Rick Pitino’s aggressive move for Donnie Freeman could end up creating a major advantage for Kentucky in the evolving NIL landscape.
Freeman is an elite talent capable of instantly raising the ceiling of any roster he joins. His offensive skill set makes him one of the most impactful additions in college basketball. However, his biggest concern has always been durability. A toe injury that required surgery limited him to just 37 games over two seasons at Syracuse, creating understandable questions about his long-term availability.
But health may not be Rick Pitino’s biggest concern.
The larger issue could be the NCAA’s possible move to a 5-years-to-play-5 eligibility model expected to be discussed this summer. If approved, it would allow more veteran players to return, creating major roster and NIL complications across college basketball.
Pitino recently addressed how difficult that situation could become.
“It would be pure chaos,” Pitino said. “Most teams have used 80% of their NIL. Next year makes sense. Now, don’t get me wrong, I would love to have my seniors back, but our NIL is just about finished.”
That comment highlights the real problem.
Programs are no longer just managing scholarship spots—they are balancing major NIL budgets. Spending more than $3 million on Freeman could leave St. John’s with less flexibility to retain or pursue experienced players like Zuby Ejiofor or Dillon Mitchell if the extra eligibility rule creates a flood of veteran talent in the portal.
That could work in Kentucky’s favor.
Mark Pope and the Wildcats may be in a stronger position than many programs because Kentucky has been more strategic with NIL spending across the roster. If extra eligibility becomes reality, UK could have more freedom to make stronger offers for returning players or major portal additions.
One player to watch closely is Otega Oweh.
Oweh is not projected in most NBA mock drafts, and ESPN currently lists him at No. 100 among available prospects, well behind teammate Malachi Moreno. Another season in Lexington could improve his draft stock, give him a larger offensive role, and allow him to earn more through NIL than he would likely make in the G League.
For Mark Pope, keeping Oweh for another year would be a huge win.
While some programs may struggle with roster imbalance and financial overextension, Kentucky could benefit from stability and flexibility. Pitino’s big-money gamble on Freeman may end up opening more doors for the Wildcats than expected.
If the NCAA approves the 5-year rule, college basketball could change quickly. Some schools may find themselves stretched too thin, while others like Kentucky could be perfectly positioned to take advantage.
