The Portland Trail Blazers emerged out of left field as one of the top options for Damian Lillard, with the two sides soon agreeing to a three-year, $45 million deal. People assumed that Dame would go to a team like the Celtics, where he'd have a shot to win a title, but the pull to return to Portland was too much for him to ignore.
In a way, the move makes sense for Lillard, who never acclimated to Milwaukee. He's back in his NBA home, much closer to his real home in California. However, it's tough to envision Portland as a contender in the 2026-27 season, when Lillard returns. The move is questionable from both sides, especially from the organization's perspective.
Lillard joins Jerami Grant and Jrue Holiday as veterans on an otherwise young roster. Lillard will make $14.1 million next season, Grant will make $32 million, and Holiday will make a team-high $32.4 million. They make up three of the four highest-paid players on the roster, with Deni Avdija making $14.4 million next season.
The trio of Dame, Jerami, and Jrue will take up more than half of the team's cap space in 2025-26 and 2026-27. That trend could carry over into the 2027-28 season if Lillard picks up his $14.1 million player option, and Grant does the same with his $36.4 million option. The Trail Blazers aren't facing financial constraints now, but they will run into issues in the future.
Blazers are committed to paying big money to veterans like Dame
Portland trading for Holiday (again) and signing Lillard this summer doesn't add up, not when you have younger players who will be due (or are already due) for paydays over the next couple of years.
Shaedon Sharpe, Toumani Camara, and Rayan Rupert are extension eligible. Scoot Henderson will be extension-eligible next summer. You can't forget about Avdija, who had a breakout season in 2024-25. If he continues to play like he has, the Trail Blazers will want to lock him down to a new deal in a couple of years.
If you're trying to see the meaning behind Portland's offseason decisions thus far, good luck. There is no pattern. The Trail Blazers are still finding ways to commit big money to veteran players, while trying to determine which players from their young core are worth keeping. It'd be different if Portland were built to contend as currently constructed, but that isn't the case.
There are reasons for fans to be optimistic about the future, but there are even more reasons to be confused. It's a weird balance. Good luck to the front office in figuring out their own decisions.