Regarding Foundation Managers:
    aList any managers of the foundation who have contributed more than 2% of the total contributions received by the foundation
    before the close of any tax year (but only if they have contributed more than $5,000). (See section 507(d)(2).)
    bList any managers of the foundation who own 10% or more of the stock of a corporation (or an equally large portion of the
    ownership of a partnership or other entity) of which the foundation has a 10% or greater interest.
    2Information Regarding Contribution, Grant, Gift, Loan, Scholarship, etc., Programs:
    Check here bullet
    aThe name, address, and telephone number or email address of the person to whom applications should be addressed:
    bThe form in which applications should be submitted and information and materials they should include:
    cAny submission deadlines:
    dAny restrictions or limitations on awards, such as by geographical areas, charitable fields, kinds of institutions, or other
    factors:
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 11
    Part XIV
    Supplementary Information (continued)
    3 Grants and Contributions Paid During the Year or Approved for Future Payment
    Recipient If recipient is an individual,
    show any relationship to
    any foundation manager
    or substantial contributor
    		 Foundation
    status of
    recipient     		Purpose of grant or
    contribution     		Amount
    Name and address (home or business)
    aPaid during the year
    Total .................................bullet 3a 0
    bApproved for future payment
    Total .................................bullet 3b 0
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 12
    Part XV-A
    Analysis of Income-Producing Activities
    Enter gross amounts unless otherwise indicated. Unrelated business income Excluded by section 512, 513, or 514 (e)
    Related or exempt
    function income
    (See instructions.)
    1Program service revenue: (a)
    Business code     		(b)
    Amount     		(c)
    Exclusion code     		(d)
    Amount
    a
    b
    c
    d
    e
    f
    gFees and contracts from government agencies          
    2 Membership dues and assessments ....          
    3 Interest on savings and temporary cash
    investments ...........     		         
    4 Dividends and interest from securities ....          
    5 Net rental income or (loss) from real estate:
    aDebt-financed property......          
    bNot debt-financed property.....          
    6 Net rental income or (loss) from personal property          
    7 Other investment income .....          
    8 Gain or (loss) from sales of assets other than
    inventory ............     		    18 2,481,263  
    9 Net income or (loss) from special events:          
    10 Gross profit or (loss) from sales of inventory          
    11 Other revenue:
    aPASS THROUGH INCOME     		  2,399 01 5,141  
    b
    c
    d
    e
    12 Subtotal. Add columns (b), (d), and (e) .. 2,399 3,154,081 0
    13Total. Add line 12, columns (b), (d), and (e)..................
    13
    3,156,480
    (See worksheet in line 13 instructions to verify calculations.)
    Part XV-B
    Relationship of Activities to the Accomplishment of Exempt Purposes
    Line No.
    DownArrow     		Explain below how each activity for which income is reported in column (e) of Part XV-A contributed importantly to
    the accomplishment of the foundation’s exempt purposes (other than by providing funds for such purposes). (See
    instructions.)
    Form 990-PF (2021)
    Form 990-PF (2021)
    Page 13
    Part XVI
    Information Regarding Transfers To and Transactions and Relationships With Noncharitable Exempt Organizations
    1
    Did the organization directly or indirectly engage in any of the following with any other organization described in section 501(c) (other than section 501(c)(3) organizations) or in section 527, relating to political organizations?
    Yes
    No
    a
    Transfers from the reporting foundation to a noncharitable exempt organization of:
    (1) Cash...................................
    1a(1)
     
    No
    (2) Other assets.................................
    1a(2)
     
    No
    b
    Other transactions:
    (1) Sales of assets to a noncharitable exempt organization....................
    1b(1)
     
    No
    (2) Purchases of assets from a noncharitable exempt organization..................
    1b(2)
     
    No
    (3) Rental of facilities, equipment, or other assets.......................
    1b(3)
     
    No
    (4) Reimbursement arrangements...........................
    1b(4)
     
    No
    (5) Loans or loan guarantees.............................
    1b(5)
     
    No
    (6) Performance of services or membership or fundraising solicitations................
    1b(6)
     
    No
    c
    Sharing of facilities, equipment, mailing lists, other assets, or paid employees..............
    1c
     
    No
    d
    If the answer to any of the above is "Yes," complete the following schedule. Column (b) should always show the fair market value
    of the goods, other assets, or services given by the reporting foundation. If the foundation received less than fair market value
    in any transaction or sharing arrangement, show in column (d) the value of the goods, other assets, or services received.
    (a) Line No. (b) Amount involved (c) Name of noncharitable exempt organization (d) Description of transfers, transactions, and sharing arrangements
    2a
    Is the foundation directly or indirectly affiliated with, or related to, one or more tax-exempt organizations
    described in section 501(c) (other than section 501(c)(3)) or in section 527? ...........
    b
    If "Yes," complete the following schedule.

