Raymond F and Judith K McCaskey 2003

Private foundation · Grantmaker Chicago, IL EIN: 27-6362159

RAYMOND F AND JUDITH K MCCASKEY 2003 is a private foundation based in Chicago, Illinois. Its 2025 filing reports 34 grants totaling $575,000, supporting organizations that include arts and cultural institutions, educational organizations, and community-service nonprofits.

Key facts about Raymond F and Judith K McCaskey 2003

In short: Raymond F and Judith K McCaskey 2003 gave $575K across 34 grants in 2025 (avg $17K), mostly in Illinois. 15% of 2025 grantees were new. Source: 2025 IRS Form 990-PF.

EIN
27-6362159
Latest 990 filing
Form 990-PF, 2025
Annual giving (2025)
$575,000
Grants made (2025)
34
Average grant
$16,912
Median grant
$10,000
New grantees (estimate)
15% first-time grantees (5 of 34, 2025)
Total assets
$6,060,152
Primary geography
Illinois (81% of itemized 2025 grant dollars)
Accepts unsolicited proposals
No
How to apply
The foundation states that it makes contributions only to preselected charitable organizations and does not accept unsolicited requests for funds. Full details ↓

Data from IRS Form 990-PF, 2025; updated September 2026. New grantees are estimated by matching recipient names across years (methodology). Application details from Grantable's research on the foundation's public materials; confirm on its website before applying.

Financial Overview

From 2025 IRS Form 990-PF · View filing

Total Assets

$6.1M

+0.0% YoY

Annual Giving

$575K

+42.9% YoY

Grant Count

34

+17.2% YoY

Avg Grant Size

$17K

+21.8% YoY

Under IRS private-foundation payout rules, Raymond F and Judith K McCaskey 2003 reported a distributable amount of $293K for 2025 — the minimum it must pay out in qualifying distributions.

Is Raymond F and Judith K McCaskey 2003 open to new grantees?

15%

first-time grantees, 2025

In 2025, 5 of 34 grantees (15%) were first-time recipients. First grants averaged $10K; repeat grants $18K. How we count

Medians: $10K first-time, $5K repeat.

  • 71% of 2025 grantees were also funded in 2024. Method
  • Giving grew 25% from 2022 to 2025. Method
  • In 2025 it paid out 198% of its IRS minimum distribution (the 5% rule). Method

Estimate from itemized grant lists in IRS Form 990-PF filings (2020–2025). Recipient names are matched across years, so a renamed or misspelled grantee can look new; grants to individuals are left out. Methodology.

Research compiled by Grantable AI from public sources. Last updated September 2026.

Mission & Focus Areas

No mission statement for the foundation is provided. Its 2025 grants included support for theater and the arts, education and youth programs, humanities, hunger relief, services for people who are blind, and historic preservation.

Grantee missions illustrate the range of supported work. The Lincoln Presidential Foundation says its mission is to make Abraham Lincoln’s life, legacy, and leadership available to all people. Chicago Shakespeare Theater describes its work as creating theatrical experiences for people of all ages and identities. Erikson Institute says it prepares professionals to address challenges facing young children, families, and communities. Chicago Humanities Festival says it promotes public appreciation and understanding of the humanities through festivals and educational programs. Holy Family Ministries says it serves children and adults from underserved Chicago neighborhoods through academic, spiritual, and leadership opportunities. After School Matters says it provides Chicago public high school teens with hands-on programs to develop talents and skills for work and college.

Grantmaking

In filing year 2025, the foundation reported 34 grants totaling $575,000. Grant amounts ranged from $1,000 to $100,000, with a median of $10,000. The largest reported awards were $100,000 each to Chicago Shakespeare Theater for programs to promote theater and the arts and to the Lincoln Presidential Foundation for general support. Other notable grants included $50,000 each to Erikson Institute and Opera House Arts; $25,000 each to Chicago Humanities Festival, Chicago Lighthouse for the Blind, and Holy Family Ministries; and $20,000 each to After School Matters, Chinese American Service League, ELCA World Hunger, Historic Preservation Foundation of the Fortnightly, and United Society of Shakers Sabbathday Lake.

