Jordan Riley's accolades as a high school forward from Brentwood (NY) High School were notable: 31 points, 6.5 assists, 5.5 steals and 3.8 blocks per game as a senior, named Mr. New York Basketball and Gatorade State Player of the Year in 2021. Selecting an offer from Georgetown over the likes of Kansas, Connecticut, Pittsburgh, St. John's in the summer of 2020, Riley told Sports Illustrated that his relationship with Ewing drove the decision.

"I can trust him as somebody that can look after me," he said.

Riley's upward trajectory was sidetracked by injuries as a freshman, where he played played only nine games early in the season before electing for surgery to repair a torn labrum. As a sophomore, Riley was the odd man out of a Ewing lineup that relied heavily on recent transfers. Following a mid-season injury to Jay Heath, Riley started nine games, averaging 7.7 points with a season high of 18 points on 8 for 12 shooting versus Villanova.

Whether due to a recurrence of the injury or just lost confidence, Riley's shooting numbers sank precipitously. Beginning with a 1 for 5 showing before friends and family at Madison Square Garden versus St. John's on January 29, Riley finished the season shooting a combined 4 for 28 (.125) in his final nine games of the season, 0 for 12 from three point range. Riley was 0 for 3 in 21 minutes during the season finale at the Garden versus Villanova and was visibly discouraged in the waning moments of that game.

Riley announced a transfer five days after that game.