The Boston Celtics acquired Jrue Holiday from the Portland Trail Blazers after he was dumped by the Milwaukee Bucks in the Damian Lillard trade two years ago, and he proved to be the team’s final piece to a championship puzzle. Now Holiday is returning to Portland like a lent library book, signaling the Blazers are ready to take a step forward while the Celtics retool with Jayson Tatum sidelined for all of next season with a torn Achilles.
The Celtics traded Holiday back to the Blazers on Monday night for Anfernee Simons and two second round picks, according to insider Shams Charania. Holiday just turned 35 years old and has three seasons remaining on his contract. Simons is entering the final year of his contract and recently turned 26 years old.
The Celtics did this trade to shed salary. The Blazers did this trade to try to make the playoffs next season. Let’s grade the deal from both sides.
Trail Blazers grade for Jrue Holiday trade
The Blazers finally started to be frisky at the end of last season. Deni Avdija emerged as the team’s best player, Toumani Camara made Second-Team All-Defense, and Scoot Henderson took a little step forward after a tough rookie year. Portland won 36 games, and finished three games outside of the play-in tournament.
The Blazers have missed the playoffs for four straight years. Patience might be running out on the team’s post-Damian Lillard rebuild, but there’s real downside to accelerating too early. By trading for Holiday, it feels like the Blazers are signaling the end of their tanking era, and are ready to start competing for a playoff spot.
Portland has plenty of good young players on the roster right now, but they don’t have the guy. Henderson has been disappointing in his first two seasons, and passing on Amen Thompson for him looks like a mistake. Shaedon Sharpe is talented but has never put it all together. I thought Donovan Clingan was fantastic defensively as a rookie, but his offense remains a work in progress. Portland also has the No. 11 pick this year.
The Blazers were praying for lottery luck after they traded Lillard, and it never came. Trading for Holiday feels like the sign of a desperate front office that is trying to save its job rather realizing they still aren’t in position to push forward, especially not ahead of a loaded top-three in the 2026 NBA Draft.
Holiday was drafted way back in 2009. He’s on a deal that pays him $104.4 million over the next three years, which includes a $37 million player option for the final season when he’ll be 37 years old. He finally started to look his age last year as his scoring (18.1 points per 100 possessions) and scoring efficiency (56.5 percent true shooting) both tailed off. He’s still a very good defender, but the Blazers’ offense has to be a big question after this trade.
The Blazers are trying to win with defense. A lineup of Clingan at center, Camara and Avdija at forward, and Holiday in the backcourt is going to be a nightmare to score against. Henderson and Sharpe will need to improve to help the offense get to even an average level (Portland finished No. 22 in offensive rating last year).
It feels like the Blazers are following the Rockets’ model after they signed Fred VanVleet and Dillon Brooks to accelerate their rebuild. That worked out wonderfully for Houston, but I fear the Rockets’ young core is better than Portland’s. Maybe the Blazers will flip Holiday eventually as his contract gets closer to expiring. For now, I worry they’re taking themselves out of the Cameron Boozer/AJ Dybantsa/Darryn Peterson race to chase a low seed in a loaded Western Conference.
Holiday made more sense as a trade target for contenders. The only thing the Blazers are contending for is the No. 8 seed. There’s certainly no harm in acquiring good players and good veteran leaders, and Holiday checks both boxes. I just worry he’s verging on being a bad contract after a down season this past year, and that Portland’s young core is still missing the guy to build around.
Blazers grade: C
Celtics grade for Jrue Holiday trade
The Celtics can’t compete next year with Jayson Tatum recovering from a torn Achilles. Boston was going to shed payroll this summer even if Tatum was healthy, and his injury offers them the chance to do a hard reset to build their next great team around Tatum when he returns.
Ditching Holiday was an obvious move. It’s a little surprising he still had a market given that he’s on an ascending contract that goes from 32.4 million next season to $37 million in the final year of his deal at age-37. The Celtics wanted cap relief and picks back for Holiday, and they accomplished both in this deal.
Will Simons be part of Boston’s long-term plans? I doubt it. The slippery scorer is a talented pull-up shooter who can generate offense off the bounce, but he’s one of the worst defensive guards in the league, and just doesn’t feel like a Celtics type of player. That’s perfectly fine because Simons is on an expiring contract that Boston can flip at the deadline if he plays well, or just let expire.
Getting out of Holiday’s deal without having to take on any bad money is a win for Boston. Holiday was never going to be on this team when Tatum gets healthy. The Celtics’ next move is likely trading Kristaps Porzginis for assets. It would be more surprising if Boston traded Jaylen Brown or Derrick White this summer, but everything should be on the table.
The Celtics are building for the future as Tatum recovers. Part of that is getting off highly-paid older players who aren’t as good as they once were. In that regard, this is another sharp move from one of the best front offices in the game.
Celtics grade: A-
