Winners and Losers from Damian Lillard’s Shocking $42M Return to the Blazers
It's never too late to return home. Damian Lillard just proved as much.
In a development that's just as stunning as it is feel-good, the 35-year-old star is heading back to the Portland Trail Blazers on a three-year, $42 million deal that includes a 2027-28 player option and a no-trade clause, according to ESPN's Shams Charania. Lillard plans to rehab his torn left Achilles for the entire 2025-26 season before returning to the court in 2026-27.
There is a lot to parse here. What does this say about the Blazers' rebuild? Didn't they just (re-)trade for Jrue Holiday? And, uh, what about Scoot Henderson, the prospect whose arrival basically drove Dame out of town? Why didn't Lillard ultimately land with a contender?
Let's pore over the move and deal with the fallout from this hopeless romantic's fever dream in one of the best ways we know how: By analyzing the full scope of winners and losers.
Winner: Damian Lillard
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Lillard is getting a big-time win here after a handful of gargantuan losses.
First, he suffered a career-altering Achilles injury shortly after returning from a blood clot. Then, the Milwaukee Bucks waived-and-stretched the remaining two years and $112.6 million on his contract, leaving him without an NBA home base.
Skip ahead a couple of weeks, and Lillard is now returning to the franchise where his career began, while having secured absolute control over his own future with a no-trade clause, on top of more money than he would have made over the next two seasons had the Bucks never sent him packing.
This is a monster victory before even factoring in the off-court implications. Lillard is an icon in Portland. He will be treated like royalty under the circumstances of his return. He will also get to rehab closer to his children, which ESPN's Shams Charania noted became a top priority for him.
Go ahead and search for the downside here if you're so inclined. There isn't any—not for Dame, anyway.
Loser: NBA Contenders Wanting Damian Lillard on the Cheap
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Plenty of people assumed Lillard would latch onto a contender, even if he didn't put pen to paper until the middle of season.
The scenario would be something like this: Lillard signs a one-plus-one on the cheap with Milwaukee already paying out his contract, returns to the floor in time for the 2026 playoffs or to start the 2026-27 campaign and then signs a larger contract during the 2027 offseason after having established Early Bird rights with his next squad.
Sure, the back-to-Portland storybook hypothetical was always floating around the ether. Emotional components and whatnot. But Jayson Tatum, as one example, was recruiting Lillard on behalf of the Boston Celtics, according to The Boston Globe's Gary Washburn.
Landing in Beantown, specifically, seemingly made too much sense. The Celtics are navigating a one-year break in contention with Tatum rehabbing his own torn right Achilles. The duo could have recovered together, returned to the floor in 2026-27 and resumed title pursuits. Boston, meanwhile, would have replaced some of the rotation punch it has surrendered—and may continue to shed—in the face of rising operating costs without having to break the bank.
That's not happening now. Not for the Celtics. Not for any other contender.
Winner: The Milwaukee Bucks'...Wallet
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Milwaukee will now have a portion of the nearly $113 million it owed Lillard offset by his new deal.
As ESPN's salary-cap guru Bobby Marks noted, the offset only applies to the original length of his contract—so, the next two years. It also doesn't get applied to the cap sheet until after the season.
Still, the Bucks wind up saving close to $11.7 million overall, bringing Lillard's dead cap hit from $22.5 million per year through 2029-30 down to around $20.2 million.
Hooray(?)!
Loser: Scoot Henderson
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The reunion between the Blazers and Lillard does not mean the team is giving up on Scoot Henderson. A lot can happen between now and the 2026-27 season.
This nevertheless adds an additional layer of pressure to the 2023 No. 3 overall pick entering his third year. He will now head into next summer eligible for an extension, with the return of a franchise icon looming over his head...and negotiations.
Speculation will run all sorts of rampant if Henderson doesn't progress by even larger margins than he did last year, when he looked far more in command of the offense and his spot within it. And this says nothing of the pressure he was already under.
Portland acquiring the uber-expensive Jrue Holiday prior to the draft is hardly a ringing endorsement for the 21-year-old. The two can play together, but Henderson has already spent the majority of his career coming off the bench. His path to taking the reins as the perma-starter is murkier.
Are we to believe the plan is for Holiday and/or Lillard to come off the by bench behind him in 2026-27?
Winner: Yang Hansen and Donovan Clingan
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I mean:
More seriously, the Blazers struggled to put their big men in advantageous positions last season. This won't help Yang Hansen (who may not need it, to be honest) or Donovan Clingan next season. But Lillard's return in 2026-27 ensures they'll have someone with the gravity to give them extra space in the middle of the floor and who makes more versatile passing reads than anyone else currently on the roster.
This won't be as much of a victory if Henderson pops in Year 3, Deni Avdija continues to progress and/or Portland adds another playmaker between now and the 2026-27 campaign. But any way the Blazers can streamline the offensive existence of their (two primary) bigs in the seasons to come matters.
Other Winners, Losers and TBDs
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To Be Determined: Shaedon Sharpe
Sharpe is eligible for his rookie-scale extension right now, and a lot of the murkiness that applies to Henderson's future is also relevant for him. The 22-year-old is more of an intuitive fit next to Lillard since he's not a point guard, but the Blazers once again have a backcourt logjam with those two, Henderson and Jrue Holiday.
Winner...and Loser(?): Jrue Holiday
Speaking of Holiday, he feels like a lock to get traded prior to 2026-27 with Lillard now back in the fold. Perhaps he'll be happy for a chance to play elsewhere. Maybe he'll be bummed about getting moved again—particularly if it happens midseason. Or maybe it turns out the Blazers can't find a taker for the balance of the 35-year-old's contract (three seasons, $104.4 million), and he'll either be elated or frustrated to stay put.
Winner: 2026-27 Rebuilding Squads
Just in case anyone wasn't sure whether the Blazers were fast-tracking their rebuild with the acquisition of Holiday, we now know they plan to hit the turbo button no later than next summer. That's fantastic news for any franchise looking to tank with minimal impediments.
Loser: 2025 Free Agents Still Looking for Leverage
The Blazers were unlikely to shell out this money for anyone other than Dame, but actually spending it removes them from the running for any free agents left on the board. If any of the remaining RFAs are getting ultra-squeezed (like Quentin Grimes and Cam Thomas) and were perhaps hoping Portland would dangle a mid-level offer sheet, that ship has officially sailed.
Dan Favale is a National NBA Writer for Bleacher Report. Follow him on Bluesky (@danfavale), and subscribe to the Hardwood Knocks podcast, co-hosted by Bleacher Report's Grant Hughes.
