Tillery Family Foundation

## Approach Strategy

The Tillery Family Foundation operates as a tightly focused family scholarship fund honoring the legacy of Calvin C. Tillery Sr., a community figure who championed education and passed away at age 92. The foundation's philanthropic model is relationship-driven and community-rooted, centering on South Side Chicago high schools rather than a broad open application process.

Primary Strategy: Demonstrate South Side Chicago Roots The foundation's geographic filter is non-negotiable. All known recipients have attended schools concentrated in the South Shore, Woodlawn, and Englewood corridors — South Shore International College Prep, Leo Catholic High School, Gwendolyn Brooks College Prep, Hyde Park Academy, and Homewood-Flossmoor. Any applicant without a genuine South Side Chicago connection should not apply.

Secondary Strategy: Embody the Tillery Values Calvin Tillery Sr.'s stated philosophy was "Use your head for more than a hat rack" — meaning intellectual ambition combined with practical work ethic. Applications should reflect both: strong academic performance AND demonstrated initiative, employment, internships, or community service. Pure GPA is not enough; past winners have included a student who interned with the Chicago Transit Authority (business/marketing) and a HOSA delegate pursuing healthcare.

Recommended Pathways - Healthcare and medical careers (CRNA, nursing, pre-med) are strongly represented in the known recipient pool. - First-generation college students are explicitly celebrated (Leo Catholic winner Kshawn was noted as "the first in his family to earn a high school diploma"). - Students who intend to return to and serve Chicago communities are prioritized — one recipient quoted her goal as "return to the underserved and overlooked areas of Chicago." - Liberal arts applicants (theater + psychology at Pomona College) have won, showing breadth beyond STEM.

Contact Approach The foundation is small (no staff listed; family-run) and communicates via tilleryfoundation@gmail.com. Direct, respectful outreach by email is the appropriate first contact. The foundation's website mentions donations help "increase the scholarship award amount," indicating the fund size is actively being grown.

## Funding Patterns

Asset Base and Scale The Tillery Family Foundation held $2,009,112 in assets as of the most recent IRS 990-PF filing, with $463,698 in annual income (investment returns and donations). This places it in the small-to-mid tier of family scholarship foundations nationally. At a typical payout rate of 5–7% of assets, annual grantmaking likely falls in the $100,000–$140,000 range, though actual scholarship amounts per student are modest (estimated $500–$2,000 per award based on the asset size and number of annual recipients).

Annual Cycle The foundation awards scholarships annually, coinciding with the spring high school graduation season. The 2025 recipient cohort and 2024 recipient cohort are both listed on the website, confirming a consistent year-over-year award cycle. Recipients are typically announced mid-to-late spring.

Number of Awards Based on website listings, the foundation awards approximately 4–6 scholarships per year — drawn from multiple Chicago high schools. This is not a single-winner competition; multiple students are recognized each cycle.

Income Stability With $463,698 in annual income against $2,009,112 in assets, the foundation generates approximately a 23% annual yield relative to assets, which suggests a combination of investment income and active donor contributions. The website solicits monetary donations specifically to "increase the scholarship award amount," indicating the fund is actively fundraising alongside its endowment.

Geographic Concentration (Illinois Only) Despite being incorporated in Delaware (common for tax/legal reasons), all known grantees are from Illinois, specifically the South Side of Chicago. The prior database record incorrectly listed geographic focus as CA and TX; this has been corrected to IL.

No Evidence of Institutional Grantmaking The foundation does not appear to make grants to nonprofit organizations. All funding flows directly to individual students as scholarships. This is not a foundation that funds programs, projects, or 501(c)(3) organizations.

## Peer Comparison

The following table compares the Tillery Family Foundation to similar small family scholarship foundations serving underrepresented student populations in the Midwest.

Key Takeaways from Peer Analysis - At $2.0M in assets, the Tillery Foundation sits at the lower end of this peer group but is well within range of foundations that sustain 4–8 scholarships per year. - The income-to-assets ratio (23%) is the highest in the peer group, suggesting active donor contributions supplement investment returns — a sign of strong community engagement. - The Tillery Foundation is distinctively urban and community-specific, unlike most peers which serve rural or suburban areas. This community specificity is a strength for applicants who authentically belong to the South Side Chicago community. - The foundation's dual program approach (scholarships + Winter Coat Drive) differentiates it from pure scholarship trusts — it maintains active community engagement beyond financial awards.

