How Does Damian Lillard Fit Into This Version Of The Trail Blazers

After a two-year voyage to the most diary-populated portion of the Midwest, Damian Lillard is back with the Portland Trail Blazers.

For over a decade, Lillard served as the undisputed face of the franchise. But a lot has changed since then. The Blazers now have a small militia of talented young players (headlined by Deni Avdija) who hope to usher the team into their next great era of basketball.

Lillard can no longer steer the ship. Rather, he has to find a way to amplify this young group. But how will Lillard fit in this time around?

Evaluating Damian Lillard’s Contract

As the tweet above states, Lillard agreed to a three-year, $42 million deal with the Blazers. The final year of that deal includes a player option.

Last season, Lillard’s production value was at 30.6 million dollars. If Lillard played that way when he returns in 2026-27, he’d be worth 36 million dollars that year because of the cap increase. Of course, Lillard will be 36 at that point and coming off a catastrophic injury. Therefore, it is doubtful that he’ll reach the level he was at in 2024-25. Still, if Lillard only plays half as well (production value of 18 million) as he did last year, he’d be outperforming his salary for 2026-27 (13.4 million, per Spotrac).

This doesn’t account for the 14.1 million that Portland will be paying Lillard to rehab. However, he can make up for that with the invaluable wisdom he is sure to impart to their young core. Besides, even after signing Lillard, the Blazers are still well below the dreaded first apron, so there is no real harm done by paying him right now.

Lillard’s deal also matches well with when Avdija and Donovan Clingan will be up for new contracts.

Lillard’s On-Court Fit With The Blazers

Despite the Milwaukee Bucks failing to live up to expectations after the trade, Lillard was pretty damn good. Last season, he averaged 24.8 points per 75 possessions (94th percentile) on 62.8% true shooting (87th percentile). Overall, he was in the 98th percentile in Offensive Estimated Plus-Minus (per Dunks & Threes).

With their stout cast of defenders (they were 6th in Defensive Rating after January 1), Portland should be able to hide Lillard’s limitations on that side of the court in a way the Bucks never could.

But, as we said, that was pre-Achilles tear Lillard. How good is post-Achilles tear Lillard on the offensive end? Is that version of him good enough to start over Scoot Henderson in what will be his fourth year at that point?

That’s the other part of this equation that is hard to forecast. The Blazers still have Henderson and Shaedon Sharpe. Plus, they added Jrue Holiday in a trade a few weeks before this signing.*

(*Sidebar: It’s pretty tragic that Lillard finally gets the perfect backcourt running mate in Portland in Holiday, and both of them are now old and out of their primes. The Basketball Gods can never give this man a break.)

Ideally, I’m sure the Blazers’ front office would like for Henderson and Sharpe to be good enough to be their starting backcourt in 2026-27. If that’s the case, would Lillard be willing to settle into a spark plug role off the bench? And on the flip side, if one (or both) of them flames out, will Lillard still have enough in the tank to help Portland overcome that hurdle?

There’s also the Avdija of all this. Last season, Avdija went from cult figure to a legitimate top 50 player in the sport. A big reason for this leap is that the Trail Blazers put the ball in his hands more and let him create for himself and teammates, leading to a career-high in unassisted field goal rate, true shooting, and points per game. Lillard is one of the most ball-dominant players in recent memory. Will he be able to scale back his usage to help guys like Avdija continue to flourish?

By all accounts, Lillard is a tireless worker and the ultimate teammate. There isn’t a doubt in my mind that he will do all he can to help the Blazers over the next three years. But still, it is hard not to ponder over all the interesting questions this reunion creates.