When the Milwaukee Bucks acquired Damian Lillard in a trade in 2023, it was a bit of a stunner. Lillard was discontent with the Portland Trail Blazers, the only team he had ever played for, and was looking for a trade, ideally to the Miami Heat. Yet it was the Bucks that emerged as the winner of the Dame sweepstakes. There was reason to be excited in Milwaukee. At their peaks, a combination of Lillard and Giannis Antetokounmpo could do some damage, particularly on the offensive end of the floor.
Unfortunately, we rarely got to see that unfold on the court. Lillard and the Bucks secured the No. 3 seed in the Eastern Conference during his first season on the team, though the Bucks lost to the Indiana Pacers in the first round. This past season, Lillard had deep vein thrombosis—also known as a blood clot—in his right calf. He tried to come back for the postseason but tore his Achilles tendon in Game 4 of the first round, likely keeping him out for all of this upcoming season.
The Bucks lost in five games, again to the Pacers. And the team has shaken up its roster this offseason. Milwaukee poached Myles Turner away from the Pacers with a four-year, $107 million contract, though it had to waive Lillard to do so.

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Because of the way NBA contracts are structured, the Bucks still owe Lillard all of his remaining salary, which is $113 million. As part of the stretch provision, that payment can spread out across the salary cap over the next five years.
Pacers reporter Alex Golden said Indiana offered "well north" of $20 million per year, though it seems like the Pacers may not have wanted to include the fourth year in Turner's deal and move into the luxury tax. Instead, he'll make close to $27 million annually for a divisional rival.
Even though Turner's deal is for $107 million, the Bucks are in essence paying $220 million in order to sign him. They wouldn't have been able to make this move without releasing Lillard, though they'll have to pay him handsomely, even if he joins another team.
It's a shocking end to the Lillard era in Milwaukee, less than two years after it began. He's about to turn 35, and Achilles injuries aren't easy to come back from, but this could very well be extra motivation to bounce back with another contender.