He was previously serving as a consultant to Tom Izzo at Michigan State after being let go as head coach with Georgia Tech.

Naval Academy where he played on the Navy team that featured David Robinson and advanced to the Elite Eight of the NCAA tournament.

On March 16, 2015, Georgia Tech announced that Gregory would continue as head basketball coach for another year, despite the fact he never had a conference finish higher than ninth.

After a 5th consecutive losing record in the ACC, Georgia Tech Athletic Director Mike Bobinski announced on March 25, 2016, that Gregory would not return for the 2016–17 season.

It posted a 7–11 record at the Yuengling Center (formerly the USF Sun Dome), but struggled away from home, collecting just three wins away from Tampa.

USF also was benefitted by Gardner–Webb transfer Laquincy Rideau, who came off a redshirt season in 2017–18 and Alexis Yetna's addition to the hardwood.

Former Mississippi State power forward Prince Oduro and Texas Tech center Russel Tchewa joined the squad and the Bulls brought in consensus four-star combo guard Caleb Murphy to bolster a team that just lost two seniors and one outgoing transfer.

[13] It was announced, on January 4, 2022, that Gregory's contract would be extended until the 2025–26 season, as a part of 14 overall head coach extensions executed by USF Vice President of Athletics Michael Kelly.

[14] After enduring a fourth straight losing season, on March 10, 2023, Gregory was relieved of his duties as South Florida head coach.

[15] On June 10, 2024, Gregory was hired as the Phoenix Suns' vice president of player programming, joining former Long Island Nets general manager and Brooklyn Nets vice president of strategy Matt Tellem as the newest front office hirings.

[16] He would join the team that's currently owned by Mat Ishbia, a player he had previously worked with while as an assistant coach for Michigan State University during their 1999–2000 NCAA championship season run.