Osama Khalifa ’14 is one of Deerfield squash’s most notable alumni. Born and raised in Cairo, Egypt, Khalifa’s squash career began when he was very young. In 2008, when he was 13, Khalifa made a name for himself in the squash world by winning the British Junior Open Squash Under 13 age group.
He continued to have large successes throughout middle school and high school, including his time at Deerfield. After coming as a new junior in 2012, he never lost a single match in his two years competing for the Big Green. However, he was not only a strong player, but also a captain and friend.
Current boys varsity squash captain Danny Finnegan ’17 recalls his overlapping time with Khalifa: “He was a leader my freshman year at Deerfield, even coming to outside tournaments to coach me, when he could have been doing anything he wanted in his free time. He would get on court with Robby [Dewey] and I and hit with us and help our game—really a team-first guy.”
While at Deerfield, Khalifa also excited the campus on the weekends. In the fall of 2013, Khalifa invited Seif Attia from Avon Old Farms School to come play. The Dewey Squash Center was packed with 400 students as Khalifa took out Avon’s number one.
Finnegan remarked, “I can’t remember a sporting event since that has drawn that many fans at Deerfield, and all for one player.”
After graduating from Deerfield Academy in 2014, Khalifa went on to play squash at Columbia University. He received Ivy League Rookie of the Year in 2015, and two time first team All-Ivy League and All-American in 2015 and 2016. In 2016, he was the Ivy League Player of the Year. This past fall, Finnegan and Deerfield head coach Michael Silipo went to support Khalifa as he won the NCAA squash championships at Dartmouth, taking down University of Rochester’s Mario Yanez in three games: 11-1, 11-6, 11-5.
Finnegan described his play: “He takes one step up or down the court and he’s already at the ball. He cuts everything off and has the best deception I’ve ever seen.”
Coach Silipo shared his experience coaching Khalifa here at Deerfield: “Osama is the best player I have ever coached at this level over my 39 years of coaching squash… he makes it look so easy.”