
After missing out on point guard Donovan Dent, who committed to UCLA, the Kentucky Wildcats have shifted their attention to other options in the transfer portal. One of the most promising candidates is Ja’Kobi Gillespie, a skilled playmaker who entered the portal on Monday. As Kentucky looks to strengthen its backcourt, Gillespie has become a key target in an increasingly competitive transfer market.
Gillespie’s Path: From Belmont to Maryland
Gillespie began his college career at Belmont, where he quickly made an impact, earning Missouri Valley Conference All-Freshman honors. In his sophomore year, he continued to shine, averaging 17.2 points and 4.2 assists per game.
Seeking a bigger challenge, he transferred to Maryland, where he transitioned smoothly into the Big Ten. During the 2024-25 season, he started all 36 games for the Terrapins, averaging 14.7 points, 4.8 assists, and 2.8 rebounds per game, with a 40.7% shooting rate from three-point range.
His efforts played a key role in Maryland’s Sweet 16 run in the NCAA Tournament. Additionally, Gillespie showcased strong defensive abilities, ranking third in the Big Ten with 1.9 steals per game. His successful transition from a mid-major to a Power Five conference demonstrates his adaptability and competitive edge.

Kentucky’s Interest and Potential Role
According to Kentucky Sports Radio, Wildcats head coach Mark Pope has already reached out to Gillespie through his father, expressing clear interest in the talented guard. If Kentucky manages to secure him, Gillespie would provide an immediate boost to a roster in transition.
His playmaking ability, knack for creating scoring opportunities, and consistent three-point shooting would mesh well with Pope’s offensive system. Furthermore, Gillespie’s defensive strengths would help Kentucky compete in the tough SEC. With experience against top-tier competition, he could offer valuable leadership and reliability in the backcourt.
A Competitive Recruitment Process
While Kentucky has shown early interest, Gillespie’s proven track record makes him a highly sought-after transfer. Several programs are likely to pursue him, each offering unique opportunities that align with his strengths.
His decision will likely depend on factors like system fit, playing time, and development potential. If Kentucky successfully lands Gillespie, it would be a significant addition to Mark Pope’s first offseason, adding experience and depth to the Wildcats’ backcourt and setting them up for a competitive 2025-26 season. As recruitment continues, Gillespie’s decision will be closely watched by programs eager to add an impact player to their lineup.
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