Two days after the Boston Celtics’ Game 5 death rattle, their season came to an end in a merciless, 38-point blowout loss to the New York Knicks. As Celtics players watched the margin on the scoreboard widen, it was natural to consider how unexpected a scene it was. The Celtics entered the season as overwhelming favorites to repeat as champions, only to succumb in tragic and stunning fashion in the second round of the playoffs.
Plenty of keys have already been clacked on just what a bummer Jayson Tatum’s Achilles injury is for the Celtics and the NBA as a whole. But Tatum’s injury is more than a tragic tale. It’s an inflection point in Celtics history. He underwent surgery for a ruptured right Achilles last week, and there’s no timetable for his return, but players who have gone through similar procedures tend to miss a year. How ownership and the front office handle the next 12 months will determine whether these Celtics are able to carve out a dynasty after a traumatic setback or whether the window on a multiyear run just slammed shut.
Injury or not, the Celtics have long been aware of the financial burden staring them down this summer. A historic tax bill awaits unless they trim payroll, and Tatum’s injury likely knocks them out of the title chase for a season.
And so that’s the tightrope the Celtics will try to walk. How do they trim payroll while, at the same time, priming themselves to bounce back into contention upon Tatum’s return? And how soon will they be competing for the Larry O’Brien Trophy yet again?
It’s perhaps the toughest test yet for Celtics president of basketball operations Brad Stevens. He’s built one championship roster. Now he has to build another. The task is singular, but he has many doors to choose from. Here they are, each one riskier than the last.
Door No. 1: Status Quo
In other words, stick to the plan and get under the second apron.
The Celtics were already bracing for a salary-cap pinch in 2025 and the reality of needing to trade at least one of their four most expensive players around Tatum: Jaylen Brown, Kristaps Porzingis, Jrue Holiday, or Derrick White.
Boston is projected to be about $24 million over the second apron and $40 million over the luxury tax line while paying just 11 players next season. Trading any one of the four players above while taking minimal guaranteed salary in return would get them under the second apron, but they would remain a luxury tax team.
They could play out the season, see what Brown can do as a no. 1 option and whether Payton Pritchard can make a leap. Maybe they hope Tatum can return next postseason, but that’s a long shot and carries the risk of rushing Tatum back from a severe injury.
The Celtics could still go this route if ownership signs off. (Ownership of the franchise is transitioning to Bill Chisholm, but Wyc Grousbeck is expected to remain in charge until 2028.) But paying even a trimmed luxury tax bill seems irresponsible for a team that failed to make it out of the second round, will be without its best player for 2025-26, and needs to be mindful of the repeater tax.
Boston will have to pay the steep financial penalties of the repeater tax if it’s above the line next season. Meanwhile, going under the tax line for two straight years would allow the Celtics to avoid the repeater tax until 2030 and provide the front office the flexibility it needs to reopen the championship window when Tatum returns.
Door No. 2: The Gap Year
The Tatum injury could make Boston’s summer dilemma easier and give ownership the cover it needs to dramatically reduce payroll and avoid the tax altogether while keeping its core of Tatum and Brown.
To do that, the Celtics would need to cut $40 million in salary, plus whatever it would cost to fill out the roster and remain under the tax. Going through this door means keeping Brown and trading two of the Porzingis-Holiday-White trio instead of one. (Sam Hauser, the sharpshooter who signed a four-year, $45 million contract last summer, could also be a casualty of downsizing.)
If the Celtics accept they aren’t competing for a title in 2026, then they can spend the season mining the G League and free-agency bargain bin for players who can help, while developing prospects Baylor Scheierman, Jordan Walsh, and Neemias Queta into rotation players.
