The Milwaukee Bucks waived and stretched Damian Lillard's contract in a move that allowed them enough cap room to sign former rival Myles Turner. Milwaukee now has dead money for the next five years, owing Lillard roughly $22.5 million annually. That's perfect timing for the Portland Trail Blazers, who have the Bucks' 2029 first-round pick due to trading Lillard in the first place. The exception is that Portland agreed to send over the second most favorable of the 2029 first-rounders between Boston, Portland, and Milwaukee to the Washington Wizards in the Deni Avdija deal.
A lot can change between now and 2029 in the ever-evolving NBA, but it's becoming increasingly likely that Washington will receive the Blazers or Celtics pick. Portland's young core will be in its collective prime by then, while Boston just quietly had a franchise-altering offseason as they were able to shed the salaries of Jrue Holiday and Kristaps Porzingis.
Meanwhile, Milwaukee continues trending in the wrong direction.
Bucks' desperation to keep Giannis continues to backfire
Fred Katz of The Athletic compared the Bucks' decision to waive Lillard to the Suns waiving Bradley Beal, calling it an unsafe move for two desperate teams.
"Typically, this mechanism has been used for lower-salaried players, not ones owed anything close to as much as Lillard or Beal. The reason why: It's not safe. The Bucks and Suns will owe money to players not on their roster through the end of the decade, harming their flexibility in the process," Katz wrote.
For the Bucks, that desperation stems from trying to add enough talent (Myles Turner) to keep Giannis Antetokounmpo in Milwaukee.
The Bucks signed Turner to a four-year, $108.9 million deal, addressing their most significant need after the departure of Brook Lopez. But it's reminiscent of the Blazers signing Jerami Grant to keep Damian Lillard happy in 2023. Of course, Turner's contract isn't as disastrous, but these aren't needle-mover additions to help sway superstars.
Now the Bucks have to pay Lillard and Turner for multiple seasons rather than simply getting off Lillard's salary earlier, limiting their flexibility to add a true co-star to make Milwaukee a contender again. This myopic decision and Milwaukee's aging and flawed roster led CBS Sports' Sam Quinn to rank the Bucks' 2029 first-round pick as the second most valuable traded draft asset.
"The 2026-27 Bucks technically benefit from the Damian Lillard waiver, as Lillard would have cost them well over $50 million in this season before he was waived, but will now cost them only $22 million. In 2029, however, the Bucks will still owe $22 million in dead money for Lillard that otherwise would have been off their books. Sure, Myles Turner will still be under contract, but he will be 33 at that point," Quinn wrote.
So let's recap this massive fleece by the Blazers: they landed building blocks Toumani Camara and (later) Deni Avdija as part of the Lillard trade. Two seasons later, they got Lillard back on a team-friendly three-year, $42 million deal. The draft picks Milwaukee sent to Portland have yet to be conveyed. And when they do, they will still owe Lillard $22 million and have to pay an aging Turner who just averaged 10.6 points and 4.4 rebounds in the Finals.
If I'm Giannis, it's hard to feel confident about the direction this franchise is headed in. The Bucks' desperate moves could be the very thing that drives him out of town.