Milwaukee Bucks: Damian Lillard - 2 years, $102 million
It may be a bit strange to hear that the Milwaukee Bucks should look to trade Damian Lillard this offseason, but considering their circumstances moving forward, this may not be that outlandish of an idea. Assuming the Bucks aren't going to make this miracle playoff run this season, this is a franchise that will almost have to improve the roster if they're going to have any shot to reemerge as a contender in the East next season.
Finding a natural path toward doing so without trading Lillard could be difficult. Due $50-plus million over the next two years is going to put the Bucks at a disadvantage in terms of their chances of upgrading their roster. Considering the duo of Lillard and Giannis hasn't clicked all that well either, perhaps trading Lillard could be the key to the Bucks finding much-needed flexibility moving forward.
Minnesota Timberwolves: Rudy Gobert - 3 years, $110 million
Even though the Minnesota Timberwolves did end up taking a bit of a step back this season, I wouldn't place a ton of blame on Rudy Gobert. However, at the same time, because of his huge contract, he's probably going to make life difficult for this front office to make a big move to upgrade their roster heading into next season. In fact, the argument can be made that if the Wolves are going to successfully upgrade their roster this summer, they may need to start with a trade of Gobert.
The acquisition of Gobert hasn't been a trainwreck for the Wolves, but it also hasn't been a slam dunk. At some point soon, you'd have to imagine the Wolves are going to pivot away from Gobert. It could make a ton of sense for the Wolves to go down that path sooner rather than later.