Celtics
"They probably are going to have to make multiple more moves."
Celtics
Celtics Al Horford, Derrick White, Jaylen Brown, Jrue Holiday, and Kristaps Porzingis on the bench in January. Barry Chin/Globe Staff
By Hayden Bird
June 24, 2025 | 3:29 PM
4 minutes to read
The Celtics began what could be an offseason of difficult cuts on Monday with the report that the team was trading Jrue Holiday to the Trail Blazers in exchange for Anfernee Simons and two second-round picks.
The salary-shedding measure is part of a larger process the team appears committed to in order to escape the harsh penalties of the NBA’s second luxury tax apron.
Given the specific luxury tax motivation, and Jayson Tatum’s recovery timeline following an Achilles rupture during the playoffs, it points to a potential clearing of the decks moment for Boston’s roster in the 2025-2026 season.
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Here’s what experts had to say:
Shams Charania
The NBA insider broke the news of the Holiday deal on Monday evening. He emphasized that, at a general level, Boston is still working on additional deals.
“The Celtics remain engaged in trade talks surrounding multiple key players on the roster, sources said,” said Charania.
He also gave a snapshot scouting report of Boston’s newly acquired guard.
“In Simons, the Celtics get a 26-year-old scoring guard who is comfortable shooting from distance,” Charania explained. “Simons has averaged nearly nine 3-point attempts per game over his past three seasons, a valuable skill in Celtics coach Joe Mazzulla’s 3-pointer-heavy offense.”
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John Hollinger
Looking at the Celtics’ side of the trade, The Athletic writer praised Celtics president of basketball operations Brad Stevens for pulling off a salary dump while receiving draft picks for it.
“The most amazing thing about this trade is that the Celtics got off the final two years of Holiday’s deal while receiving draft picks instead of sending them out,” Hollinger noted. “The three years and $104.4 million left on Holiday’s deal projected to be deeply underwater value-wise; I wondered whether the Celtics would have to give up two firsts to move off his money or whether they could get away with one.”
Looking at the other side of the trade, he was left scratching his head.
“As for Portland, I’m baffled,” Hollinger said.
“Let’s wait and see what else the Blazers cook up this offseason; maybe they can wave a magic wand and turn [Deandre] Ayton into a point guard and a shooter,” he concluded. “At this moment, however, I am flabbergasted that they sent out draft capital to turn Simons into Holiday. Even if you think Holiday is the better short-term fit, the nine-year age difference on a team that is not exactly contention-ready is a major minus for the out years, and they got nothing else back for their trouble. I don’t get it.”
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Bobby Marks
The former Nets general manager (now a front office insider) unsurprisingly took the long view of the Celtics’ road ahead as Tatum recovers. He took probably the harshest view of Boston’s upcoming year.
“This certainly is the bridge year,” he said of the upcoming Celtics season. “I don’t want to say go into a fire sale, but you’re basically going to probably be positioning yourself potentially a lottery pick here as far as where this roster is going.
“You wait until Tatum gets back and you figure out what you want to do with your roster, but you do have to have I would say a winning team when he does return here.”
Marks shared a detailed graphic of the Celtics’ roster, and the remaining $18 million in cuts that Boston could be looking to make.
Ben Rohrbach
The Yahoo senior writer jumped into the financial details of Boston’s offseason path.
“Between salary and luxury taxes, the Celtics were on pace to spend almost $500 million in payroll for next season. That is untenable,” Rohrbach pointed out, “especially for a team that no longer feels like a legitimate title contender. Boston’s new owner, Bill Chisholm, does not want to lose money on the team he just bought for $6 billion.”
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“Every dollar cut is exponential savings,” he added. “Boston remains about $18 million above the second apron after Monday’s trade.”
Brian Windhorst
As one of ESPN’s regular insiders — especially when it comes to periodically sensing additional moves — Windhorst was tasked with trying to foresee what might come next for the Celtics during a Tuesday appearance on “Get Up!”
“[Kristaps] Porzingis I definitely think they’re in discussions with,” Windhorst said of the Celtics’ center possibly being the next player to be traded.
“They would need someone to sort of be a big man, a starting level big man for Porzingis if they made this deal,” Windhorst concluded. He turned his attention to the Jaylen Brown-Derrick White duo.
“As for the other two star players, I don’t think Jaylen Brown and Derrick White are players that they want to trade. Having said that, if somebody calls with a gigantic offer, I think that they would have to discuss it. I think they’d be looking at their other supporting players, maybe like a Sam Hauser that they would be looking to do.”
Windworst’s underlining takeaway is that the Celtics are not done.
“They probably are going to have to make multiple more moves to save this money that they need to save.”
Hayden Bird
Sports Staff
Hayden Bird is a sports staff writer for Boston.com, where he has worked since 2016. He covers all things sports in New England.
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