Recently, the Boston Celtics acquired Jrue Holiday from the Portland Trail Blazers. Holiday had previously been part of the trade that sent Damian Lillard to the Milwaukee Bucks two years ago, where he played a crucial role in clinching the championship for that team. Now, he’s back in Portland, which feels a bit like returning a borrowed library book. The Blazers appear ready to move forward, even as the Celtics have some work to do, particularly with Jason Tatum sidelined due to an Achilles injury next season.
On Monday night, the Celtics traded Holiday back to the Blazers in exchange for Anfernee Simons and two second-round picks, as reported by insider Shams Charania. At 35, Holiday still has three seasons left on his contract, while Simons, now 26, is entering the final year of his deal.
This move seems primarily strategic for both teams. The Celtics aimed to alleviate their payroll, while the Blazers are gearing up to secure a playoff spot for the upcoming season. We can really consider this trade from both angles.
Trail Blazers’ Perspective on the Holiday Trade
The Blazers were showing signs of life toward the end of last season. With players like Deni Avdija stepping up and Scoot Henderson making strides after a rocky rookie year, Portland managed to win 36 games, falling just shy of the play-in tournament.
It’s been four consecutive years since the Blazers missed the playoffs. While patience may be wearing thin after rebuilding around Lillard, rushing things has its pitfalls too. By bringing in Holiday, the Blazers signal a shift away from a full-on rebuild and appear ready to start competing for playoff positions again.
They certainly have a mix of young talent, but they lack a standout star. Henderson hasn’t yet lived up to expectations, and passing on Amen Thompson is starting to look like a miscalculation. Shaedon Sharpe has potential but hasn’t quite put it all together. The Blazers also hold the 11th pick in this year’s draft, which adds to their options.
After moving Lillard, the Blazers aimed for luck in the draft lottery, which didn’t pan out. This holiday trade looks like the front office scrambling to protect their jobs, especially with an eye on making significant moves ahead of the competitive 2026 NBA Draft.
Holiday, who was drafted in 2009, is in the midst of a contract worth $104.4 million over the next three years. Last season, he maintained a scoring average of 18.1 points and demonstrated solid shooting efficiency at 56.5%. He remains an excellent defender, but the Blazers will face challenges on offense.
Their defensive lineup, featuring Klingan, Camara, and Avdija, combined with Holiday, might create some mismatches against opponents. Both Henderson and Sharpe need to elevate their games for the offense to be even average, especially since they finished last year ranked 22nd in offensive efficiency.
Interestingly, the Blazers seem to be adopting a strategy similar to the Houston Rockets, following their signings of veterans to fast-track their rebuild. It worked for Houston, but there’s a concern that their younger core might be stronger than what Portland has. Perhaps they’ll consider flipping Holiday as his contract nears its end, but for now, they seem focused on the upcoming season amid a challenging Western Conference landscape.
Acquiring Holiday makes sense for Portland as they’re looking to compete, at least for the playoffs. Bringing in a solid player or veteran leader can be beneficial, and Holiday fits that bill. Still, it’s uncertain if he’ll turn out to be a burdensome contract down the line. Portland’s young roster still needs to mature significantly.
Blazers Grade: C
Celtics Grade from the Jrue Holiday Trade
The Celtics are bracing for a challenging season as Jason Tatum recovers from his Achilles injury. Even if he were healthy, Boston planned to trim payroll this summer. Tatum’s injury, however, gives them a timely opportunity to reset and strategize around his eventual return.
It’s clear the Celtics wanted to trade Holiday. It’s a bit surprising they found a market for him, considering his upcoming $37 million salary next season. However, this trade successfully achieves their goals for financial flexibility.
Will Simons have a future in Boston? It’s hard to say. He’s an impressive scorer who can create his own shot but is known for his weak defense, which doesn’t exactly align with the Celtics’ typical style. His expiring contract does give Boston options down the line, whether to boost the roster at the deadline or simply let it run out.
Getting away from Holiday without acquiring any unfavorable contracts is a win for the Celtics. When Tatum returns, Holiday wasn’t likely to have a significant role on the team. Looking ahead, the Celtics might also explore trading Kristaps Porzingis for assets, and discussions around moving Jalen Brown or Derrick White could be on the table too.
As Tatum recovers, the Celtics seem to be positioning themselves for a stronger future. Part of this strategy involves moving on from high-priced older players who may not contribute as effectively as before. In that light, this trade can be seen as another savvy call from one of the league’s top front offices.
Celtics Grade: A-
