2. Jimmy Butler
When the Chicago Bulls finally pulled the trigger on a deal that sent Jimmy Butler to the Minnesota Timberwolves in 2017, it signaled a true end of an era and the beginning of a full-scale rebuild. The Bulls would receive Zach LaVine, Lauri Markkanen, and Kris Dunn in return, a package that has actually panned out better than expected but still somehow doesn’t feel like enough to fill the void Butler left in our hearts.
Butler was dealt following the best scoring season of his career, as he averaged 23.9 points per game in 2016-17, which at first glance might make it seem like a perfect sell-high on the Bulls’ behalf. However, Jimmy has elevated the rest of his game so much since then that no sane person would argue 2017 was his peak.
Since then, Butler has taken the eventual NBA champion Raptors to the absolute brink in the final seconds of a 7-game playoff series in 2019 and single-handedly carried a depleted Miami Heat team to two wins in the NBA Finals in 2020. There’s just no denying that Butler is one of the NBA’s premier players these days, and the Chicago Bulls have to face the fact that refusing to offer him the extension he deserved was a massive misstep.
Jimmy Butler was the #1 option the Chicago Bulls had been searching for in a post-Derrick Rose world, but they gave up on him far too soon.
Knowing Jimmy is the type of player that thrives in the face of adversity, perhaps being let go by the Chicago Bulls provided the motivation he needed to improve in the first place. After all, he made it abundantly clear just how big of a mistake Philadelphia made by choosing to retain Tobias Harris and Ben Simmons over himself.
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Because it’s impossible to know if he would have taken these leaps in development without being traded in the first place, Jimmy only comes in second on this list, despite clearly being the best player among the bunch.
Even if Butler wouldn’t become the All-NBA talent he is now, wouldn’t it have been nice to watch a perennial All-Star actually play his career out in Chicago? Instead, Butler joins former teammates Derrick Rose and Joakim Noah as Chicago legends that ultimately had their legacies diminished by a horribly-incompetent front office.