Damian Lillard went to bed on Monday night trapped on a sinking ship. He was a member of a Milwaukee Bucks team desperately trying to reshape its roster to appease Antetokounmpo without him, as Lillard will presumably miss most or all of the 2025-26 season recovering from a torn Achilles tendon. In the best-case scenario, he and Antetokounmpo would be fighting an uphill battle to contend upon his eventual return. Worst-case, Antetokounmpo would jump overboard and leave Lillard, on a giant contract, to languish on a team he never really wanted to play for.
But Milwaukee’s stunning acquisition of Myles Turner gave Lillard a reprieve. He is now a free agent capable of picking not only where he plays next, but when. He’s getting paid for the next two years either way. If he wants to sit out and recover, he can do so. If he wants to see how the year plays out and potentially join a contender in the middle of the season, that’s an option as well. Literally any team with a roster spot is a plausible option. Whatever he signs for over the next two years is just offset by what Milwaukee owes him, so he has no reason to ask for anything more than the minimum.
So with all of that in mind… where should Lillard head next? We’re looking mostly at contenders here. Ideally, they wouldn’t have to rely on him as a full-time starter in the next two years, but they should have a meaty role available for him if he proves capable of filling it after his injury. Here are five teams to keep in mind.
No, Portland probably isn’t the permanent destination if Lillard plans to contend. However, a very brief, year-long pit stop back at his old stomping grounds actually makes a lot of sense for Lillard. His family is in Portland. That’s likely where he would prefer to rehab from his torn Achilles. If he signs a one-year, minimum-salary contract in Portland, he could do it under the supervision of a team medical staff he likely knows and trusts from his time with the Blazers. The two sides could even agree as part of the deal that if Lillard looks ready to play by mid-season, the Blazers would waive him and let him join a contender immediately.
So, why would Portland do this? Well, to mend fences, for one. Few players are more beloved by a single fanbase than Lillard is by Portland’s. Their 2023 breakup was somewhat acrimonious, so potentially repairing the relationship with a franchise icon would be nice. However, we should also note that Portland just traded for a 35-year-old Jrue Holiday ostensibly in part to mentor young guards Scoot Henderson and Shaedon Sharpe. Well, if that’s a priority in Portland, wouldn’t having Lillard in the building as he recovers be beneficial for them as well? Even if he never plays another game as a Blazer, Portland could intangibly benefit from his presence.
As of right now, the Blazers are around $18 million below the luxury-tax line with two roster spots open after buying out Deandre Ayton. That’s more than enough money for them to use the full non-taxpayer mid-level exception on someone they actually plan to use and still retain enough to sign Lillard for the minimum without becoming a tax team. Maybe Lillard doesn’t want to attach himself to a team yet, but if he’s going to recover in Portland anyway, this could make some sense for both sides.
We probably have to acknowledge Miami as a suitor here just given how badly Lillard wanted to join the Heat in 2023. Miami is reportedly going to be interested this time around as well, according to the AP’s Tim Reynolds. Given Miami’s general track record when it comes to health and conditioning, it would be a pretty good place to rehab a major injury. However, a lot has changed since 2023.
For starters, Jimmy Butler is no longer on the team. When Lillard wanted to go to Miami back then, he was expecting to join a reigning Eastern Conference champion with Butler and Bam Adebayo. Now Butler is gone and Andrew Wiggins is in his place. Meanwhile, Tyler Herro, who almost certainly would have been in Lillard trade two summers ago, was just an All-Star. He and Lillard, especially post-Achilles Lillard, would not be a defensively viable starting backcourt, but it’s hard to imagine the Heat trading Herro elsewhere for defense to facilitate such a high-risk addition.
So the Heat are in the mix, of course. They almost always are for players of this stature. But it’s not the slam dunk it would have been two years ago. At this point, Lillard can probably find better fits elsewhere.
