As of Monday night, Damian Lillard was in an extremely uncertain situation with the Milwaukee Bucks. The team was trying to rebuild the roster to keep Giannis Antetokounmpo, while Lillard himself would presumably miss most or all of the 2025-26 season due to a torn Achilles tendon. In the best case, upon his return, he and Antetokounmpo would have to fight for contender status. In the worst case, Giannis would leave the team, leaving Lillard with a huge contract on a club he never truly wanted to play for.
However, Milwaukee`s unexpected acquisition of Myles Turner gave Lillard a reprieve. He is now a free agent and can choose not only where to play next, but also when. He will be paid for the next two years either way. If he wants to take a break and recover, he can do so. If he wants to see how the season unfolds and potentially join a contender in the middle of the season, that is also possible. Literally any team with a free roster spot is a potential option. His salary for the next two years will be offset by what Milwaukee owes him, so he has no reason to ask for more than the minimum.
Given all of this… where should Lillard go next? We are mainly looking at contender teams. Ideally, they shouldn`t rely on him as a full-time starter in the next two years, but they should have the opportunity to give him a significant role if he shows he is capable of performing it after the injury. Here are five teams worth considering.
1. Portland Trail Blazers
No, Portland is likely not the final destination if Lillard plans to compete for a title. However, a very short, year-long stop back at his old place makes a lot of sense for Damian. His family lives in Portland. He would likely prefer to recover there after tearing his Achilles. If he signs a one-year, minimum-salary contract in Portland, he could do so under the supervision of the team`s medical staff, whom he likely trusts from his time with the Blazers. The sides could even agree that if Lillard is ready to play by mid-season, the Blazers would waive him so he could immediately join a title contender.
So why would Portland do this? First, to mend fences. Few players are as loved by fans as Lillard is in Portland. Their separation in 2023 was quite strained, so restoring relations with a franchise icon would be a nice step. However, it`s worth noting that Portland just traded for 35-year-old Jrue Holiday, presumably partly so he could mentor young guards Scoot Henderson and Shaedon Sharpe. If that`s a priority for Portland, wouldn`t having Lillard in the building during his recovery be beneficial for them too? Even if he never plays another game for the Blazers, his presence could bring intangible benefits to the team.
Currently, the Blazers are about $18 million below the luxury tax threshold, with two roster spots open after buying out Deandre Ayton`s contract. This is more than enough to use the full non-taxpayer mid-level exception on a player they actually plan to use, while still having enough left to sign Lillard for the minimum without becoming a tax-paying team. Perhaps Lillard doesn`t want to commit to any team yet, but if he`s going to recover in Portland anyway, this could make sense for both sides.
2. Miami Heat
We probably have to mention Miami as a potential suitor, given how much Lillard wanted to join the Heat in 2023. Miami is reportedly interested this time as well, according to Tim Reynolds of the AP. Given Miami`s general reputation regarding health and conditioning, it would be a good place to recover from a serious injury. However, a lot has changed since 2023.
First, Jimmy Butler is no longer on the team. When Lillard wanted to go to Miami back then, he expected to join the reigning Eastern Conference champion with Butler and Bam Adebayo. Now Butler is gone, and Andrew Wiggins has taken his place. Meanwhile, Tyler Herro, who almost certainly would have been part of a Lillard trade two years ago, just became an All-Star. He and Lillard, especially Lillard after the Achilles injury, would not form a defensively reliable starting backcourt. It`s hard to imagine the Heat trading Herro for a defensive player just to facilitate such a risky acquisition.
So, the Heat are, of course, on the list of possible options. They almost always are when it comes to players of this stature. But it`s not as clear-cut a decision as it was two years ago. At this point, Lillard can probably find better options elsewhere.
3. Denver Nuggets
Let`s say, for a moment, that money and fit don`t matter. Your sole goal is to win a championship in the next few years. Where would you want to be? The obvious answer is on the Oklahoma City Thunder, but they have a full roster and likely see no great need for a high-risk veteran. Your next choice is “Victor Wembanyama`s team,” but the Spurs already have a guard glut in De`Aaron Fox, Dylan Harper, and Stephon Castle. So where would you go after that? Your two best options 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 firmly 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 significant minutes and even finish some games with a backup point guard on the floor. The same situation could apply to Lillard. He would join the team with a guaranteed 15 or 20 minutes per game, but when he plays well or matchups dictate it, he could easily play more. Given Murray`s injury history, having a backup capable of starting and performing effectively in a high-usage role means a lot to the Nuggets.
If your goal is to win a title, playing with the best player in the world makes a lot of sense. Denver made a significant step forward by swapping Michael Porter Jr. for Cam Johnson on Monday, but bringing in Lillard would give them enough upside to truly threaten Oklahoma City in the playoffs. Last year, they pushed the series with the Thunder to seven games despite virtually no supporting offense. Lillard would obviously have a chance to fix that if healthy, whether this year or next.
4. Cleveland Cavaliers
See, I told you we`d circle back to the East. Realistically, you could add any Eastern Conference contender here. The Knicks just signed Jordan Clarkson as their bench scorer. He could “warm the seat” for Lillard while he recovers. The Magic have needed a point guard and an outside threat for years. They addressed both issues this offseason by acquiring Desmond Bane and Tyus Jones. Why not double down and get Lillard for the minimum if he`s interested? Boston just traded Holiday. Perhaps Lillard and Jayson Tatum can recover together from their Achilles injuries and try to “explode” the league as teammates in 2026.
All of these are somewhat viable options, but Cleveland, the conference favorite, stands out. The Cavaliers just lost Sixth Man of the Year candidate Ty Jerome, who went to the Grizzlies because he became too expensive. You know who won`t be expensive? Lillard. You know who would excel in a “just go get a bunch of buckets and space the floor” role for 20 minutes per game? Lillard. You know who spent his entire career waiting for the opportunity to play with the size, wing depth, and offensive help that the Cavaliers offer? Lillard.
Cleveland did just trade for Lonzo Ball, but he`s more of a transition point guard than a half-court one. He can defend virtually any guard, so there`s not much overlap here. Cleveland probably wouldn`t want to spend too many minutes with both Lillard and Darius Garland on the floor due to their small size and defensive limitations, but that`s a solvable problem. Cleveland has no other way to acquire a player of this talent level with only a minimum salary to spend, so it would be a very worthwhile gamble for them if Lillard were interested.
5. Minnesota Timberwolves
Is there a contender out there where a starting spot would be obvious for Lillard? Minnesota makes the most sense in this regard. Mike Conley is still here, but he`s 37 and declining. Rob Dillingham and Terrence Shannon are both on the team as potential long-term replacements, but neither is ready to start yet, and neither is ideally suited for the point guard role. Whenever Lillard recovers, be it at the end of this year or the beginning of next, Minnesota will likely be able to guarantee him a starting spot. If that`s a priority for the player, the Timberwolves have an advantage.
The fit in Minnesota would be relatively seamless. Anthony Edwards is the primary scorer, so Lillard could gradually return to a role with higher usage. Edwards and Jaden McDaniels are so strong in perimeter defense that Lillard could “hide” on the easiest opponent. Rudy Gobert can cover his mistakes near the rim, and there is enough roster depth in case he can never fully handle a typical starter`s workload. Rarely do stars want to live in Minnesota, but hey, Lillard was happy in Portland for years, so maybe he`s the exception.
Jasper Hawthorne