If the Milwaukee Bucks do trade Giannis Antetokounmpo over the offseason and enter a rebuild phase, they'll once again run smack into their largest self-created problem. On the Game Theory Podcast w/ Sam Vecenie, the host highlighted how last offseason's controversial decision will continue to haunt them:
"We have, if they decide to rebuild, $22 million of dead money on the books for the next four years after this one from the Damian Lillard waive-and-stretch. That $22 million, as we've seen, if you're a rebuilding team, that really hinders you from taking back bad money in contracts to start to accumulate more and more draft capital."
It would have been better if the Bucks' decision to do so didn't look as bad as it does right now, but Myles Turner has been very underwhelming this season. It's not his fault, of course, that Milwaukee made the kind of leap it did to sign him (to not even reach the play-in tournament, mind you), but it puts his play under an even harsher spotlight.
Turner could turn things around and, hopefully, increase his trade value in the process, but the team signed him to convince Giannis to stay and win a title. In case you didn't already know, neither of those odds looks so great.
Bucks could have yet another reason to regret Damian Lillard move
Anything can happen with Antetokounmpo. Milwaukee could luck into a top draft pick that it can use to make a trade to show him why he should consider signing an extension, or use it to select the kind of player it wants to build around if he leaves.
It feels like the Bucks won't be able to delay the rebuild any longer. Milwaukee will need to nail its first-round pick, as it won't have another until 2031. That should change with a Giannis trade, although they might not get the kind of haul they want to kickstart the future.
As Vecenie said, another way to add to their draft capital would be to take on bad contracts in exchange for draft capital (like Sam Presti and the Thunder did expertly), but given that the Bucks will pay Dame over $22 million through the 2029-30 season, that's a chunk of cap space they can't use to their advantage.
No team was going to take on Lillard's contract after he tore his Achilles in the 2025 playoffs, so Milwaukee wouldn't have been able to move his salary off the books (hence why it resorted to a waive-and-stretch). In retrospect, though, the Bucks would've been better off paying him the $54.1 million he was owed this season to rehab, and then paying him $58.6 million in 2026-27.
Regardless of how the offseason plays out, Milwaukee will still be stuck with a constant reminder that it resorted to a desperate measure to land Turner. If the rebuild happens, the Bucks will wish they could use the money they'll pay Dame to grow their asset pile, which you can't even classify as a pile right now.