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 to 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.”
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 their hope 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 that it truly is “A Great Day To Be A Warrior.”
Contributions to this fund help it grow and provide increased awards.