The Boston Celtics are sending veteran guard Jrue Holiday to the Portland Trail Blazers in a salary-shedding deal that signals a financial reset ahead of a punishing tax season. In return, Boston receives Anfernee Simons and two second-round picks.
This trade, confirmed by ESPN’s Shams Charania on X, kicks off the NBA offseason with a clear message: Boston is getting serious about its books.
A Familiar Face Returns to Portland — Briefly or Not
This isn’t the first time Holiday’s name has landed in Portland’s roster sheet.
After being part of the 2023 blockbuster that sent Damian Lillard to Milwaukee, Holiday was briefly a Blazer before moving on to Boston. Now, he’s back — though whether he actually suits up in Rip City again remains to be seen.
At 34, Holiday brings veteran experience, strong defense, and playoff miles. But for Portland, who’s stacked with youth and building around Scoot Henderson and Shaedon Sharpe, the move feels more like a calculated asset play than a long-term fit.
One executive close to the situation put it bluntly: “They brought him in, but it wouldn’t surprise anyone if he’s on a different roster come October.”
Why Boston Pulled the Trigger
Boston’s cap sheet had become a landmine.
Before this move, the Celtics were projected to shell out nearly $500 million in roster and tax commitments next season. That placed them deep into the league’s dreaded second apron, where financial penalties become brutal — think lost flexibility, limited trade options, and an outright freeze on certain exceptions.
In simple terms: it was unsustainable.
Holiday, still reliable but on the downswing of his career, was a natural candidate to move. His averages in 2024–25 — 11.1 points, 4.3 rebounds, and 3.9 assists per game — were solid, but not untouchable.
His minutes were down. So was his impact.
He played just 20.6 minutes per game in 62 appearances. And while his playoff shooting bumped up a bit, his scoring didn’t: just 9.5 points per game in eight postseason matches. Boston needed to make a call, and they did — fast.
Anfernee Simons Brings Youth, Speed, and Scoring
Enter Anfernee Simons.
The 26-year-old had himself a season with the Trail Blazers, averaging 19.3 points and 4.8 assists per game. More than just a scorer, he’s developed into a reliable playmaker who’s comfortable with the ball in his hands.
He’s also on an expiring contract, giving Boston even more financial flexibility heading into next summer.
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2024–25 Simons Stats:
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Points per game: 19.3
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Assists per game: 4.8
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Field Goal %: 45.7
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3-Point %: 38.4
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Age: 26
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Contract: Expiring (2025)
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Simons could play a pivotal role next season, especially with Jayson Tatum recovering from an Achilles injury. Expect Boston to lean on him early, pairing him with Jaylen Brown to anchor the perimeter offense.
Who Else Wants Holiday?
Just because Holiday’s in Portland now doesn’t mean he’ll stay there for long.
Several teams are circling, watching closely. According to multiple league insiders, the Sacramento Kings, Dallas Mavericks, and Los Angeles Clippers have already shown interest in adding the two-time All-Star.
His playoff pedigree still matters. He’s smart. He defends. He shows up in big moments.
But Portland’s got a young core, and Holiday’s timeline doesn’t quite match up. So if they’re smart — and they usually are — this could be a move to flip him once again.
Here’s a look at how he stacked up last year compared to his career averages:
| Season | Points | Assists | Rebounds | Steals | FG% | 3P% | Minutes |
|---|---|---|---|---|---|---|---|
| 2024–25 | 11.1 | 3.9 | 4.3 | 1.1 | 44.3% | 35.3% | 20.6 |
| Career | 16.4 | 6.4 | 4.1 | 1.5 | 46.0% | 36.2% | 32.4 |
That’s a notable drop-off. But for a contender looking to solidify its backcourt defense and gain a locker room leader? Still valuable.
Celtics Face Tough Offseason Decisions
This won’t be the last move the Celtics make. It can’t be.
They’re still over the first tax apron, even after shedding Holiday’s salary. Simons’ expiring deal helps, but Boston needs to think carefully about how it approaches the rest of its summer.
Expect decisions on Payton Pritchard and Al Horford soon. There’s even been light chatter around Derrick White, though nothing appears imminent there.
One league source described Boston’s approach as “surgical and swift.”
Maybe even a little cold-blooded.
They just won 64 games and fell short in the playoffs. Now they’re reshuffling, retooling, and trying not to let this window slam shut.
Portland’s Next Move Could Be a Trade — Or a Buyout
Portland doesn’t have to keep Holiday. They may not even want to.
He’s good enough to fetch another first-round pick if packaged right. And if no deal materializes, a buyout later in the season isn’t off the table. But Blazers GM Joe Cronin has options, and that’s the key here.
The Trail Blazers are young, talented, and nowhere near contending. Bringing in Holiday could be about leadership, or it could just be good business.
For now, they’ve bought flexibility. Again.
