Donovan Mitchell, Cleveland Cavaliers
From an objective standpoint, it would be shocking if Donovan Mitchell ended up re-signing long-term with the Cleveland Cavaliers. This is not generally something that happens often in the NBA. Especially not something that has happened often in recent history. Just think. Mitchell was traded to a place he didn't initially want to go - Cleveland. He's playing nice, keeping his head down, and working. However, with the opportunity to leave in free agency after the 2024-25 NBA season, I have a hard time seeing Mitchell bypass that power.
Right now, for the first time in his career, Mitchell has the chance to dictate what comes next in his career. I don't think he's going to settle for a confusing fit with the Cavs. That's not a knock on Cleveland, just basic facts. Mitchell is 27 years old and doesn't have time to wait another season or two for Darius Garland and Evan Mobley to hit their prime years. Mitchell needs - or should - be competing for a title now.
And if Mitchell declines to sign an extension again this offseason, that's when I believe the Cavs will pivot toward trading him. I predict that's exactly how this summer will play out in Cleveland.