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Jack Connors & Robert Keefe Named Foundation Trustees

Jack Connors & Robert Keefe

Jack Connors & Robert Keefe Named Cummings Foundation Trustees celebrates a great American Granting Organization and their newest champions.

BOSTON, March 25, 2022 – Boston philanthropist and advertising mogul Jack Connors, Jr. and WilmerHale senior counsel Robert “Bob” Keefe, Esq. have been appointed to Woburn-based Cummings Foundation’s advisory board. The pair joins 11 other business leaders as community trustees for the $3 billion private foundation.

Connors, a founding partner and former CEO of Hill, Holliday, Connors, Cosmopulos, Inc., has dedicated his retired life to local philanthropy and civic service. He was instrumental in the creation of One Fund Boston, the Campaign for Catholic Schools, Camp Harbor View, and other major community initiatives, and has served on the boards of dozens of corporate, civic, and nonprofit organizations.

Connors’ contributions to Boston’s business and community landscape have repeatedly earned him recognition in Boston Magazine’s “Most Powerful People” and “Most Influential People in Boston Philanthropy.”

Jack Connors & Robert Keefe Named Foundation Trustees

“Jack is a tremendous entrepreneur and philanthropist,” said Bill Cummings, founder of both Cummings Foundation and commercial real estate firm Cummings Properties. “Having partnered with him on past charitable endeavors, we have been so impressed by how naturally and effectively he leverages his business acumen to effect positive change for local community members.”

Keefe graduated with honors from Harvard College and Boston College Law School before ultimately rising to partner as a litigator in WilmerHale’s White-Collar Defense and Investigation Practice. He has stayed on post-retirement as senior counsel at WilmerHale, and serves as a guest lecturer for assorted continuing education programs and corporate compliance courses at local law schools.

A dedicated Cummings Foundation volunteer since 2016, the Winchester resident has played a significant role in both selecting and building relationships with nonprofit grant winners.

“Bob is a sharp legal mind with a heart that’s far bigger than most,” said Cummings. “The Foundation is sure to benefit from his impeccable judgment and thoughtful, committed approach.”

Cummings Foundation has awarded more than $320 million to nonprofits in Middlesex, Essex, and Suffolk counties. Among its 11 other community trustees are the Honorable Margot G. Botsford, retired Massachusetts Supreme Court judge; Dr. Arlan F. Fuller, Jr., retired chief of gynecologic oncology, Massachusetts General Hospital, and VP for oncology services, Winchester Hospital Center for Cancer Care; Dr. Anthony P. Monaco, president of Tufts University; and Richard C. Ockerbloom, retired president of The Boston Globe.


About Cummings Foundation

Woburn-based Cummings Foundation, Inc. was established in 1986 by Joyce and Bill Cummings. The Foundation directly operates its own charitable subsidiaries, including New Horizons retirement communities in Marlborough and Woburn, and Cummings Health Sciences, LLC in North Grafton. Additional information is available at

Alison Harding
[email protected]

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Alison Harding
Alison Harding
Senior Communications/Marketing Specialist at Cummings Properties

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