Let’s say money and fit are not an issue for a moment. Your sole goal is to win a championship in the next several years. Where would you want to be? The obvious answer would be “on the Oklahoma City Thunder,” but they have a full roster and likely see no great need to bring in a high-risk veteran. Your next choice would be “Victor Wembanyama’s team,” but the Spurs already have a guard glut with De’Aaron Fox, Dylan Harper and Stephon Castle. So where would you go after that? Your two best bets are “Nikola Jokić’s team” and “the Eastern Conference.”
Let’s table the East for a moment (we’ll get back to it!) and focus on Jokić. No, Lillard would not start in Denver. Jamal Murray is entrenched at point guard and they need Christian Braun’s defense next to him. However, what they showed with Russell Westbrook last season was a willingness to give major minutes to and even close some games with a backup point guard on the floor. The same situation could apply to Lillard. He’d join the team with a baseline of 15 or 20 minutes guaranteed per game, but when he’s playing well or matchups dictate it, he could easily play more. Given Murray’s injury history, having a backup capable of starting and delivering in a high-usage role means quite a bit for the Nuggets.
If your goal is to win a title, playing with the best player in the world makes a lot of sense. Denver took a meaningful step forward by swapping Michael Porter Jr. for Cam Johnson on Monday, but bringing in Lillard would give them enough upside to really threaten Oklahoma City in the playoffs. They took the Thunder to seven last year despite barely having any supporting offense. Lillard would obviously have a chance to fix that if healthy, whether that’s this year or next.
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See, I told you we’d circle back to the East. Realistically, you could toss any Eastern Conference contender into the mix here. The Knicks just signed Jordan Clarkson to be their bench scorer. He could keep Lillard’s seat warm while he recovers. The Magic have needed a point guard and a perimeter scoring threat for years. They addressed both needs this offseason with Desmond Bane and Tyus Jones. Why not double down and nab Lillard for the minimum if he’s interested? Boston just gave up Holiday. Maybe Lillard and Jayson Tatum could rehabilitate their Achilles tears together and try to take the league by storm as teammates in 2026.
These are all somewhat viable options, but Cleveland, the conference favorite, stands out. The Cavaliers just lost Sixth Man of the Year candidate Ty Jerome to the Grizzlies in free agency because he got too expensive. You know who isn’t going to be expensive? Lillard. You know who would thrive in a 20-minute “just go get a bunch of buckets and space the floor” role? Lillard. You know who spent his entire career waiting to play with the sort of size, wing depth and scoring help the Cavaliers have to offer? Lillard.
Cleveland did just trade for Lonzo Ball, but he’s more of a transition point guard than a half-court point guard. He can defend pretty much any guard, so there’s not much overlap there. Cleveland probably wouldn’t want too many minutes with both Lillard and Darius Garland on the floor given their size and defensive limitations, but that’s a solvable problem. Cleveland has no other path to this level of talent with only the minimum to spend, so it would be a very worthy gamble for them if Lillard were interested.
Is there a contender out there who would obviously have a starting job available for Lillard? Minnesota makes the most sense on that front. Mike Conley is still here, but he’s 37 and declining. Rob Dillingham and Terrence Shannon are both in the building as possible long-term replacements, but neither are ready to start yet and neither are ideally suited to play point guard either. Whenever Lillard is ultimately healthy, be that at the end of this year or the beginning of next, Minnesota would likely be positioned to guarantee him a starting job. If that’s a priority, the Timberwolves have an advantage.
The fit in Minnesota would be relatively seamless. Anthony Edwards is the primary scorer, so Lillard could ease back into a higher-usage role with time. Edwards and Jaden McDaniels are such strong perimeter defenders that Lillard could hide on the easiest possible matchup. Rudy Gobert can cover up his mistakes at the rim, and there’s plenty of depth here in case he’s never quite up to a typical starter’s minutes load again. Rarely do stars want to live in Minnesota, but hey, Lillard was happy in Portland for years, so maybe he’s the exception.
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