He transferred to Elder High School for his senior year and in 1993 helped lead the team to a Division I state title.

As an assistant at Wake Forest, Kelsey coached a number of players who went on to have successful professional basketball careers, including NBA All-Stars Chris Paul and Jeff Teague.

The 2016–17 Eagles claimed a share of the Big South regular season championship and defeated the Campbell Fighting Camels in the title game to earn Winthrop’s 10th trip to the NCAA Tournament.

In 2017, Kelsey was hired as the head coach at Massachusetts, but returned to Winthrop two days after accepting the position, citing personal reasons.

[19] His 75th win was also his last for the Cougars, an overtime triumph against Stony Brook in the Championship Game of the CAA Tournament.

[21] On March 28, 2024, Kelsey was named the head men's basketball coach at Louisville, agreeing to a five-year contract.

[23] In December 2012, after a game against Ohio State, Kelsey gave an impassioned speech about the Sandy Hook Elementary school shooting that had occurred just days prior.

During the game's press conference, Kelsey spoke out about the tragedy and said "Parents, teachers, rabbis, priests, coaches, everybody needs to step up.

At the game, each Winthrop player wore the name of a child killed at Sandy Hook on the back of their jersey.