Highland Street Connection

Highland Street Foundation — formally incorporated as Highland Street Connection — operates as a classic family foundation where the McGrath family drives all funding relationships. Founded in Newton, Massachusetts in 1989 by David J. McGrath Jr. and JoAnn McGrath alongside their five children, the foundation has directed over $260 million to nonprofits across its 35-year history. This history is essential context: this is not a passive grant program but an active community participant with deep Boston-area roots, faith community ties, and personal investments in specific organizations.

The foundational rule for applicants is unambiguous: no unsolicited grant proposals are accepted. Grants emerge from relationships trustees have personally built with nonprofit partners over years, not from open competitive rounds. This means organizational alignment must be demonstrated before the LOI — not in it. The eligibility quiz on the website (highlandstreet.org) is the only formal entry point. It screens for focus-area and geographic fit; if an organization passes, a brief letter of inquiry may then be submitted.

First-time applicants should write a concise, standalone LOI. The foundation explicitly discourages submission of additional materials at this stage. The letter should introduce the organization, articulate the specific funding need, and map it cleanly to one of the six stated priority areas: education, youth programming and mentoring, housing and homelessness prevention, environment, healthcare, or the arts.

The top-50 grantee list reveals organizations appearing across five consecutive grant cycles — Camp Harbor View, Greater Boston Food Bank, YMCA of Greater Boston, Boys & Girls Clubs of Boston, and SquashBusters among them. This pattern signals that Highland Street builds long-term partnerships, not project-to-project relationships. New entrants should plan for a 2-3 year relationship-building horizon before expecting funding.

Geographically, Massachusetts is the overwhelming priority — approximately 85% of grants (1,085 of 1,281 records) go to MA-based organizations. A secondary but consistent California portfolio (116 grants, concentrated in the Palm Springs/Coachella Valley area) reflects trustee connections. Organizations based outside MA and CA face a very high bar.

Key staff: Executive Director Blake Jordan (at least 8 years in role), Senior Director of Programs Noreen McMahon, and Associate Director of Grants & Programs Brian McNulty manage day-to-day grantee relationships. Trustee board — Joann McGrath, David J. McGrath III, Sean P. McGrath, and Michael Keating — holds decision-making authority.

The foundation's grant database contains 1,281 records totaling $20.16 million across multiple years, with a per-grant average of $15,739 and a median of $6,000. This spread reveals a bimodal distribution: many smaller one-time gifts in the $1,000–$10,000 range coexist alongside a core portfolio of substantial multi-year commitments ranging from $25,000 to $250,000+ annually.

Annual total giving has ranged from $6.81M (FY2021) to $7.93M (FY2023) in recent years. FY2019 shows an anomalous $38.7M in giving — almost certainly a one-time strategic distribution — after which giving normalized to $7–8M. With assets now at $60.4M (FY2024 preliminary) and net investment income of $4.76M in FY2023, the foundation can sustain but not meaningfully grow its current giving level without asset appreciation.

A critical distinction: total giving is not equivalent to grants paid to external organizations. The foundation funds direct community programming alongside its grantmaking. In FY2023, grants paid to external organizations were $3.96M against total giving of $7.93M — roughly a 50/50 split. In FY2022, grants paid were $3.92M vs. $7.43M total giving. Organizations seeking external grants are therefore competing for approximately $4M/year in outgoing grant dollars, not $8M.

By focus area, the grantee database suggests: Education (~35% of grant dollars, anchored by Catholic and independent school partnerships including Boston College, Cathedral High School, Nativity schools, and the Catholic Schools Foundation), Youth programming and mentoring (~20%, led by Camp Harbor View, Boys & Girls Clubs, Let's Get Ready, and SquashBusters), Community services (~20%, including Greater Boston Food Bank, Saint Francis House, and English for New Bostonians), Healthcare (~12%, split between Boston-area clinical programs and the California-based Eisenhower Health Foundation), and Arts & culture (~13%, including the Boston Symphony Orchestra, Museum of Fine Arts, and Palm Springs-area institutions).

Geographic breakdown: Massachusetts 85% (1,085 grants), California 9% (116 grants), Maine 2% (28 grants), and DC/NY/TN/FL/WI/WY combined 4%.

Grant size scales sharply with relationship maturity. Top grantee Mentor/National Mentoring Partnership received $677,500 across five cycles (~$135,500/year); Boston College and Eisenhower Health Foundation each received $610,000–$615,000 over five years. First-cycle or newer grantees should anchor initial requests in the $15,000–$50,000 range.

