Damian Lillard’s return to Portland is a great story, but also a questionable basketball move

We all thought the same thing when Damian Lillard agreed to return to the Portland Trail Blazers: “Oh, what a nice story!”

And, yes, it certainly is a nice story.

Lillard took his shot at trying to contend for a championship elsewhere, but it’s ultimately good for the sport when legendary players end their careers with their original teams. He can recover from his torn Achilles with a medical staff he knows and trusts, and more importantly, he can be near his family as he does so. Portland’s young players will benefit from the presence of a franchise icon and strong culture-setter. All of this is true. All of this makes sense. The vibes here are immaculate.

But vibes alone don’t win basketball games.

After all, the Blazers are still in the thick of a rebuild that was kicked off, coincidentally, by the 2023 Lillard trade. While they flashed some promise down the stretch last season, there’s obviously a ways to go before the Blazers can credibly consider themselves anything more than, say, a play-in contender. Exactly how Lillard fits into that rebuild is where the questions start to arise.

The financials

Let’s start with where he fits onto Portland’s balance sheet. The 2025-26 answer there is simple. Even if he doesn’t play, he slides very snuggly into Portland’s full mid-level exception. The Blazers essentially cleared the money to give him that exception without paying the luxury tax by buying out Deandre Ayton. Perhaps they could have used that exception on someone who could play for them this season, but worthwhile talent wasn’t really available two weeks into free agency, and even though they could have used it in a trade, this isn’t a team that really needed another $15 million player. They have plenty of depth. The question for them moving forward is star power.

Lillard obviously once provided quite a bit of it. Odds are, however, he won’t as a 36-year-old coming off of a torn Achilles tendon during the 2026-27 season. Coming into this offseason, there were scenarios in which Portland had max cap space going into the summer of 2026. Now, with Lillard and Jrue Holiday on their books, their only path to getting there would involve renouncing the cap holds on all of their free agents. Among those free agents is former No. 7 pick Shaedon Sharpe, who absolutely will not be renounced — so there goes Portland’s 2026 space, barring more moves.

Now think about the 2027-28 season. They already owed Holiday $37.2 million in what will be his age-37 season and Jerami Grant $36.4 million in what will be his age-33 season. Throw in Lillard at $14 million, and that’s over $87 million owed to three players who will at the very least be far beyond their prime. In the unlikely event that any of the three is outplaying those contracts when the time arrives, they all have player options and can opt out to squeeze Portland for more money.

That’s a strange place for an ostensibly rebuilding team to be, isn’t in? Especially since most of the significant young players on their roster will be earning market-rate money at that point. Defensive star Toumani Camara will be an unrestricted free agent in 2027. Sharpe will need to be paid either through a rookie extension this offseason or restricted free agency next offseason. Scoot Henderson is in the same boat, but a year later — meaning his next deal will kick in for the 2027-28 campaign, when Holiday, Grant and Lillard are all still making money.

Let’s talk about Sharpe and Henderson for a moment. One of the theoretical motivations for taking on Holiday’s long-term contract was getting Anfernee Simons off of the roster. The Blazers needed to clear starting spots for Henderson and Sharpe. While both have very impressive physical tools and have shown promise, neither has proven himself a true long-term cornerstone. This season, in large part, is going to be about finding out if one or both them can ultimately become one. Having Lillard in the building will probably help them.

Whose team will it be?

But what happens when Lillard gets healthy? In a world in which Henderson and/or Sharpe ultimately fails to secure a future in Portland, Lillard likely slides back into a starting role in 2026. But at that point, what are you really trying to do as a team? Win now around a version of Lillard that has likely taken a significant step back due to age and injury? There wouldn’t exactly be a road to tanking again with the roster in its anticipated condition. Would they just be buying time until those valuable Milwaukee picks gained in the 2023 trade come home to roost? The overall franchise outlook gets bleak if the keys to the offense are fully in Lillard’s hands when he comes back.

The preferable scenario here, obviously, would be breakout seasons for Henderson and Sharpe. But what would that mean for Lillard? Is he comfortable coming off of the bench? You never quite know with players of that stature. Even the 40-year-old Chris Paul still reportedly wants to start. Other Hall of Famers like Carmelo Anthony and Russell Westbrook needed to get dragged kicking and screaming onto the bench. 

The ideal model for Lillard here would likely be Dwyane Wade in his return to Miami. Across 93 games in his second Heat stint, he started only twice and averaged around 25 minutes. In theory, even a compromised version of Lillard could help the Blazers quite a bit in that position. This team badly needs shot-creation. Portland just ranked 22nd in offense last season and 26th in 3-point percentage. A smaller dose of Lillard could go a long way on that front, no matter what they get out of Sharpe and Henderson.

There’s no telling whether or not Lillard would accept such a role. Portland could feasibly start him with Sharpe and Henderson in a three-guard alignment, but that would compromise the defense-first identity they developed last season and deprive an essential youngster like Deni Avdija or Toumani Camara of a deserved starting slot.

All of this is before we consider the relatively similar position Holiday now finds himself in. He doesn’t have the same equity with the team that Lillard does, and he never quite reached the same heights as an individual player. But he’s a Hall of Fame candidate going from a starting role on a defending champion to an uncertain position on a team that hasn’t made the playoffs since 2021.

Would Portland have made the Holiday trade if it knew Lillard was coming? We’ll never know for sure. They are very different basketball players, but part of the appeal of having Holiday was his impact on culture as a revered teammate. Lillard theoretically checks that box at a substantially lower price. There’s nothing wrong with having multiple respected veterans, but it can cramp a rotation.

Another trade looming?

Does all of this mean Portland shouldn’t have signed Lillard? No, not necessarily. It’s a questionable move — not a bad one — that certainly raises important questions about how Portland plans to spend the next few years. The cost here, despite that iffy third-year player option, was low enough that it was probably a worthwhile swing. If nothing else the fans will love it, and there are quite a few scenarios in which this winds up making plenty of basketball sense.

If Lillard is re-signing with the idea that he will ease into a smaller role upon his return and then retire gracefully as a supporting player like Wade did, it’s an easy victory. If Portland has another move lined up to absorb Grant’s bad contract, the sting of that third Lillard season is lessened significantly. If Henderson and/or Sharpe do ultimately break out this season and credit Lillard for their ascent, that alone probably justifies the contract.

It’s also plausible that this was just a way for Lillard to get his money while he recovered from injury before eventually being rerouted to a championship contender of his choosing down the line, having used this gap year to make amends with the Blazers. There has been no reporting to that effect, but there’s a common-sense element to that possibility. He likely would have been forced to sign for the minimum if he’d gone to an immediate contender. Portland had the mid-level exception and wasn’t doing anything with it. He would likely generate meaningful trade interest at mid-level money once he’s healthy, so the Blazers could do Lillard a solid by getting him to his desired location on a bigger contract and even get an asset back for their troubles.

The only thing Hall of Famers hate more than moving to the bench is taking minimum-salary contracts, after all. Given the no-trade clause Lillard secured in this deal and the acrimony surrounding his 2023 trade request, another departure from Portland would only come up if Lillard so desired, but it would be hard to rule out entirely given everything we’ve covered.

So as reasonable as that heartwarming first thought was, your second thought following Lillard’s reunion with the Blazers probably related to the many, many basketball questions the move raised. He and the Blazers may be able to provide entirely satisfactory answers in the years to come, but all of those questions are lingering as Portland attempts to climb from plucky second-half underdog story to a legitimate playoff team and beyond.