The Milwaukee Bucks knew a change was needed heading into this offseason.
The team, clearly wanting to appease and please their star Giannis Antetokounmpo, went out and acquired multi-time All-Star Damian Lillard from the Portland Trail Blazers back in 2023. The hopes were that the duo would lead the Bucks to another title.
Lillard was quite good — averaging 24.3 PPG and 24.9 PPG in back-to-back years, plus seven assists a contest. However, upon tearing his Achilles tendon in the first round of last year's playoffs, his tenure with the team quickly came to an end.
Bucks owner Wes Edens on the Damian Lillard release:
— BucksRealm (@BucksRealm) September 29, 2025
"Damian was owed a lot of money. He was not gonna play basketball this year. So then, stretching out that money over 5 years, it became a much more digestible number.
When you have a player of Damian's caliber who is not… pic.twitter.com/YmkXnDM21P
Lillard ended up being waived by the franchise this past July despite still being owed more than $100 million. With the team opting to use the stretch provision on Lillard's deal to open up financial flexibility, the team then went out and inked free agent center Myles Turner to a four-year deal.
With Lillard, Pat Connaughton, Khris Middleton, and Brook Lopez now out the door since the start of the calendar year, the team looks vastly different this season compared to opening night in 2024-25.
Milwaukee Bucks owner Wes Edens recently commented on the roster shake-up pertaining to the Lillard decision.
"Damian was owed a lot of money," Edens said. "He was not gonna play basketball this year. So then, stretching out that money over five years, it became a much more digestible number.
When you have a player of Damian's caliber who is not gonna play, that's a big gap. We felt like it was very rational after thinking long and hard."
To be fair to the owner, the Bucks were essentially strapped money-wise given Lillard's deal. The team also doesn't possess requisite draft capital/assets to alter their team in any substantial way going down the trade route given the fact that much of their cache of picks/swaps went to Portland when acquiring Lillard in the first place.
It also ended up working out for Lillard. A lifer in Portland before the deal, Lillard — a West Coast native — clearly wanted to head back to a more comfortable situation closer to family. Upon being released by Milwaukee, he did ink a three-year deal to return to Rip City.
Much of this decision will be graded on how Turner performs for the Bucks, and by proxy how the team fares the next few years. If the team collapses, those pick swaps possessed by Portland could end up coming back to bite Milwaukee in a serious way.
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