    (a) Name of organization (b) Type of organization (c) Description of relationship
    Sign Here
    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 taxpayer) is based on all information of which preparer has any knowledge.
    Bullet Bullet
    May the IRS discuss this return
    with the preparer shown below?
    See instructions.
    Signature of officer or trustee Date Title
    Paid Preparer Use Only Print/Type preparer's name Preparer's Signature Date PTIN
    Firm's name SmallBullet
    		 Firm's EIN SmallBullet
    Firm's address SmallBullet


    		 Phone no.
    Form 990-PF (2021)
    Additional Data


    Software ID:  
    Software Version:  


    Form 990PF - Special Condition Description:
    Special Condition Description

    TY 2021 AccountingFeesSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Category Amount Net Investment Income Adjusted Net Income Disbursements for Charitable Purposes
    TAX PREP AND BOOKKEEPING FEES 10,344 0 0 10,345

    TY 2021 InvestmentsCorpStockSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Name of Stock End of Year Book Value End of Year Fair Market Value
    EQUITIES 15,048,061 27,998,475

    TY 2021 InvestmentsOtherSchedule2
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Category/ Item Listed at Cost or FMV Book Value End of Year Fair Market Value
    INVESTED CASH AT COST 281,771 281,771
    PARTNERSHIPS AT COST 1,107,540 1,217,110

    TY 2021 LegalFeesSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Category Amount Net Investment Income Adjusted Net Income Disbursements for Charitable Purposes
    LEGAL FEES 2,067 0 0 2,067


    TY 2021 OtherAssetsSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Description Beginning of Year - Book Value End of Year - Book Value End of Year - Fair Market Value
    FED TAX RECEIVABLE 12,762 13,607 13,607


    TY 2021 OtherExpensesSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Description Revenue and Expenses per Books Net Investment Income Adjusted Net Income Disbursements for Charitable Purposes
    MAINTENANCE 16,377 0 0 16,377
    MISCELLANEOUS 4,220 0 0 4,220
    MATERIALS, SMALL TOOLS 3,363 0 0 3,363
    INSURANCE (NON-EMPLOYEE) 21,643 0 0 21,643
    SUPPLIES - GEN'L 4,556 0 0 4,556
    ANIMALS 2,351 0 0 2,351
    STORAGE - RENTING 19,125 0 0 19,125
    WORKERS COMPENSATION 6,028 0 0 6,028
    PROGRAM, EVENT AND FUNDRAISING EXPENSE 5,622 0 0 5,622


    TY 2021 OtherIncomeSchedule2
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Description Revenue And Expenses Per Books Net Investment Income Adjusted Net Income
    PASS THROUGH INCOME 7,540 5,141 7,540


    TY 2021 OtherLiabilitiesSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Description Beginning of Year - Book Value End of Year - Book Value
    SBA PPP LOAN PAYABLE 68,200 0


    TY 2021 OtherProfessionalFeesSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Category Amount Net Investment Income Adjusted Net Income Disbursements for Charitable Purposes
    PAYROLL SERVICES 5,462 0 0 5,462
    INVESTMENT COUNSEL 101,971 101,971 101,971 0
    BANK FEES 854 0 0 854


    TY 2021 ReasonableCauseExplanation
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Explanation:
    THIS IS THE FIRST YEAR IN WHICH THE ORGANIZATION HAS RECEIVED OTHER INVESTMENT INCOME THAT QUALIFIED AS UNRELATED BUSINESS INCOME AND AS A RESULT, THE FORM 990-T WAS NOT EXTENDED. GOING FORWARD THE FORM 990-T AND M-990T WILL BE PROPERLY EXTENDED AND/OR FILED IN A TIMELY MANNER.

    TY 2021 TaxesSchedule
    Name:
    MARY MB WAKEFIELD CHARITABLE TRUST
     
    C/O SIPPICAN CAPITAL ADVISORS LLC
    EIN:
    04-6076048
    Category Amount Net Investment Income Adjusted Net Income Disbursements for Charitable Purposes
    REAL ESTATE - PAYMENTS IN LIEU 10,000 0 0 10,000
    PAYROLL & OTHER 23,945 0 0 23,945
    VEHICLE EXCISE AND OTHER TAXES 5,761 0 0 5,761