The Boston Celtics have a big, interesting offseason ahead of them. After a surprising second-round playoff exit and a brutal Achilles tendon injury to Jayson Tatum, the Celtics could realistically shake up their entire roster ahead of the 2025-26 season.
With Tatum expected to miss most if not all of next season, the Celtics' payroll among the highest in the league, and the team having been sold to a new owner recently, there are legitimate questions about what Boston's strategy will be this summer.
Reports during the playoffs indicated that the team's new ownership will trade one or multiple key players from their 2024 title-winning roster in order to alleviate some of the cap worries, but ESPN insider Tim Bontemps made an even bolder suggestion: trade almost every one.
“You could make an argument — I think you could make a credible argument that the right thing for Boston to do would be to trade all four of its starters this year in the next two months, and get a ton of young players and draft picks,” Bontemps said on the ‘Hoop Collective' podcast.
While both Brian Windhorst and Tim McMahon immediately recoiled and expressed skepticism at the idea, Bontemps explained his rationale for why the Celtics could choose to overhaul their roster in this drastic of a manner, just one year removed from winning the NBA championship.
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“You’ve got Kristaps Porzingis, who is going into the last year of his deal, who's in his early 30s. You’ve got Jrue Holiday, who is in his mid-30s and is expensive. You’ve got Derrick White, who is 31, who will be 33 when Jayson Tatum is ready to be in the playoffs again and will never have higher value than he’s going to have now. And you could get an absolute metric ton for Jaylen Brown, and if you do those moves, you set yourselves up to potentially be ready [for 2026]. And I'm not saying you trade them all for, like, 19-year-old players. But you reorient the team so that in a year, when Jayson Tatum is ready to go in the fall of 2026, you have a younger core around him that you then try to contend for the next several years.”
It remains unlikely the Celtics will go as far as Bontemps laid out, but they will almost certainly trade at least one of their four starters. Porzingis and Holiday, in particular, are the most obvious choices considering Porzingis, who will turn 30 this offseason, is set to make $30.7 million in the final year of his contract. And Holiday turns 35 next month and is owed more than $100 million over the next three seasons.
Brown and White are also due massive amounts of money; Brown's five-year extension kicks in next season and is expected to be worth around $314 million, while White will be in year one of a four-year, $118 million extension.