Milwaukee Bucks: Trading Damian Lillard to retool around Giannis
For the Milwaukee Bucks, the easy answer to this question is probably Giannis Antetokounmpo. However, despite how much this narrative wants to be pushed, I'm not sure how likely or realistic it is that the Bucks are going to move toward a position of trading Giannis this offseason. Because of that, I do believe that the better answer to a path in which the Bucks could make some serious noise this offseason revolves around a Damian Lillard trade.
In one final attempt to surround Giannis with a stronger supporting cast, it would make much more sense for the Bucks to try and trade Lillard this offseason. If the Bucks could pull it off, it would certainly help this team in their attempt to climb back up to the top of the mountain in the Eastern Conference. Whether or not they can pull it off is an entirely different question. However, the motivation will certainly be present.
Minnesota Timberwolves: Trading Rudy Gobert to open more cap space
The Minnesota Timberwolves are always going to be a team of relevance in the Western Conference as long as Anthony Edwards is still on the roster. However, if this team is going to reemerge as a championship contender in the future, the argument can be made that they need to reshuffle the supporting cast around their superstar guard. One way the team could open up some added financial flexibility is by trading Rudy Gobert.
The defensive-minded center is due roughly $110 million over the next three seasons. It's going to be increasingly hard for the Wolves to significantly improve their roster if they are having to pay Gobert close to $40 million per year. It does seem like trading Gobert is a path the Wolves will eventually go down. If the Wolves were to suddenly make him available this offseason, it could certainly tip the scales in the Western Conference hierarchy.