Dennis and Lois O'Leary Scholarship Fund Established at TSF of Wakefield

(Wakefield, MA) – The Scholarship Foundation of Wakefield, Inc. (TSF) is honored to announce the establishment of the Dennis and Lois O’Leary Fund. Beginning in June 2026, a scholarship will be awarded from this fund to a Wakefield student pursuing education after high school.

Dennis O’Leary served as an educator in the Wakefield Public Schools for 32 years. From 1995 until his retirement in 2016, he held the position of Assistant Principal at Wakefield Memorial High School. To the high school community, Dennis O’Leary’s name is synonymous with the phrases “It’s A Great Day To Be A Warrior” and “Fill In Your Dash.”

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Dennis and Lois have shared a life together dedicated to “filling in their dash” - the meaningful space between dates where true legacy is built. Together, they live by a simple but powerful philosophy: that life is meant to be lived to the fullest while taking a genuine interest in the stories of others and making a meaningful impact. This fund is an extension of their daily practice: investing in people, fostering connection, and ensuring that the next generation has the support to make their own “dash” just as vibrant and purposeful.

It is the hope of Dennis and Lois that the recipient of this award will be empowered to seek to live fully with unwavering optimism, to lead with kindness and to prove every day is truly “A Great Day To Be A Warrior.”

Donations to the Dennis and Lois O’Leary Fund can be made to TSF of Wakefield, P.O. Box 321, Wakefield, MA 01880. Online donations can be made by visiting www.TSFofWakefield.org/donate. Please include the name of the fund with your donation, either on the check memo line or by adding a message/fund name with your online donation. Venmo payments can be made by searching for the charity @TSFofWakefieldMA.

Founded in 1960, The Scholarship Foundation of Wakefield is dedicated to providing financial assistance to Wakefield residents pursuing full-time higher education. In addition to supporting students, TSF administers over 635 scholarship funds established by community members to honor individuals, families, businesses, and organizations. For more information, including a complete list of funds, visit TSFofWakefield.org or call 781-245-4890.