In an exciting turn of events, Damian Lillard has reunited with the Portland Trail Blazers, signing a three-year, $42 million deal. Lillard gets the opportunity to finish his career in Portland, strengthening his case to go down as the best Blazer to ever do it. Most importantly for Lillard, he gets to be close to his family in Portland as he continues to rehab from a torn Achilles.
It's likely that Dame's brutal injury keeps him out for the entirety of the 2025-26 season. Despite this, the Blazers' next move should be to trade Jrue Holiday (again).
Damian Lillard signing gifts Blazers get-out-of-jail-free card
Between Holiday, Lillard, and the up-and-coming Scoot Henderson, Portland's backcourt is crowded yet again. They need to resolve this logjam, and it makes little sense for a rebuilding Blazers team to have two aging star guards on their roster, given how far away they are from becoming contenders.
Although we didn't agree with general manager Joe Cronin's decision to acquire Holiday, we also see the vision. Portland is leaning into its defensive identity and adding someone who has a league-wide reputation for being a great teammate. Holiday's low usage rate (16.6) and veteran presence are an investment in Henderson, who is poised for a breakout season.
However, Holiday's age (35), declining production (11.1 points, 3.9 assists), and the injury concerns that forced Portland to revise their original trade have made his three-year, $104 million contract into one of the worst deals in the league.
The Blazers didn't know that Lillard was going to be available at the time of their trade with Boston, and, in retrospect, never should've made that deal. In Lillard, they found a cheaper, more talented option.
While Lillard hinders Portland's defensive identity, they also desperately needed more shooting, playmaking, and overall offensive firepower. Last season with the Bucks, he averaged 24.9 points, 7.1 assists, and 4.7 rebounds on 45/38/92 shooting splits.
Shooting is typically the last thing to go for an aging player, giving us optimism that Lillard will remain impactful coming back from injury. His high volume and overall threat from beyond the arc are going to do wonders for the development of Portland's young core, opening up more driving lanes for Henderson, Shaedon Sharpe, and Deni Avdija.
Meanwhile, the pieces they got back from trading Lillard in the first place are still around, and just so happen to perfectly complement his strengths and weaknesses. Portland needs to move forward with a Scoot-Dame backcourt pairing, making Holiday the odd man out.