The Sidney and Deanna Wolk Family
The Sidney and Deanna Wolk Charitable Foundation is a private foundation established in 2015 and based in Medford, Massachusetts. The foundation was created by Sidney and Deanna Wolk, who built their wealth through the Cross Country Group, one of the largest privately held businesses in Massachusetts. Sidney founded Cross Country Motor Club in 1972, with Deanna's support in the early years.
Financial Overview
From 2024 IRS Form 990-PF · View filing
Total Assets
$35.3M
+67.6% YoY
Annual Giving
$1.5M
-72.8% YoY
Grant Count
14
-53.3% YoY
Avg Grant Size
$105K
-41.7% YoY
Mission & Focus Areas
The foundation provides support across a range of charitable sectors, with particular emphasis on:
- Social services
- Elder care
- Education
- Support for individuals who are blind
- Health care
Grantmaking
The foundation operates on a preselected basis only and does not accept unsolicited applications for funds.
Grant Range
$5,000 to $1,000,000
How to Apply
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Geographic Focus
Where this funder awards grants
The foundation's grantmaking focuses primarily on Massachusetts, with some activity in Florida and Virginia.
Grant Distribution by State
Cities
Financial History
Multi-year comparison from IRS filings
As of December 2024:
- Total assets: $35,261,189
- Total revenues: $15,776,132
- Total expenses: $1,557,906
- Total giving: $1,476,135
As of December 2023:
- Total assets: $21.0 million
- Annual giving: $5,426,449
- Number of grants: 30
- Giving rate: 25.8% of assets
| Metric | 2024 | 2023 | 2022 |
|---|---|---|---|
| Total Assets | $35,261,189 | $21,042,963 | $22,087,706 |
| Revenue | $15,776,132 | $4,587,356 | $363,017 |
| Expenses | $1,557,906 | $5,446,211 | $1,869,135 |
| Qualifying Distributions | $1,484,197 | $5,431,092 | $1,850,400 |
| Net Investment Income | $1,088,989 | $3,144,002 | $435,790 |
| Distributable Amount | $3,208,331 | $2,461,224 | $2,287,601 |
Giving Over Time
Total grant dollars and number of grants per year
Grant Insights
How this funder distributes its grants
Top Recipients
Top 10 recipients in 2024
Grant Size Distribution
102 grants across all recorded years
Giving History
Grant recipients and amounts by year
No grants recorded for .
Leadership & Key People
Leadership team and compensation from IRS filings
Board/Trustees:
- Deanna S. Wolk (Trustee)
- Howard L. Wolk (Trustee)
- Robin A. Wolk (Trustee)
The foundation operates with limited staffing and relies on volunteer board members.
Compensation Overview
From 2024 IRS filing
From 2024 filing
| Name | Title | Hours | Compensation |
|---|---|---|---|
| DEANNA S WOLK | TRUSTEE | 5 | — |
| HOWARD L WOLK | TRUSTEE | 2 | — |
| ROBIN A WOLK | TRUSTEE | 2 | — |
Recent News & Activity
Recent developments and announcements
In January 2021, Sidney and Deanna Wolk announced a $5 million donation to Hebrew SeniorLife to support the organization's Center for Memory Health in Roslindale. The center, which provides Harvard Medical School-affiliated outpatient memory care services for individuals dealing with Alzheimer's disease, dementia, and other cognitive challenges, was renamed the Deanna and Sidney Wolk Center for Memory Health in recognition of their gift.
The Sidney And Deanna Wolk Family - GrantExecDeanna's involvement with Hebrew SeniorLife began through volunteer work, where she taught mahjong to residents and worked in the gift shop. Sidney's commitment to charitable giving was rooted in his family's tradition of tzedakah (charity), where the family contributed spare change to a charity box regardless of financial circumstances.
Wolks donate $5 million for Hebrew SeniorLife\u2019s memory care center\Subject Areas
Focus areas based on grantmaking activity
Data last updated April 2026. Sourced from IRS Form 990-PF filings. Research dossier generated April 2026.
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