If Damian Lillard signs with the Boston Celtics, a team with rumored interest in him, it would be the second time in the past few years that a former Milwaukee Bucks All-Star point guard joined them. Just like with Jrue Holiday, there would be no shortage of chatter from NBA talking heads about Milwaukee's decision to part ways with the guard and let him join a key rival, though those talks will more than likely be misguided (again).
Holiday, Lillard could be on similar paths after leaving Bucks
Milwaukee's decision to trade Holiday wasn't an easy one. He meant a lot to the team and the city, even beyond helping them win an NBA Championship. However, they had a chance to move him in a deal for one of the 75 greatest players in league history, and they took it. Plenty of teams would make the same move.
The Holiday-Bucks discourse from his time in Boston has always made little sense. Did Holiday win a title? Yes, but he was a fourth or fifth option during that title run. He had far less responsibility than he ever did in Milwaukee. Media members and fans also overlook Holiday's poor playoff showings with the Bucks in 2022 and 2023, which fueled the decision to trade for a player of Lillard's caliber.
Bashing the Milwaukee Bucks' decision to trade for Lillard simply because Holiday saw success as a Celtic in a lesser role has always been a foolish argument.
In Lillard's case, the seemingly growing disconnect between him and the Milwaukee Bucks prior to his historic waive and stretch will likely be overlooked. Per The Athletic's Eric Nehm and Sam Amick (subscription required), if the guard had not torn his Achilles, sources indicated that there would have been talks about whether Lillard wanted to remain in Milwaukee moving forward.
In that case, it makes plenty of sense to cut ties with the guard in order to add a perfect Brook Lopez replacement for the foreseeable future in Myles Turner. The Milwaukee Bucks need players who are all in on this team, and they've certainly got that in Turner. Where Lillard goes from here will be his choice, and he's apparently "elated" about that. He seemingly wasn't long for Milwaukee.
If Damian Lillard goes to Boston, so be it. It won't be Milwaukee's fault that he went there. Just like with Holiday, other teams had an opportunity to get him, but Boston just made the best pitch, and they deserve credit for that. Context will always be crucial. If Lillard didn't want to be with the Bucks, letting him go makes sense, even if he ends up with an Eastern Conference rival.
Even so, the talking heads will have another misguided field day if this goes down.
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