Raymond F and Judith K Mccaskey 2003

CHICAGO, IL EIN: 27-6362159

The Raymond F and Judith K McCaskey 2003 Charitable Trust is a private family foundation based in Chicago, Illinois. Founded by Raymond F. McCaskey and Judith K. McCaskey, the trust operates as a 501(c)(3) organization dedicated to philanthropic giving across multiple sectors.

Financial Overview

From 2024 IRS Form 990-PF · View filing

Total Assets

$6.1M

-1.2% YoY

Annual Giving

$403K

+2.5% YoY

Grant Count

29

-9.4% YoY

Avg Grant Size

$14K

+13.2% YoY

Under IRS private-foundation payout rules, Raymond F and Judith K Mccaskey 2003 reported a distributable amount of $300K for 2024 — the minimum it must pay out in qualifying distributions.

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

Mission & Focus Areas

The trust primarily funds:

  • Religious education for families and youth
  • After-school programs for children
  • Theater and the arts
  • General support for select organizations

The foundation has demonstrated particular commitment to arts and cultural institutions, as well as educational and youth-focused initiatives.

Grantmaking

The foundation made an additional 24 grants totaling $380,500 in the same period.

Grant Range

$500–$100,000

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Geographic Focus

Where this funder awards grants

The trust primarily funds organizations in Illinois, Maine, and New York, with a notable concentration of activity in the Chicago area.

Grant Distribution by State

10states
+3 more states

Cities

AuburnAugustaChathamChicagoDeer IsleDeerfieldEnfieldGalenaHarrisonNew GloucesterNew LebanonNew YorkSpringfieldSt JohnStoningtonWilliamsburgWinstonsalem

Financial History

Multi-year comparison from IRS filings

As of 2024:

  • Total assets: $6,060,128
  • Total giving: $402,500
  • Total revenues: $378,923
  • Total expenses: $449,820
  • Number of employees: 0
Revenue
Expenses
Qualifying Distributions
Net Investment Income
$0$196K$392K$588K$784K20202021202220232024
Metric202420232022
Total Assets$6,060,128$6,131,025$6,334,127
Revenue$378,923$235,574$-96,832
Expenses$449,820$438,676$518,742
Qualifying Distributions$406,469$396,032$474,144
Net Investment Income$328,064$185,880$88,996
Distributable Amount$299,681$394,145$404,775

Giving Over Time

Total grant dollars and number of grants per year

$0$115K$230K$345K$461K36 grants202036 grants202134 grants202232 grants202329 grants2024

Grant Insights

How this funder distributes its grants

Top Recipients

Top 10 recipients in 2024

CHICAGO SHAKESPEARE THEA…$100KLINCOLN PRESIDENTIAL FOU…$100KCHICAGO HUMANITIES FESTI…$25KTHE CHICAGO LIGHTHOUSE F…$25KEVANGELICAL LUTHERAN CHU…$20KUNITED SOCIETY OF SHAKER…$20KAFTER SCHOOL MATTERS INC$15KHISTORIC PRESERVATION FO…$15KCHINESE AMERICAN SERVICE…$10KCITY WITH DWELLINGS COMM…$10K

Grant Size Distribution

167 grants across all recorded years

153<$50K7$50–100K7$100–250K$250–500K$500K–1M$1–5M$5M+

Giving History

Grant recipients and amounts by year

Among its reported 2024 grants, the largest include Chicago Shakespeare Theater ($100,000), Lincoln Presidential Foundation ($100,000), Chicago Humanities Festival ($25,000).

RecipientPurposeAmount
AFTER SCHOOL MATTERS INC CHICAGO, ILSUPPORT OF AFTER SCHOOL PROGRAMS FOR CHILDREN$15,000
AMERICAN FOLK ART MUSEUM NEW YORK, NYGENERAL SUPPORT$2,500
CHICAGO HUMANITIES FESTIVAL CHICAGO, ILGENERAL SUPPORT$25,000
CHICAGO SHAKESPEARE THEATER CHICAGO, ILPROGRAMS TO PROMOTE THEATER AND THE ARTS$100,000
CHINESE AMERICAN SERVICE LEAGUE INC CHICAGO, ILGENERAL SUPPORT$10,000
CHOSEN VALE INC (DBA ENFIELD SHAKER MUSEUM) ENFIELD, NHGENERAL SUPPORT$2,000
CITY WITH DWELLINGS COMMUNITY FIRST INITIATIVE WINSTONSALEM, NCGENERAL SUPPORT$10,000
DEER ISLE STONINGTON HISTORICAL SOCIETY DEER ISLE, MEGENERAL SUPPORT$1,000
EVANGELICAL LUTHERAN CHURCH IN AMERICA CHICAGO, ILGENERAL SUPPORT$20,000
FRIENDS OF HISTORIC SECOND CHURCH CHICAGO, ILGENERAL SUPPORT$2,000

Leadership & Key People

Leadership team and compensation from IRS filings

Raymond F. McCaskey and Judith K. McCaskey are the founders of the trust. Both have been recognized as philanthropists contributing to Chicago's charitable landscape.

Compensation Overview

From 2024 IRS filing

From 2024 filing

NameTitleHoursCompensation
RAYMOND F MCCASKEYTRUSTEE1

Contact Information

Address: 2450 N Lakeview Ave, Unit 6 Chicago, IL 60614-2878

Telephone: 773-525-0183

EIN: 27-6362159

Frequently Asked Questions

What does Raymond F and Judith K Mccaskey 2003 fund?

The trust primarily funds: • Religious education for families and youth • After-school programs for children • Theater and the arts • General support for select organizations The foundation has demonstrated particular commitment to arts and cultural institutions, as well as educational and youth-focused initiatives.

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

**Grant Activity:** • Made 34 grants in the most recent reporting year • Total giving: $402,500 • Typical grant range: $500–$100,000 **Recent Grants (2024):** • Lincoln Presidential Foundation: $100,000 (General Support) • Chicago Shakespeare Theater: $100,000 (Programs to Promote Theater and the Arts) • The Chicago Lighthouse for People Who Are Blind or Visually Impaired: $25,000 (General Support) The foundation made an additional 24 grants totaling $380,500 in the same period.

Where does Raymond F and Judith K Mccaskey 2003 make grants?

The trust primarily funds organizations in Illinois, Maine, and New York, with a notable concentration of activity in the Chicago area.

What size grants does Raymond F and Judith K Mccaskey 2003 award?

In 2024, Raymond F and Judith K Mccaskey 2003 awarded 29 grants totaling $403K — an average of about $14K per grant, based on its IRS Form 990 filings.

How much is Raymond F and Judith K Mccaskey 2003 required to give away each year?

Private foundations must generally distribute about 5% of their assets annually. For 2024, Raymond F and Judith K Mccaskey 2003 reported a distributable amount of $300K on its IRS Form 990-PF — the minimum it must pay out in qualifying distributions.

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 2020–2024.

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

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