The table below compares Highland Street Foundation to four comparable Massachusetts-area foundations based on publicly available 990 data and foundation profiles (figures approximate).

Highland Street Foundation is smaller in assets than most Boston-area peers but comparably active in grantmaking relative to its size — distributing roughly 13% of assets annually in total giving. Its relationship-only model aligns it with Barr and Cabot Family rather than Boston Foundation or Cummings, both of which accept open applications. What distinguishes Highland Street is its dual mandate across six focus areas simultaneously, whereas larger peers tend to specialize (Barr narrowly emphasizes climate/arts/learning; Cabot emphasizes arts and social services). Grant seekers who have been rejected or passed over by invitation-only peers should note that Highland Street's combination of six focus areas, Catholic education affinity, and dual MA/CA geography creates a somewhat wider eligibility window than most invitation-only foundations of comparable size.

No major leadership changes, new program announcements, or notable single grants from 2025–2026 were surfaced in open web sources — consistent with the foundation's deliberately low public profile.

The most recent confirmed financial data is the FY2023 Form 990 (published on ProPublica in November 2025), showing assets of $66.8M and total giving of $7.93M. Preliminary FY2024 data shows assets of $60.4M and revenue of $6.7M, suggesting continued asset decline. The five-year asset trajectory — $75.9M (2021), $72.7M (2022), $66.8M (2023), $60.4M (2024) — represents a roughly $15M reduction over four years, driven by distributions exceeding investment returns.

Signature programs remain fully active as of the foundation's current website: TADpole 10 (free summer family programming), August Adventures (arts/cultural access for underserved youth), Winter Camp (February vacation activities), and Spring Week. The JoAnn McGrath Women's Empowerment initiative and Let's Get Rolling (youth bike-riding) are also listed as ongoing.

Executive Director Blake Jordan has led the foundation for at least eight years, with compensation rising from $413,979 (FY2020) to $465,895 (FY2023), reflecting institutional stability. Trustee composition — Joann McGrath, David J. McGrath III, Sean P. McGrath, and Michael Keating — appears stable across all available 990 filings.

For the most current program news, the foundation's LinkedIn (linkedin.com/company/highland-street-foundation) and The Connection Newsletter (highlandstreet.org/connection-newsletter) are the primary channels. Grant seekers should monitor both for announcements of new initiatives or focus-area shifts.

Applying to Highland Street Foundation requires a fundamentally different posture than competing for open grant programs. The process is designed to confirm fit, not to rank proposals. Here is what sophisticated applicants need to know:

Complete the eligibility quiz first, without exception. The foundation routes all initial contact through its online eligibility quiz (highlandstreet.org/grants). Attempting to bypass this with a cold call or email to staff is likely to produce a referral back to the quiz — and signals that your organization doesn't follow instructions.

Your LOI is a door-opener, not a full proposal. Keep it to 1–2 pages maximum. Include: a one-paragraph organizational overview, the specific program or need requiring support, your requested dollar amount, and how the work serves children and families in Massachusetts or California. Do not attach annual reports, budgets, or program evaluations unless the foundation explicitly requests them.

Make one ask per inquiry. If your organization works across multiple areas (e.g., education and healthcare), choose the single strongest alignment and submit one request. Multi-program LOIs read as unfocused and reduce approval likelihood.

Frame everything through the children-and-families lens. The stated mission is addressing pressing needs for children and families in Massachusetts and California. Even if primary beneficiaries are adults, articulate the downstream family impact explicitly.

Use faith-aligned framing if applicable. The grantee portfolio features multiple Catholic institutions — Cathedral High School, Sacred Heart Church and Catholic School, Nativity Preparatory School of New Bedford, Nativity School of Worcester, and Catholic Schools Foundation — suggesting trustees have strong personal connections to faith-based education. Organizations in this space may find a faster path to consideration.

Time your submission for January–March or September–November. With no set deadlines and a 12-week review cycle, avoid December and August when foundation staff are occupied with holiday programming and summer initiatives.

Start modest on your first ask. Given a median grant of $6,000 and first-cycle relationship norms, anchor an initial request in the $15,000–$35,000 range. Demonstrate impact, deliver on reporting, and scale requests in subsequent cycles.

Build relationships at foundation events. August Adventures, TADpole events, and other public programs create organic touchpoints where nonprofit staff can engage foundation personnel informally. These encounters, over time, are how most funded relationships begin.