The Timothy Holley, Jr. ’77 Athletic Directorship

Joanna and Jonathon Jacobson ’79 endow a new athletic directorship after longtime friend – and former teammate – Tim Holley ’77.

Tim Holley was a top-notch pitcher and outfielder at Gilman back in the day. Jon Jacobson recalls fondly, however, that his upperclassman teammate did have a penchant for wild pitches. As one of the many who “feared for their lives” at batting practice with Tim on the mound, Jon delights in the oft-told story of a young slugger who was afraid to go up to bat against Tim. “Stand on the plate,” Tim’s catcher is said to have advised. “He’ll never hit you.”

Notwithstanding those wild pitches, Jon regards his close friend as the “poster child for everything Gilman stands for and aspires to be” and as the “prototypical teacher-coach.” His wife Joanna and he are thrilled to honor Tim by establishing an endowed athletic directorship in his name. Tim retired as Gilman’s Athletic Director last year, after ably serving in that role since 1997.

One of the School’s most outstanding student-athletes ever, Tim was captain of the football, basketball, and baseball teams during his senior year and received the William Cabell Bruce Prize for the top student-athlete. He went on to the University of Pennsylvania, where he played baseball for four years and earned a Bachelor’s degree in English under the Navy ROTC Scholarship Program. After serving his country, he returned to Gilman in 1985 to teach English and coach football, basketball, and baseball.

A varsity baseball player for three years and basketball team captain during his senior year, Jon shares Tim’s passion for athletics as an essential element of Gilman’s mind-body-spirit triad. For Jon, athletics embodies Gilman ideals: being a part of a team, learning how to win, and learning how to lose. Lessons learned and relationships forged on the court and field shaped who he is today.  

The Jacobsons’ thoughtful gift coincides aptly with the 50thAnniversary celebration of Gilman’s first black graduates. Jon exudes pride for Tim as one of the courageous, pioneering African-American students who transformed the School with Reddy Finney at the helm. In the same breath, he extols Tim’s parents for their financial sacrifice as Baltimore City School teachers to keep Tim and his younger brother at Gilman.

Co-Athletic Directors Lori Bristow and Russell Wrenn ’96 are the first beneficiaries of the Holley Athletic Directorship. Tim continues his extraordinary service to the School as Director of External Relations, an important new role at Gilman.