Timothy Holley, Jr. ’77 first returned to his alma mater from 1985–1994 when he was an Upper School English teacher and coached football, basketball, and baseball, including a successful stint as varsity basketball head coach. He was named the Baltimore Sun B Conference Coach of the Year in 1990.

After serving for three years as Director of Athletics at The Haverford School outside of Philadelphia, Pennsylvania, from 1994–1997, he returned to Gilman in 1997 as Director of Athletics at Gilman, a role he served through 2018. 

After going on sabbatical in the spring of 2018, Holley, once again, returned to Gilman in a new position as Director of External Relations in the Development Office in the summer of 2018. In the fall of 2023, Holley went back to full-time teaching and coaching as an English teacher in the Upper School.

Over his 38 years on the Gilman faculty, Holley became the only person in school history to have served as Director of Athletics, Head Varsity Football Coach, Head Varsity Basketball Coach, and Head Varsity Baseball Coach during his career.

Holley was certified by the National Interscholastic Athletic Administrators Association (NIAAA) as a Certified Athletic Administrator (CAA) in 2016. He was named the Maryland State Athletic Director’s Association (MSADA) MIAA Schools Athletic Director of the Year in 2003 and 2016. 

As a Gilman faculty member, he has been awarded the Dunn Fellowship, the Broadus-Hubbard Award, the Russell Chair, the Thomas Chair, the Reipe Sabbatical, and the May Holmes Service Award. In 2019, the position of Director of Athletics at Gilman was endowed in his name.

Prior to his teaching and coaching career, Holley was commissioned in 1981 as an active duty officer in the United States Navy. He earned Commendation and Service medals for his efforts with the Multinational Peacekeeping Force in Beirut, Lebanon. He later served for nine years in the U.S. Navy Reserve, attaining the rank of Lieutenant Commander in 1991.

Holley graduated in 1981 from the University of Pennsylvania with a bachelor’s in English. There, he played freshman football, was a four-year member of the varsity baseball team, and graduated from the Naval Reserve Officers Training Corps (NROTC) program.

Holley earned the William Cabell Bruce Prize as Gilman’s top student-athlete in 1977. He captained the football, basketball, and baseball teams during his senior year. He was Maryland’s leading football rusher in 1976, earning first-team all-state honors and Player of the Year awards. Also, he twice won the Alumni Baseball Cup as the Gilman baseball team’s top player.