In a timeline where the Jae Crowder trade went down, there's no way one can say the move to add Damian Lillard was worse for the Milwaukee Bucks. Nevertheless, ESPN's Zach Kram highlighted the Lillard deal, calling it Milwaukee's worst roster move of the 2020s in a recent article. One could make an argument, sure, but the Crowder trade still stings due to how poorly it went.
The Milwaukee Bucks' Jae Crowder trade cannot be forgotten
Knowing what the Bucks knew at the time, opposing teams would have done the Damian Lillard deal if they had the chance. Who wouldn't want to pair two top 75 players together to forge one of the best one-two punches in the NBA? At the time, it was a dream. Did things work out? Not exactly. Not with a title at least, but that doesn't mean it was flat-out disastrous.
One could argue that because there was no title, Jrue Holiday, a first, and two pick swaps were far too steep for the guard, knowing what is known now.
Lillard was a two-time All-Star, helped the Milwaukee Bucks win the NBA In-Season Tournament (as insignificant as it may be in the bigger picture), and formed the highest-scoring duo in the league as Giannis Antetokounmpo's partner in crime. On the subject of Giannis, the Greek Freak also signed an extension after Lillard came aboard, so the trade was valuable for that alone.
The Crowder trade didn't feature any of that.
Milwaukee gave up a total of five second-round picks to get Crowder. At the time, it felt steep, but at the same time, necessary to get the Bucks their ideal P.J. Tucker replacement. Crowder had all of the tools to fill this role, but he simply never found his footing in Milwaukee. Even when he was healthy, he looked like a shell of the version the Bucks thought they were getting.
While the Damian Lillard trade largely didn't work out because the guard got injured during both of his trips to the NBA Playoffs, Crowder simply didn't play well. During eight playoff games in two years with the Milwaukee Bucks, the veteran forward, known for his postseason experience, averaged a measly 10.4 minutes per game. That's not worth five second round picks.
The Crowder trade has been haunting Milwaukee for quite some time. Due to the lack of second round picks, they haven't been able to make many moves around the edges. Cam Whitemore just got traded to the Washington Wizards for two seconds. He would have been a nice young player to take a flyer on as the Milwaukee Bucks try to get the small forward position figured out. The Bucks could've also added some second round draft talent.
Even knowing what the world does now, the Lillard trade is not Milwaukee's worst deal of the 2020s. The Jae Crowder deal will hold that title for now.
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