Mark Pope’s work in the transfer portal is far from over—and this time, it won’t come easy.
While Justin McBride has grabbed most of the headlines during his current visit to Lexington, Kentucky is quietly pursuing another impactful addition. Dayton transfer guard De’Shayne Montgomery has now entered the picture, giving the Wildcats a potential boost in the backcourt. But unlike some other recruitments, this one comes with serious competition—especially from within the SEC.
Montgomery, a 6-foot-4 guard and former Georgia Bulldog, is no stranger to the conference. After a strong junior season at Dayton, where he averaged 13 points and four rebounds while shooting an efficient 49% from the field, he’s become a sought-after name in the portal. His defensive ability also stands out, as he averaged over two steals per game and consistently created transition opportunities.
Kentucky, however, isn’t the only program making a push. Ole Miss and South Carolina are both expected to be heavily involved, while Montgomery has already taken visits to NC State and Louisville. A return to the SEC feels likely—but where he ends up could depend heavily on the role he’s offered.
With the Wildcats, Montgomery would likely come off the bench behind Alex Wilkins at the two-guard spot, while also having the flexibility to slide to the wing in smaller lineups. That versatility fits well within Pope’s system, but it may not offer the same level of opportunity as other programs pitching a larger role.
That’s where things get complicated. Kentucky has the name, the resources, and the exposure—but in today’s transfer landscape, playing time and fit can outweigh reputation.
If Pope wants to secure Montgomery, it’ll take more than just interest. He’ll need to outwork fellow SEC programs and make a convincing case that Lexington is the right place for the next step in the guard’s career.
