Joe Cronin - Loser
The 2023 NBA offseason may not be remembered as the summer of Damian Lillard. Instead, Portland Trail Blazers general manager Joe Cronin managed to make it all about himself. But if the first half of this season is any indication, there could be a few regrets when it comes to the trade that he ultimately agreed to with Lillard. In total, the Blazers received Deandre Ayton, Toumani Camara, Malcolm Brogdon, Robert Williams, Golden State's 2024 1st round pick, Boston's 2029 1st round pick, Milwaukee's 2029 1st round pick, and two picks swaps from the Bucks (2028, 2030). That's a lot of substance with little to no value.
Let me explain why. The Warriors' 2024 first-round pick isn't likely to be in the lottery. They'll figure something out soon. Boston's and Milwaukees' 2029 1st round picks aren't going to be good with how bright their respective futures look with Giannis Antetokounmpo and Jayson Tatum, respectively. Ayton is having one of the worst seasons of his career and Williams is out for the season and the Celtics may have burned his knees out.
Camara has been a surprising bright spot for the Blazers this season but he's not a player with a star ceiling. Add in the fact that Scoot Henderson has not even been one of the five-best rookies in the league this season, and there's an argument to be made that Cronin completely mishandled the offseason.