by Rob Dinerman, College Squash Historian
A four-time first-team All-American at Columbia University, where he won the 2017 Individuals crown, was a finalist in 2015 and led the Lions to their only Ivy League championship during his senior 2017-18 season, Osama “Sam” Khalifa is known today not only for his outstanding college career but also for his meteoric rise up the SDA pro doubles tour to the No. 1 end-of-season ranking in 2023-24, which culminated a season in which he won both the SDA Player of the Year Award and (with partner Chris Callis) the SDA Team of the Year Award.
As a highly touted junior player, Khalifa was ranked in the very top tier and won junior championships in Europe in a number of the age-group categories, following in the footsteps of his older brother Amr, who himself won the college Individuals crown in 2013 and was runner-up in that event to current PSA No. 1 Ali Farag one year later. The Khalifas are only the second pair of brothers to win this prestigious championship. The Ezra brothers, Adrian and Dan, were the first, having reached eight consecutive Individuals finals (winning four) while representing Harvard from 1991-98.
After spending his final two high school years at Deerfield Academy – where he dominated the field in the New England Interscholastic tournament both years – Khalifa reached the finals of the 2015 college Individuals as a freshman before losing to Bates College star Ahmed Abdel Khalek. Although Khalifa had to withdraw from the 2016 tournament due to an early-round back injury, he experienced outstanding success both on and off the court in 2016-17 by surging through the Individuals draw, decisively defeating Rochester No. 1 Mario Yanez in a straight-game final, and attaining a 4.0 grade-point-average academically.
During his college career, the Columbia men’s roster was getting increasingly strong, due to the recruiting efforts of its longtime head coach Jacques Swanepoel, who had introduced himself to Khalifa during a junior tournament in Europe when Khalifa was only 14 years old. By the beginning of the 2017-18 season, the Lions’ lineup, led by Khalifa (who played No. 1 throughout his entire four years) and also featuring such standouts as Velavan Senthilkumar, Seif Attia and Carter Robitaille, was the strongest it had ever been, and in mid-January they defeated Harvard 5-4 (the first-ever Columbia victory over the vaunted Crimson), with Khalifa notching the deciding fifth point with an 11-9 fifth-game win over Saad Abouaish. Columbia then went undefeated for the remainder of the Ivy League schedule to capture the first (and, to this point, only) Ivy League pennant in the history of Columbia squash.
In the season-ending Potter Cup tournament, the Lions outplayed the University of Rochester 6-3 to advance to the semifinals (also for the first time), where they lost to a revenge-minded Harvard squad but rebounded with a 7-2 win over St. Lawrence in the third-place playoff. Khalifa’s five-game comeback victory over St. Lawrence star Ahmed Bayoumy (one of three 3-2 Columbia wins that day) represented the last match of his outstanding college career since the grueling three-day stretch (during which he had gone undefeated against a trio of All-American opponents) had left him too depleted to compete in the Individuals just five days later.
He received several honors at the end of that season, including his third consecutive Ivy League Men’s Player of the Year Award (preceded by the Ivy League Rookie of the Year Award he won in 2014-15), the William V. Campbell Performer of the Year Award (given to Columbia’s top male senior athlete) and the John Skillman Award, the most significant honor bestowed on a male squash player by the College Squash Association.
Throughout that extended time frame, Khalifa had never even seen a doubles court and only knew that the game existed from Swanepoel, who played on the SDA tour before and after the college season during the mid-twenty-teens. Khalifa played doubles for the first time during the summer of 2019 as a member of the Summer Guest program at the Racquet & Tennis Club in New York, where Khalifa was pursuing a career in sales and trading. He played a handful of times (borrowing a doubles racquet from the pro shop) without any intent of becoming serious about the sport.
Shortly after becoming a full member at Racquet & Tennis in Autumn 2021, however, he entered his first-ever doubles tournament – the Silver Racquet Invitational, a highly regarded open/amateur competition – playing the right wall with his left-handed partner Josh Hughes, and during both this event (where they lost fairly early) and in the few that followed, he became fully aware that doubles was a vastly different game, and that tactics that had worked well for him in singles did not have anywhere near the same success when he tried to transfer them to the doubles court.
