I was tempted to put the Trail Blazers as losers here. I decided instead to go with their star player, Damian Lillard. He lost some of his best teammates in CJ McCollum, Norman Powell, and Robert Covington for peanuts in exchange. While the Blazers carved out a ton of cap space, presumably to pursue a max free agent during the summer, the question is: what max free agent wants to go to Portland? Lillard is entering the downslide of his career, and he is further away from a championship than he has ever been with the Blazers. Furthermore, one of the main contenders he could have been traded to, the 76ers, traded for James Harden instead. Now, Dame is stuck on a team that is unlikely to contend for a while, and he has no real path to joining a contender.