The Boston Celtics have been among the league’s top teams over the last three seasons. This season, they lead the Eastern Conference with a comfortable six-game cushion over second place. The guys in green are rolling – and should be considered title favorites as long as their top-6 arearound.
So why are we talking about trades?
According to The Ringer’s Howard Beck, a serious salary cap reckoning could be coming for a number of top teams. The new CBA fully kicks in next season, and teams over the second salary apron will be severely penalized. Not only are there new barriers to team-building – like the loss of free agent exceptions and a ban on aggregating salary in trades – but teams will have future first-round picks frozen (and, eventually, moved to the end of the round) if they remain over the apron three out of five years.
The Celtics are over that apron this year and project to be for the foreseeable future. Luckily, this year is a “bonus” season before those penalties come into play.
Going forward, however, President of Basketball Operations Brad Stevens will have to balance championship aspirations with future penalties.
“It’s going to be challenging to keep Jayson Tatum, Jaylen Brown, Kristaps Porzingis, Jrue Holiday, and Derrick White in perpetuity, even if they were to win the title,” Beck wrote. “Does that mean shedding a talented role player like Holiday?”
The answer to Beck’s question is probably ‘no.’ Holiday is making around $35 million this year, with a player option worth $37 million next season. The most likely outcome for that pending option is he denies it in favor of an extension in the ballpark of $30 million a year for two or three seasons. I think Boston would happily pay that for their defensive focal point. Plus, that would be a moveable contract if management saw an upgrade in the future.
There are a few scenarios that could change that calculation. If Holiday wants much more than that, then he probably has to go – either by declining his player option to become a free agent or opting in without an extension plan, which would probably lead Boston to find a trade partner. All we’ve heard from Holiday thus far, though, is that he’s all-in on getting an extension done. Fingers crossed.
Boston could go in a different direction with Holiday if they flame out in the playoffs. It would have to be a pretty bad collapse – with everyone healthy – that made clear this wasn’t a championship team. That’s not likely.
Beck’s source is an NBA executive who thinks Boston has to “figure out who’s expendable and who’s not.”
To that I say, “not yet.”
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There’s nothing keeping the Celtics from running it back next year. Boston’s cap sheet does explode once Jaylen Brown’s extension kicks in, but that only makes it harder to add higher-salary free agents and make midseason trades. Teams don’t need to do a lot of that when their rosters are contenders.
The only players that could leave Boston as free agents this summer are Luke Kornet, Svi Mykhailiuk, Xavier Tillman, Oshae Brissett (player option) and Holiday (player option). Out of those guys, only Holiday is a truly core piece of the rotation.
So no, it’s not yet time to think about whether Holiday is “expendable.” This team is great and should stay untouched at least through next season.
But Beck also suggested – with the help of a Western Conference executive – that Boston will be looking to move off of Jaylen Brown sometime soon.
“No one is predicting Brown will be moved this summer – particularly with Boston in first place,” Beck said. “But the Celtics will eventually have to confront the financial realities of the new CBA.”
This one is tricky, because Jaylen Brown is one of the main reasons Boston is contending for a championship. Take him off this Celtics team and there is not enough shot creation, not enough wing defense, not enough talent for the team to win it all.
Fast-forward to the 2025 offseason, though. Maybe the Celtics have secured Banner 18 (or 19?), achieving what they’ve struggled to do for so long. Al Horford is saying goodbye to an incredible career at the age of 39, leaving a hole in Boston’s frontcourt that will not be easily filled. Holiday is 35 years old, with a year left on his deal, and Boston has to decide how much money to give Derrick White, who likely is worth more money after two years of flirting with All-Star status.
Now, consider that Tatum will start his supermax extension that season. His salary and those of Brown and Porzingis will total $140 million, close to the salary cap.
Filling out the rest of the roster at that point will be exceptionally difficult. I’m not saying the Celtics will have to move Brown to field a team, but they won’t be able to keep everyone around. You can start to see what Beck’s sources are getting at.
If they do choose to move Brown, “Jaylen would set the record for the biggest return,” an executive told The Ringer. “It should be a Durant-type deal.”
Kevin Durant was traded just over a year ago for Mikal Bridges, Cam Johnson, Jae Crowder, and four first-round picks. That kind of return would keep Boston competitive while saving money and loading up on picks.
Again, it’s too early to be thinking about a trade of this magnitude. But you know Brad Stevens is thinking about the team’s cap future; we should, too.