Paradoxically, this potentially deflating realization instead had a powerful motivational effect. By that winter, Khalifa’s game had improved enough for him to enter his first SDA tournament (the venerable Johnson Memorial in Brooklyn Heights in February 2022. Throughout the remainder of that season and the 2022-23 campaign that followed, Khalifa, who by then had switched to the left wall, where the same compact backhand swing that had been one of the trademarks of his singles game was well suited to the fast pace of doubles squash, steadily rose through the ranks. During the first few months of the 2023-24 campaign, he won two tournaments – Sleepy Hollow with James Bamber and the North American Open with Chris Callis, both of them first-time SDA partners – following which Khalifa and Callis lost the Heights Casino final to James Stout and Scott Arnold but won a rematch in the finals of Boston a few weeks later.
Indeed, the Stout/Arnold vs. Khalifa/Callis rivalry came to define the second half of the 2023-24 men’s SDA season, to the point where the late-April Kellner Cup in Manhattan would be for the No. 1 end-of-season team ranking, just as had been the case the last time this biennial tournament was held in April 2022, when Callis and Manek Mathur outlasted Stout and Arnold in five games, thereby clinching the No. 1 spot for that season.
In the clash between the two top teams before a full gallery at Racquet & Tennis, Callis and Khalifa won the first game and led 13-4 in the second. They wound up winning that game 15-11, but the momentum Stout and Arnold acquired late in the game continued when they took the first six points of the third (a 13-2 run overall) and closed it out 15-12. Khalifa and Callis bootstrapped their way to an imposing 13-8 lead in the fourth, but Stout and Arnold made yet another eleventh-hour charge to 13-14. Callis and Khalifa, who had been so sharp and energetic during the match’s first two games, looked depleted by the toll that the two-hour battle had taken and, by their own subsequent admission, would have been at a significant disadvantage had the match extended into a fifth game, especially in light of how assertive Stout had become by that juncture and the degree to which Arnold had almost completely eliminated his early-match racquet errors.
But at this crisis moment, Khalifa circled around an over-hit Arnold cross-court and conjured up a forehand reverse-corner from the back wall that slowly and mesmerizingly drifted into no-man’s-land, creating just enough momentary confusion between his opponents as to who should retrieve it for neither of them to react in time to prevent the ball from taking a second bounce. The Kellner Cup has had some memorable endings over the years – particularly when the No. 1 team ranking has hung in the balance – but 2024 ranks right with the top of that list. That outcome vaulted Khalifa to the No. 1 individual SDA ranking, making him the first Egyptian-born player to attain that standing. He consolidated it even further by teaming up with Kyle Martino to win the Big Apple Open, the first important tournament of the 2024-25 season, in a tight four-game final over Bamber and Zac Alexander.
Khalifa credits his college experience – citing how high the level of play had become throughout his years at Columbia during the twenty-teens, especially in the competition among the respective No. 1 players on the top teams – for giving him the racquet skill, the conditioning and the ability to make tactical changes on the fly that have served him so well on the SDA tour. He’s also a strong advocate for the SDA, particularly for elite college players who are career-focused but still want an outlet for their competitive sports drive. Unlike players on the PSA tour, most on the SDA maintain separate professions, as is the case with Khalifa, who now works for Citadel Securities in Fixed Income Sales and notes another clear benefit, saying, “Virtually every single client and job I’ve had since graduating from Columbia has come through a squash connection.”
With his breathtaking ascent from an early-round loss in his doubles tournament debut at the 2021 Silver Racquets (both of whose 2022 and 2023 editions he subsequently won with Matt Henderson and Elroy Leong, respectively) to the No. 1 ranking on the pro tour in just 30 months while also carving out a successful Wall Street career, the still-young Khalifa has even brighter prospects for the years ahead and has illuminated a path for other top-tier college squash players to follow.
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Rob Dinerman has written 18 books about squash, five of which are Histories of the sport at various top-tier colleges, including A Century Of Champions: 100 Years Of College Squash, 1923-2023, which was released in March 2024. His most recent book, Racquets At Rest: Remembering 40 Lives That Shaped The Game Of Squash In America, was released in February 2025.
