The Waive and Stretch: All The Angles Of The Damian Lillard Deal
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Damian Lillard Is Finally Traded
We have a deal! The Damian Lillard Saga has finally ended, with the Milwaukee Bucks landing his services and the Suns jumping in as a third team in the trade. The full details of the deal are as follows:
Milwaukee Bucks receive: Damian Lillard
Portland Trail Blazers receive: Jrue Holiday, Deandre Ayton, Toumani Camara, 2029 MIL 1st (unprotected), 2028 and 2030 MIL 1st round swap rights
Phoenix Suns receive: Jusuf Nurkic, Grayson Allen, Nassir Little, Keon Johnson
There’s a lot going on here, with all three teams involved making a major roster decision. I wanted to a look at this deal from every angle involved.
Milwaukee Bucks
The Bucks swooped in seemingly out of nowhere to win the Lillard sweepstakes. I almost didn’t believe it when I got the notification of the Woj tweet. If the Bucks weren’t all the way in before, they are now. They have no control over any first round picks through 2030, having had traded picks in 2025, 2027, 2029 and swaps in 2024, 2026, 2028, and 2030. I suspect they might have dealt Jrue Holiday at a high point in his value, as he is already 33 and looking for an extension. Bringing in Lillard would seem to be a clear upgrade offensively in the playoffs, an area where Holiday has struggled while in Milwaukee. Jrue’s defense will be missed, but being able to lean on arguably the best defensive frontcourt in the league in Giannis Antetokounmpo and Brook Lopez helps there. Lillard’s ability to take volume off the dribble, pull up threes from range at the guard position brings a dynamic to a Bucks offense that it hasn’t had before. The Khris Middleton/Giannis Antetokounmpo pick and roll has been deadly for Milwaukee over the years, so I can only imagine how much deadlier it will become replacing Middleton with Lillard.
Shipping out Grayson Allen as matching salary made the most sense, as he was set to be an unrestricted free agent after this year while Connaughton is under contract for longer. However, Allen did become a dead-eye three point shooter on good volume in Milwaukee while developing a chemistry with Giannis. The minimum signing of Malik Beasley could loom large here, but I would suspect Connaughton takes over in the starting lineup and they are looking for MarJon Beauchamp to take a leap forward in year two.
Dealing for Lillard implies that the Bucks are still committed to spending deep into the luxury tax over the long-term to compete for championships. Lillard has 4 years, ~$214 million (depends upon cap increases) remaining under contract, with a player option in the last year, 2026/2027. The team already has ~$185 million under contract for 2024/2025, though they could still stay under the second apron depending on how much the salary cap rises. Things could start to get very expensive in 2025/2026, with Antetokounmpo, Middleton, Connaughton and Bobby Portis all having player options, though the projected 10% max cap increase due to the new tv deal could help soften the luxury tax hit.
All in all, the Bucks seemingly made this move in response to Giannis’ recent comments about not re-signing in Milwaukee if everyone is not committed to winning championships. Oddly enough, it would seem those very same comments made the Bucks offer potentially more attractive to Portland, casting doubt on the fact that Giannis will be around when those picks come due. We will see if this deal ultimately puts the Bucks in a place where Antetokounmpo will sign an extension, but presumably any deal still won’t come until next summer. Regardless, its refreshing to see a small market team double down on their championship aspirations when called to action by their star player.
Portland Trail Blazers
The Blazers finally ripped the band-aid off. Without knowing the other offers that were made from other teams (though the assumption can be made that they obviously weren’t as attractive as the Milwaukee offer in Portland’s eyes), I think they did very well here. They took a gamble on quality over quantity when it comes to the lone first round pick in addition to the swaps they received, and will recoup even more draft assets once they re-route Jrue Holiday. Taking a gamble on Deandre Ayton and his contract is a pretty big decision, but at such a low price point they basically had to do it. Plus, Ayton’s max deal ends while both Shaedon Sharpe and Scoot Henderson are still on their rookie-scale contracts, so there is no impending cap crunch coming. However, I should note that they are only about $5 million from the luxury tax line this year with a couple roster spots to fill yet. Something to keep an eye on in any Holiday deal, as they can’t really take on much more money than they are sending out without bumping up into the luxury tax barrier. Speaking of a Jrue deal, I imagine almost every contender in the league will be expressing interest. Teams like Toronto, Miami, Boston, Golden State, Philadelphia, and the Clippers are sure to be the hot names in pursuit. But I could see teams like Indiana or Brooklyn sneaking their way into the discussion trying to make a splash, and they have the contracts/draft assets to make an attractive offer.
As Portland heads into a full-on rebuild, I’d imagine we will be hearing a lot of Jerami Grant trade rumors around the trade deadline. Grant’s new deal comes out as positive value per EPV, as we project to enter this rising cap environment. Additionally, he plays a position of premium value around the league. Teams may also inquire about the availability of Anfernee Simons, with the backcourt of the future set to be Henderson/Sharpe. With the Big Decision finally made in Portland, the team is set to sort through the fall-out for years to come. But between their Dame return / recent draft history, they have put themselves in a good place to begin their rebuild.
Phoenix Suns
It had been rumored that the Suns were set to serve as a third team in facilitating any Damian Lillard deal, landing Jusuf Nurkic with Ayton going to Portland. In the final iteration, they end up with Nurkic, Grayson Allen, Nassir Little, and Keon Johnson. It seemed Phoenix was determined to turn Ayton into some real depth for a team that didn’t have much. Also, they were able to break up his contract ($32.5 mil) into multiple chunky deals that can help facilitate future, smaller deals if needed (Nurkic $16.9/$18.1/$19.4, Little $6.3/$6.8/$7.3/$7.8, Allen $9.4). I would keep an eye on them re-routing Allen at some point this year, as he’s set to be an unrestricted free agent next summer and the team is already neck deep in the luxury tax for 2024/2025. The team actually took on more money in this deal for this season, adding around $5 million to their luxury tax bill.
From an on-court perspective, its hard to convince me that the team got better. Nurkic seems like a clear downgrade at the center position, and while the depth will help during the regular season, I don’t see any of those players being difference makers in the playoffs. It would seem the team sold at a low point in Ayton’s value as well. But we will see how it shakes out this season, and the team was able to shave off some money down the line that should help with the coming luxury tax bills.
Who’s Next?
With the Damian Lillard domino having fallen, who is next-up on the star trade docket? It would appear that Jrue Holiday is clearly the choice, with the Blazers indicating that they are looking to move him rather quickly. In fact, a Holiday deal could have pretty big ramifications for the lone disgruntled star with a trade request left, James Harden. Holiday is a more attractive trade target for teams and comes with none of the baggage. You will also have the opportunity to extend him, unlike Harden. Unless it can be worked into some three team trade that moves both Holiday and Harden to preferred destinations, this Damian Lillard deal has thrown yet another monkey wrench into the James Harden trade request fiasco.