Damian Lillard, Milwaukee Bucks
The odds probably aren't great that Damian Lillard would demand a trade for a second straight season. However, considering he's in a place he didn't exactly want to be in the first place and the fact that the Milwaukee Bucks drastically underperformed this season, I suppose we can't exactly take this possibility off the table. It would create quite a chaotic summer if Lillard did ask the Bucks to trade him this summer. Not only would it send shockwaves across the league but it would also make a mess of Milwaukee's situation moving forward.
At least in part, the acquisition of Lillard was an attempt to keep Giannis Antetokounmpo bought into the future. While this move hasn't worked as perhaps the team thought it would, there's still a chance the team can right things heading into the next season or two. However, if Lillard were to demand a trade, that possibility would be pretty much nuked.
Even though it would be shocking for Lillard to demand a trade for a second straight season, it would make for an intriguing offseason for every other team not named the Bucks.