But this path is more difficult than it sounds. Porzingis, at his age and with a spotty health history, won’t be easy to move. Everyone loves Jrue Holiday, but because he’s approaching his 35th birthday, teams won’t exactly be lining up to pay him more than $100 million over the next three seasons. The Celtics will have to attach sweeteners to persuade teams to take those veterans off their hands, and there aren’t many teams with the cap space to make it happen. Stevens has three tradeable future first-round picks (including the no. 28 pick this June), and it could take all of them.
Door No. 3: The Compromise
The other option is to trade White. Twenty-nine teams would love to have White on their roster, and the Celtics could probably get something valuable back.
He’s as close to a core piece outside of Tatum and Brown as it gets, particularly with Tatum out. The Celtics would still need to discard another salary, and trading White could close Boston’s window for more than one season.
But Stevens outsmarted the league by trading for White three years ago. Could he do it again by finding the next White?
White is 30, two years older than Brown and four years older than Tatum. His age doesn’t infringe on their timeline now, but eventually it will. Although White has outperformed the annual value of his contract, he’s still an expensive no. 3 option when considering the investment Boston has made in its top two players.
If the Celtics can’t find landing spots for both Porzingis and Holiday, they may be forced to explore what is sure to be a frothy market for White.
Door No. 4: A Jaylen Brown Trade
We all knew this door was coming. It’s scary and mysterious, like the dark elevator in Severance. The Celtics could exhaust their assets to move two expensive veterans, or they could do something more drastic and take calls on Jaylen Brown.
Brown is a Boston legend who helped deliver duck boats for the first time in nearly two decades. But because of a collective bargaining agreement designed to curb rosters as expensive as Boston’s, the Celtics will have to decide at some point whether they can afford to pay Tatum and Brown more than $600 million over the next four seasons.
The reigning Finals MVP wasn’t as good this postseason, but he’s still Boston’s most valuable non-Tatum player (he’s ranked no. 21 on The Ringer’s most recent Top 100 list). Trading him would save the Celtics more than $236 million over the next four seasons, including $53 million next season, in addition to bringing assets back.
But that’s not an easy salary to move, and the Celtics would have to find a way to take little to no guaranteed money back to make it worthwhile.
The easy place to go is Brooklyn, the only team operating with max cap space in a summer with an underwhelming free agent class. The Celtics could offer to trade Brown into their cap space for an assortment of picks. But they’d also be negotiating in a vacuum, which isn’t great for leverage. To get enough from Brooklyn to warrant trading a franchise player, the Celtics might need to find at least one other taker.
If no other team has cap space, then the Celtics would need to search the league for non-guaranteed contracts that they could waive and create the financial relief they need. Unfortunately for them, most contracts across the league are fully guaranteed, and there aren’t many that qualify.
Which brings us to an admittedly wild option: Trade Brown to New Orleans for Zion Williamson, a 2026 pick swap with Milwaukee, and a Pelicans 2029 first, then waive Williamson before his July 15 guarantee date.
If this seems nuts to you, it should! Trading away a franchise player for a player as polarizing as Williamson, and then waiving him, is downright bananas. But part of me can’t help but think it might just be crazy enough to work.
That deal would save the Celtics the whole of Brown’s contract, drop them under the luxury tax, and give them valuable assets to retool the roster.
The 2025-26 season wouldn’t be pretty. There’d be a lot of watching White and Pritchard cook while waiting for Porzingis’s deal to expire. Losses would pile up, but the Celtics control their own 2026 pick and would potentially have the right to swap picks with a Bucks team that could be completing a season without Giannis Antetokounmpo. Either pick could end up in the top 10 of a well-regarded 2026 draft and be a valuable trade asset.
Fast-forward a year, and the Celtics could go into the 2026-27 season with Tatum, White, Holiday, Pritchard, and the assets needed to reopen a multiyear championship window.
Stevens masterfully constructed a roster that won a title, and now he’s faced with dismantling it while keeping Boston’s long-term championship hopes alive. There are no perfect options, but that’s what happens when your star player suffers one of the most devastating injuries in the sport.
Pick a door, and go through.