A MIAA legend announces his retirement

Few individuals have left a larger imprint on Gilman School athletics and the MIAA than Timothy Holley Jr.

A member of Gilman's Class of 1977 and a standout multi-sport athlete with the Greyhounds, Holley has spent nearly four decades as a teacher, coach, administrator and mentor at his alma mater, establishing a legacy unmatched in school history. Holley, who has announced his retirement, effective at the end of the 2025-26 school year, also was an instrumental figure in MIAA leadership

Holley's journey as an educator and coach began at Gilman in 1985 when he returned as an Upper School English teacher. Over the next nine years, he coached football, basketball and baseball. During this time, the Greyhounds' varsity basketball program enjoyed considerable success and he was recognized as the Baltimore Sun's B Conference Coach of the Year in 1990.

Holley left Gilman from 1994 to 1997 to serve as Director of Athletics at The Haverford School, but returned to Gilman, where he would spend the next 21 years overseeing one of Maryland's premier athletic programs as Director of Athletics.

His contributions to interscholastic athletics have been recognized well beyond Gilman's campus. Holley earned Certified Athletic Administrator status from the National Interscholastic Athletic Administrators Association (NIAAA) in 2016 and was twice named the Maryland State Athletic Directors Association (MSADA) choice as MIAA Athletic Director of the Year, receiving the honor in 2003 and 2016.

Throughout his tenure as athletic director, Holley was also an influential figure within the MIAA, serving on the Association’s Executive Committee for seven years spending two year’s as its president between 2015-16. In addition, he chaired numerous sports committees.

“Tim has served the MIAA in many capacities over the years,” said MIAA Executive Director Paul Bernstorf. “He has been through the leadership circuit of the MIAA, going from sport chairperson to 2nd VP to VP to President of the MIAA. He is always eloquent in expressing himself and always put the student’s best interests first. Each of us is better because of our relationship with Coach Holley. I am honored to be able to call Tim Holley my friend.”

His leadership helped strengthen Gilman's reputation as one of the nation's elite independent school athletic programs while mentoring generations of coaches and student-athletes. In 2019, the school permanently honored his contributions by endowing the Director of Athletics position in his name.

“Early in his student days, Timmy had all the characteristics that so clearly define him now as a Gilman man,” said Sherm Bristow, who also served a long tenure as athletic director at Gilman in addition to teaching and coaching Holley. “There are a handful of people in my opinion who are exemplars of all that Gilman stands for and for which every alumnus should be proud. Timmy Holley is in that special group.”

Holley's commitment to Gilman did not end when he stepped away from the athletic department. Following a brief sabbatical in 2018, he joined the school's Development Office as Director of External Relations before returning to the classroom and coaching ranks full-time in 2023 as an Upper School English teacher.

Throughout his career, Holley became the only person in Gilman history to serve as Director of Athletics while also leading the school's varsity football, basketball and baseball programs as head coach.

In addition to his athletic accomplishments, Holley has been recognized repeatedly for excellence in education and service, receiving numerous honors from Gilman, including the Dunn Fellowship, Broadus-Hubbard Award, Russell Chair, Thomas Chair, Reipe Sabbatical and the May Holmes Service Award.

Before embarking on his distinguished career in education, Holley served his country with distinction. Commissioned as a United States Navy officer in 1981, he was awarded Commendation and Service medals for his work with the Multinational Peacekeeping Force in Beirut, Lebanon. He later served nine years in the U.S. Navy Reserve, reaching the rank of Lieutenant Commander.

A graduate of the University of Pennsylvania, Holley earned a bachelor's degree in English while competing as a four-year member of the Quakers baseball program and participating in the Naval ROTC program.

His athletic achievements began long before college. As a student at Gilman, Holley was one of the school's most accomplished multi-sport athletes. He earned the William Cabell Bruce Prize as Gilman's top student-athlete in 1977 and captained the football, basketball and baseball teams during his senior year.

On the football field, Holley led Maryland in rushing in 1976, earning first-team All-State honors and Player of the Year recognition. On the baseball diamond, he twice captured the Alumni Baseball Cup as Gilman's top player.