## Recent Activity

2025 Scholarship Recipients (confirmed) - Student from South Shore International College Prep — enrolled at University of Wisconsin–Madison, pursuing healthcare/CRNA track; HOSA delegate 2023–2024; track athlete - Student from Leo Catholic High School (Kshawn) — first-generation high school graduate; former CTA summer intern; pursuing business/marketing - Student from Gwendolyn Brooks College Prep (Deja) — enrolled at University of Illinois–Urbana/Champaign; earned an Associate's degree while still in high school at age 18; first-generation college student - Kennedy Marina Perkins (great-granddaughter of Calvin Tillery Sr.) — enrolled at Spelman College, Psychology/pre-med track

2024 Scholarship Recipients (confirmed) - Student from Homewood-Flossmoor High School (Matthew) — Tennessee State University, Business Administration/Entrepreneurship; NSBE junior member - Student from South Shore International College Prep (Kate) — Pomona College, Theater and Psychology; interest in healthcare

Winter Coat Drive (ongoing) The foundation runs a winter coat drive collecting new or lightly used coats, hats, and gloves. Drop-off locations are Tabor Christian Church (7950 S. Escanaba Ave, Chicago) and First Baptist Church of Chicago. The drive is held annually and complements the scholarship program.

Website Activity The foundation's website (tilleryfamilyfoundation.org) is actively maintained on GoDaddy's website builder. The copyright reads 2026, confirming current upkeep. The site actively solicits both in-kind donations (coats) and monetary contributions to grow the scholarship fund.

Foundation Trajectory The foundation appears to be expanding its scholarship cohort year over year — the 2025 class appears larger than 2024, including the notable addition of Calvin Tillery Sr.'s own great-granddaughter as a recipient. This suggests the family is deepening its commitment as assets grow.

## Application Tips

1. Lead with Your South Side Chicago Story The single most important criterion is authenticity to the community. Do not apply if you are not from the South Side. For those who are, open with your specific neighborhood, school, and community ties. Mention streets, schools, churches, and local organizations by name. The foundation knows South Side Chicago intimately.

2. Name Calvin C. Tillery Sr. and His Values Show you understand who you are applying in honor of. Reference his philosophy — work ethic, education, and giving back. Frame your accomplishments in those terms. Saying "I embody Calvin Tillery's belief that you should use your head for more than a hat rack" is not just flattery; it shows you did your research.

3. Showcase First-Generation and Work-Ethic Credentials Being first-generation is explicitly celebrated by this foundation. If you are the first in your family to attend college, say so prominently. If you have worked, held an internship, or balanced work and school, describe it concretely (employer, duties, what you learned).

4. Tie Your Career Back to Chicago Multiple past winners explicitly stated intentions to return to underserved Chicago communities in their careers. If this reflects your authentic goals, articulate it — healthcare disparities in Bronzeville, teaching in Englewood, legal services in South Shore. Make it specific and genuine.

5. Apply Early and Communicate Directly As a family-run foundation, the Tillery Foundation responds to direct, respectful email outreach. Write to tilleryfoundation@gmail.com to ask about the current application cycle, deadlines, and any materials required. Keep the email brief, warm, and professional. Avoid form-letter language.

6. Highlight Community Service and Extracurriculars The award is explicitly for "well-rounded" students, not just high academic achievers. HOSA memberships, NSBE chapters, student government, athletics, and volunteer work all appear in past recipient bios. Lead with your full profile, not only your GPA.

7. Consider Supporting the Foundation's Coat Drive Participating in (or organizing a collection for) the Winter Coat Drive before applying demonstrates genuine community alignment, not just scholarship interest. Mention it if relevant.

Likely Disqualifiers - Not living on the South Side of Chicago - Application focused purely on academic metrics without community engagement - No connection to the schools the foundation serves - Generic scholarship application language with no specificity to Tillery's mission