Despite Extension, This Season Could Be Jaylen Brown and Jayson Tatum's Last Chance at a Championship Together

Three factors suggest despite Jaylen Brown's veteran supermax extension with the Celtics, his time with the franchise is running out.

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The Celtics already made the difficult decision to part with the longest-tenured player on the team, Marcus Smart, after nine years in Boston, and Grant Williams, a valuable member of their rotation and Jayson Tatum's closest friend on the roster.

And while they agreed to a veteran supermax extension with Jaylen Brown on Tuesday, making him ineligible to get traded this season, it could still be the All-NBA wing's last one in Boston.

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The two-time All-Star's five-year, $304 million deal is the most lucrative contract in the NBA's history. While some are at least pretending to get worked up over that, the Georgia native was merely next in line for a title passed around quickly. It won't be long before someone else signs for more.

Tatum, for instance, is eligible for a veteran supermax extension next summer. If the league's salary cap increases by ten percent over the following two seasons, the two-time All-NBA First Team selection's five-year contract projects to be worth $338 million.

If the Celtics' star tandem's still on their books in 2025-26, they'll account for roughly 70 percent of their cap space. As if building around them under that circumstance with a new collective bargaining agreement that's more punitive isn't challenging enough, Brown's extension gets more expensive each season of its existence.

It could've come with an eight percent annual decrease. Instead, it will make staying under the second apron even more difficult. Crossing that threshold doesn't just come with a heavy financial tax. Restrictions for teams that go over include not receiving more inbound salary than what they're sending out in a trade.

They also can't stack veteran minimum contracts to acquire someone. Other repercussions include not having access to the mid-level exception, and their first-round pick can fall to the end of the round. And the punishments are worse for repeat offenders.

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So, while Brown's deal doesn't include a player option, there's considerable value in the trade kicker it has, allowing him to receive a percentage of the remaining money owed to him at the time of the transaction. While it could've maxed out at 15 percent, Adam Himmelsbach of the Boston Globe reports the kicker will be worth less than that.

Still, whether he wants a change of scenery, perhaps for the chance to become the unquestioned face of a franchise, or the Celtics decide that building around Tatum and Brown on supermax extensions under the new collective bargaining agreement is untenable, there's a significant chance he receives that bonus money.

Boston could also decide it's willing to do so for a different co-star. Joel Embiid recently questioned whether his championship pursuit will force him to leave Philadelphia. Donovan Mitchell, extension-eligible next summer, may be entering his last season with the Cavaliers.

The Mavericks are coming off a campaign where they failed to reach the playoffs and spent the end of the regular season tanking to avoid the play-in tournament. Doing so allowed them to keep a first-round pick that was top-10 protected and otherwise would've conveyed to the Knicks as part of the trade for Kristaps Porzingis, who's now trying to help the Celtics raise Banner 18 to the TD Garden rafters.

If Dallas underwhelms in 2023-24, perhaps Luka Doncic will ask out after the season's conclusion. Teams are also monitoring how much longer Giannis Antetokounmpo will remain with the Bucks. Milwaukee retained Khris Middleton and Brook Lopez this summer, but the former MVP's surrounded by an aging core.

So, even though Brown and Tatum have led Boston to the Eastern Conference Finals four times in their first six years together, came within two wins of a title, and are now entering their primes, the nature of the new CBA, structure of the former's contract, and the stars who could soon be available suggest Brown's time with the Celtics is running out.

Further Reading

Celtics, Jaylen Brown Agree to Richest Deal in NBA History

Why Celtics Should Enter 2023-24 Season Optimistic About Most Important Area of Improvement

Payton Pritchard Officially Named to USA Select Team

Amid Negotiations with Celtics, Jaylen Brown Continues Giving Back to Community He Stars In: 'Nothing Fills My Heart More'

Intriguing Option for Celtics May Soon Become Available

Joel Embiid Processing Sixers' Future, Could He Join Jayson Tatum on Celtics?

Celtics Reportedly Show Interest in Signing Austin Rivers

Gabe Vincent Says He Sensed Celtics Were 'Not Fully Right Internally' in Eastern Conference Finals

Sam Cassell Discusses What Brought Him Back to Boston and What He'll Bring to the Celtics

Oshae Brissett on Joining Celtics: 'I Just Want to Go Win'

Marcus Smart Reflects on His Time with Celtics: 'I Left Everything I Had'

Evaluating Celtics' Options in Free Agency