Has Jaylen Brown played his final game for the Boston Celtics?

After being eliminated by the eighth-seed Miami Heat in Game 7 of the Eastern Conference Finals, the Boston Celtics will have a tough decision to make this summer. They again failed to win a championship with their current core, which potentially leads to the big decision regarding whether to trade All-Star Jaylen Brown. Brown can sign a designated veteran player extension (a.k.a. a supermax extension) this summer worth $295 million, which would pay him nearly $60 million a year beginning after next season.

Although Brown has been the Celtics’ best player behind Jayson Tatum, any team would think twice about offering a player that much. Especially with an unforgiving new collective bargaining agreement (CBA), which will make it almost impossible for a team to go deep into the luxury tax thanks to the tough new penalties for doing so.

If the Celtics extend Brown, his contract, in combination with Tatum’s, would mean that their two best players would combine to make around $90 million for the 2024–25 season and give the team a projected payroll of at least $175 million split amongst just eight players. For reference, the salary cap is expected to be around $143 million that year, and the luxury tax will be $173 million.

Keeping Brown could ensure that the Celtics have a chance to make the NBA Finals every season for the next several seasons. Then again, keeping Brown could result in Boston staying over the second luxury tax apron, which is $17.5 above the tax line, and being handcuffed. Beginning next season, they wouldn’t be able to use their mid-level or taxer-midlevel exception, sign most buyout candidates, trade first-round picks, or combine players’ salaries to make trades.

They couldn’t even use cash considerations in deals or make ones in which they took back even a dollar more. Essentially, just about every tool that contending teams use to try and build around their core would be severely restricted. While they would still be able to re-sign their own players, being barred from signing buyout players and making most trades means that they would have to rely heavily on Tatum and Brown for the next several seasons.

That is a lot of pressure, and the Celtics would essentially be stuck with mostly the same roster for the foreseeable future, especially when Tatum becomes eligible for an even bigger extension of his own in a couple of seasons.

Ultimately, the decision may come down to the Celtics. If they offer him the full super-max extension, then he would probably have a hard time turning down nearly $300 million. However, if they offer him less in an attempt to save money, he may reject the offer and take his chances in free agency in the summer of 2024.

With the deadline to agree to a supermax set for Halloween 2023, we’ll know where things stand before the start of next season. If an agreement isn’t reached, Boston could potentially trade Brown well before next summer, perhaps even during next month’s NBA Draft, where many blockbuster deals take place. Especially with several teams open to trading their lottery picks.

Of the two options, trading Brown this summer might be the best option given the new CBA, though there’s no guarantee that they would be better without him.