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Geographic Focus

Where this funder awards grants

In 2025, 81% of grant dollars went to recipients in Illinois and 13% to recipients in Maine. Smaller shares went to Ohio (2%), Texas (2%), and New York (1%). The listed Illinois grants include multiple Chicago organizations.

Grant Distribution by State

11states

Share of all 34 itemized 2025 grant dollars.

Cities

ChicagoDeer IsleStoningtonAuburnDeerfieldGalenaHarrisonNew GloucesterNew YorkEnfieldNew LebanonSpringfieldWilliamsburgAugustaChathamSt JohnBlue HillColumbusPorterWinston-Salem

Giving Over Time

Total grant dollars and number of grants per year

$0$200K$400K$600K36 grants202036 grants202134 grants202232 grants202329 grants202434 grants2025

From 2020 to 2025, annual grant giving ranged from $375K (2021) to $575K (2025). In 2025 it made 34 grants totaling $575K.

Grant Insights

How this funder distributes its grants

Top Recipients

Top 10 recipients in 2025

Chicago Shakespeare Theater: $100KChicago Shakespeare Theater$100KLincoln Presidential Foundation: $100KLincoln PresidentialFoundation$100KErikson Institute: $50KErikson Institute$50KOpera House Arts: $50KOpera House Arts$50KChicago Humanities Festival: $25KChicago Humanities Festival$25KChicago Lighthouse for the Blind: $25KChicago Lighthouse for theBlind$25KHoly Family Ministries: $25KHoly Family Ministries$25KAfter School Matters Inc: $20KAfter School Matters Inc$20KChinese American Service League Inc: $20KChinese American ServiceLeague Inc$20KElca World Hunger: $20KElca World Hunger$20K

The largest 2025 recipient was Chicago Shakespeare Theater ($100K). Together the top 10 received $435K.

Grant Size Distribution

165 grants across all recorded years

150<$50K7$50–100K8$100–250K$250–500K$500K–1M$1–5M$5M+

The most common grant size was under $50K: 150 grants of 165 (91%).

Giving History

Grant recipients and amounts by year

RecipientPurposeAmount
Chicago Shakespeare Theater Chicago, ILPrograms to Promote Theater and the Arts$100,000
Lincoln Presidential Foundation Springfield, ILGeneral Support$100,000
Erikson Institute Chicago, ILGeneral Support$50,000
Opera House Arts Chicago, ILGeneral Support$50,000
Chicago Humanities Festival Chicago, ILGeneral Support$25,000
Chicago Lighthouse for the Blind Chicago, ILGeneral Support$25,000
Holy Family Ministries Chicago, ILGeneral Support$25,000
After School Matters Inc Chicago, ILSupport of After School Programs for Children$20,000
Chinese American Service League Inc Chicago, ILGeneral Support$20,000
Elca World Hunger Chicago, ILGeneral Support$20,000

Financial History

Multi-year comparison from IRS filings

Filing year Assets Revenue Expenses Grants
2025 $6,060,152 $641,792 $641,768 $575,000 (34 grants)
2024 $6,060,128 $378,923 $449,820 $402,500 (29 grants)
2023 $6,131,025 $235,574 $438,676 $392,500 (32 grants)
Revenue
Expenses
Qualifying Distributions
Net Investment Income
$0$200K$400K$600K$800K202020212022202320242025
Metric202520242023
Total Assets$6,060,152$6,060,128$6,131,025
Revenue$641,792$378,923$235,574
Expenses$641,768$449,820$438,676
Qualifying Distributions$579,421$406,469$396,032
Net Investment Income$574,634$328,064$185,880
Distributable Amount$292,601$299,681$394,145

Data update history

When this profile's IRS filing data changed on Grantable

  1. Updated Form 990-PF for fiscal year 2020 (received by the IRS May 14, 2021)
  2. Updated Form 990-PF for fiscal year 2021 (received by the IRS May 11, 2022)
  3. Updated Form 990-PF for fiscal year 2022 (received by the IRS May 16, 2023)
  4. Updated Form 990-PF for fiscal year 2023 (received by the IRS May 14, 2024)
  5. Updated Form 990-PF for fiscal year 2024 (received by the IRS May 12, 2025)
  6. Added Form 990-PF for fiscal year 2025 (received by the IRS May 11, 2026)

Leadership & Key People

Leadership team and compensation from IRS filings

The 2025 filing lists Raymond F McCaskey as trustee.

