Damian Lillard is going back to the place he never wanted to leave.
Lillard has agreed to the three-year, $42 million deal with the Portland Trail Blazers in free agency, according to insider Shams Charania. The 35-year-old guard will be out all of next season as he rehabs a torn Achilles suffered during the 2025 NBA Playoffs. Lillard became a free agent in shocking fashion when the Milwaukee Bucks waived-and-stretched his contract to sign Myles Turner at the start of free agency.
Lillard was named an All-Star this past season before the injury by averaging 24.9 points, 7.1 assists, and 4.7 rebounds per game on 62 percent true shooting and 37.6 percent three-point shooting on nine attempts per game. Those are phenomenal numbers for a smaller, aging guard, but the reality is the Bucks’ Lillard experiment was a monumental bust that resulted in zero playoff series wins.
Lillard had “multiple mid-level exception and minimum offers from NBA contenders,” according to Charania, but chose to go back to Portland instead. Dame has a case as the Greatest Blazer of All-Time, and now he’ll get to finish his career with the team that drafted him. Lillard is also getting a no-trade clause in the deal.
Let’s grade Lillard’s decision to sign with Portland for the player and the team.
Damian Lillard grade for signing with Trail Blazers
The grass isn’t always greener. Lillard learned that lesson when he was traded from Portland to Milwaukee, where he spent two frustrating years failing to build the necessary chemistry with Antetokounmpo. What seemed like a wonderfully complementary pairing on paper never really worked out for a variety of reasons, from coaching styles to a decaying supporting cast to injuries.
It’s easy to imagine that Lillard was stunned to learn the Bucks waived him earlier this month, but it worked out incredibly well for him. He gets the full $113 million salary he was owed from Milwaukee for the next two years while the team spreads the cap hit over five years. The release also gave Dame the freedom to choose where he wanted to finish his career, which had to be deeply satisfying after his original trade fiasco in Portland. Lillard reportedly had his heart set on playing for the Miami Heat coming off their 2023 NBA Finals run, but the Bucks offered the best package, and Lillard had no choice but to make the best of it.
How much will Dame have left in the tank when he comes back? An Achilles tear is perhaps the hardest ‘common’ injury to return from in the NBA, and that’s especially the case the later you get in your career. Kobe Bryant tore his Achilles at 34 years old and was never the same again. Lillard is smaller and worse defensively. His pull-up shooting and pick-and-roll playmaking should still have some utility, but it’s hard to be too optimistic about the level he’ll return at.
Lillard could have chased a ring elsewhere to close his career, but he chose to go back to the city he considers home. It would be fascinating to see the other offers and get a look at which teams really wanted him on the brink of a lost season rehabbing a terrible injury. The bar for a successful Blazers return will be fairly manageable: he’ll have to mentor young guards like Scoot Henderson and Shaedon Sharpe, be an ambassador for the organization, and try to get Portland back into the playoffs after a long drought.
The Blazers have the ideal defensive infrastructure to cover Lillard on that end. Portland can put a team of huge defenders around him at every other position and let him carry the offense, if he’s still capable of doing that post-injury. The fit on paper makes sense, but there are a lot of ifs.
Lillard is also getting paid a ton of money. He’ll be making around $70 million next season without playing a game. That’s great work if you can get it. I think this is a wonderful story for a beloved star player who means so much more to Portland than he would anywhere else. Lillard’s days as an elite player are likely over, but if he hits one clutch shot in a big situation again in a Blazers uniform, the storybook ending will have written itself.
Grade: A
Trail Blazers grade for signing Damian Lillard
It’s easy to understand why the Blazers wanted to bring back Lillard on the surface: he’s a franchise legend, and they want to do right by him before he retires. I just wonder how Lillard fits into the big picture of Portland’s rebuild.
The Blazers are seemingly trying to accelerate their timeline for a playoff push. Portland made a surprising decision to acquire Jrue Holiday via trade from the Boston Celtics this offseason despite him showing signs of aging last season. Now 35 years old, Holiday can still be an effective defender and leader, but he doesn’t have quite as much scoring punch as he used to, and he’s on a huge contract for three more years. There were whispers that Holiday initially wasn’t thrilled to land in Portland, but getting Lillard back in town will make him feel more comfortable.
The Blazers brought in Holiday to fortify their defense and add a veteran presence to their young core. Portland has some nice pieces in place and is starting to form a real defensive identity. Donovan Clingan, Toumani Camara, and Deni Avdija is a very good young, defensive-minded front court to build around. Portland needs young guards Scoot Henderson and Shaedon Sharpe to take a leap. Ultimately, Sharpe and Henderson will determine where this franchise is going for the rest of the decade.
I wonder how Henderson and Sharpe will feel about Lillard’s return. If Henderson struggles to take a step forward this season and Lillard comes back looking like himself a year from now, will be the Blazers be ready to give Dame starting and/or closing minutes over the youngster? Will Lillard be happy sitting at the end of games if he feels like he’s still better than the younger guards on the team?
I find this to be kind of an odd decision by Portland. Just when they were stating to turn the corner on their rebuild, they are now leaning back to their past to appease a franchise legend. There’s a chance this works out really well for both parties, but I worry there’s some downside for the Blazers.
Portland got a really good deal in return for Lillard. They own the Bucks’ unprotected 2029 first round pick, and two swaps. In that sense, Portland still has plenty of outs to build a good team, but it does feel like the front office could be on the hot seat if the roster doesn’t take a step forward this year. This is a reasonable salary for Lillard, and the no-trade clause won’t be as difficult to work around as it was for the Suns with Bradley Beal.
The Blazers have an uphill climb and little margin for error in the West if they want to make the postseason. They don’t have a star player, and they are saddled with Jerami Grant’s huge contract for several more seasons that they seemingly can’t give away. It doesn’t feel like this Portland rebuild is anything close to finished product, which is why adding Dame feels a bit odd. It’s a nice story, but I’m skeptical this is the right move for the Blazers.
Grade: C+
