The Portland Trail Blazers signed Damian Lillard to a three-year, $42 million deal, which should be considered extremely team-friendly if he can return close to the same player he was prior to his brutal Achilles injury. But with Lillard now back in Portland, it makes it even harder to justify the puzzling Jrue Holiday trade.
Portland's revised trade with the Boston Celtics was a straight one-for-one swap for Anfernee Simons. Even with the Blazers getting their second-round picks back, this deal seems like a significant loss for them.
Damian Lillard signing makes Jrue Holiday a costly redundancy
Although we disagreed with the deal in the first place, the idea of trading for Holiday was that he's going to be a great veteran presence, providing Portland with an aging star guard to help them achieve two primary goals: ending a four-year postseason drought and furthering the development of their young core.
However, the Blazers just addressed the exact same things by signing Lillard. Both veteran guards bring value to a rebuilding team, but they also play redundant roles, making it inefficient to keep both on the roster.
Sure, having both Lillard and Holiday around is better than just one to achieve these goals, but is that luxury really worth paying Holiday $104 million over the next three years?
As someone who has already emerged as a superstar in Portland, Lillard is arguably even a better mentor for Scoot Henderson than Holiday. Perhaps most importantly, he's likely out for the entire 2025-26 season, giving Henderson a significantly increased role and opportunity to prove himself worthy of having the keys to the backcourt.
The Blazers must flip Holiday (again)
I'd also make the case that Portland making the playoffs and Henderson breaking out are independent of whether Holiday remains on the roster. They already have enough mentorship between Billups and Lillard. And Holiday's declining play as someone who averaged just 11.1 points and 3.9 assists last season in Boston isn't going to be the needle-mover to put a 36-win Blazers team over the top in a stacked Western Conference.
Outside of defensive impact, Lillard provides Portland with everything they wanted to get out of Holiday. He's also significantly cheaper and a better player (not to mention the previous ties to the Blazers franchise).
Portland should've flipped Holiday again regardless of their Lillard signing, but this just made it even clearer. Unfortunately, it seems unlikely they will do that anytime soon. They traded for Holiday with the intention of keeping him, and they can still use him as a stepping stone to get to the play-in while Lillard recovers.
But with Lillard returning and a full year to evaluate Henderson in an increased role, Portland will have to decide on its backcourt by next summer. And the odd man out should be the 35-year-old guard on the books for $104 million.