Raymond F and Judith K McCaskey 2003 is led by Raymond F. McCaskey, Trustee on every filing since 2020 — the only officer listed, and uncompensated.

Officers on the 2025 filing

  • Raymond F. McCaskey

    Trustee

    On filings since 2020

    1 hr/week

    No compensation reported

Data from IRS Form 990 filings, 2020–2025. "On filings since" is the earliest filing we hold that lists the person; hours are average hours per week as reported.

Contact

Mailing address: 2450 N Lakeview 6, Chicago, IL 60614
Phone: (773) 525-0183

Frequently asked questions about Raymond F and Judith K McCaskey 2003

How much does Raymond F and Judith K McCaskey 2003 give each year?

Raymond F and Judith K McCaskey 2003 gave $575K across 34 grants in 2025, according to its 2025 IRS Form 990-PF. In 2024 it gave $403K across 29 grants.

What is Raymond F and Judith K McCaskey 2003's typical grant size?

Raymond F and Judith K McCaskey 2003's median grant in 2025 was $10,000, and its average grant was $16,912, across 34 grants on its 2025 IRS Form 990-PF. Organizations receiving their first grant from Raymond F and Judith K McCaskey 2003 that year got $10K on average.

Where does Raymond F and Judith K McCaskey 2003 give grants?

Raymond F and Judith K McCaskey 2003 gives mostly in Illinois: 81% of the grant dollars itemized on its 2025 IRS Form 990-PF went to recipients there. The next largest state was Maine (13%). The most frequent recipient cities were Chicago, IL (13 grants), Deer Isle, ME (6 grants) and Stonington, ME (4 grants).

Does Raymond F and Judith K McCaskey 2003 give general operating support?

Yes: 94% of Raymond F and Judith K McCaskey 2003's 2025 grants with a stated purpose (32 of 34) were for general or operating support, per its 2025 IRS Form 990-PF.

Who are Raymond F and Judith K McCaskey 2003's largest grantees?

Raymond F and Judith K McCaskey 2003's largest 2025 grantees include Chicago Shakespeare Theater ($100,000), Lincoln Presidential Foundation ($100,000) and Erikson Institute ($50,000), according to its 2025 IRS Form 990-PF. Together they received 43% of its itemized 2025 grant dollars.

How large is Raymond F and Judith K McCaskey 2003?

Raymond F and Judith K McCaskey 2003 reported $6.1M in total assets on its 2025 IRS Form 990-PF. It paid out $579K in qualifying distributions that year, against a required minimum of $293K (roughly 5% of its investment assets).

What does Raymond F and Judith K McCaskey 2003 fund?

No mission statement for the foundation is provided. Its 2025 grants included support for theater and the arts, education and youth programs, humanities, hunger relief, services for people who are blind, and historic preservation. See mission & focus areas ↑

How do I apply for a grant from Raymond F and Judith K McCaskey 2003?

The foundation states that it makes contributions only to preselected charitable organizations and does not accept unsolicited requests for funds. Eligibility and process details are in the grantmaking section of this profile. See how to apply ↑

What is Raymond F and Judith K McCaskey 2003's EIN?

Raymond F and Judith K McCaskey 2003's EIN (Employer Identification Number) is 27-6362159. IRS Form 990 filing data is available on this page for 2020–2025.

Does Raymond F and Judith K McCaskey 2003 accept unsolicited proposals?

No, according to Grantable's research on the foundation's published guidelines. See how to apply ↑

Data last updated September 2026. Sourced from IRS Form 990-PF filings. Research dossier generated September 2026.

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