Brown’s Potential Extension Makes or Breaks Celtics’ Future


Despite their initial heroics, the Boston Celtics failed to overcome a 3-0 deficit to the Miami Heat in the Eastern Conference Finals. Winning four games in a row with that deficit is almost impossible. After all, there’s a reason why teams are now 0-151 all-time when down 0-3.

The catch — postseason flameouts are nothing new for Boston.

Up 2-1 against the Warriors, Boston lost their composure last season in the NBA Finals. This season, the once heavily-favored Celtics fell to the eight-seed in Miami despite entering the Conference Finals as -550 favorites.

Boston remains an undeniable playoff-clinching team since Jayson Tatum joined the franchise to pair with the promising Jaylen Brown. Together, the Tatum-Brown combo was the perfect duo teams were looking for — switchable, multi-positioned defensive players with offensive creation. Think the healthy, younger and more successful version of the Kawhi LeonardPaul George Clippers.

But, the question now becomes this: has this team peaked?

It’s hard to deny the facts. The Celtics made the playoffs every year since Tatum joined in the 2017-2018 season. Four Conference Finals berths and a trip to the NBA Finals in a six-year window is hard to ignore, either. Now, combine that with their ages (each is under 26), production (each was above 26 points per game this season, including 30.1 for Tatum) and status within in the league (Tatum made All-NBA first team, while Brown made the second team).

Then again, consider the recent playoff disappointments. Or, Boston cooling off after such an astonishing start. Don’t forget the endless concerns with team chemistry, from the lack of a voice at head coach to potential damage in the relationship between Brown and the Celtics.

The last of these will prove to be the most critical for Boston to address. Yes, this team could maintain its current, promising ceiling around the Tatum-Brown core for the next decade if it wants to.



Brown agreed to a four-year, $115 million extension with the Celtics in October 2019. Now, Boston faces another round of extension talks with Brown, and with a heftier price tag.

Brown’s All-NBA selection means he could receive a five-year, $295 million supermax extension from Boston.

Except, there’s a few massive hurdles standing in the way.

The first is whether Brown wants to remain in Boston. Brown found himself at the center of the Kevin Durant trade sweepstakes and was clearly the main asset that had to be added to make the deal work.

A Durant trade to Boston never panned out. But, it also caused turmoil between Brown and the Celtics. For Brown, that was a clear stab in the back. As an unrestricted free agent in the summer of 2024, he could simply want a new situation.

Yet, there’s the financial side to consider. There are a lot of factors at play here.

First, Brown’s supermax extension can be signed as soon as free agency kicks off. Per Keith Smith of Spotrac, that looks something like this:

  • 2024-25: $50,050,000
  • 2025-26: $54,054,000
  • 2026-27: $58,058,000
  • 2027-28: $62,062,000
  • 2028-29: $66,066,000

Additionally, he isn’t be eligible for the supermax later on unless he makes All-NBA in the 2023-2024 season (Note: a player needs to make All-NBA in two of the last three seasons to be eligible for the 35% super max with 8% raises).

Tatum’s mega-raise also looms on the horizon, clocking in at five years and around $308 million (!!!).

Now, consider the NBA’s new Collective Bargaining Agreement and its many harsher penalties for teams in the luxury tax and second apron, among other new stipulations.

Boston faces the ever-daunting task of deciding on now or never with keeping the Tatum-Brown duo together.


For Boston, the Golden State and Miami series’ demonstrated Brown’s limitations in the playoffs. He’s turnover-prone and sometimes turns to hero ball with poor shot selection.

Especially against Miami this postseason, Brown struggled with turnovers (3.6 per game), passing (-0.2 assist-to-turnover margin), defense (1.1 steals per game, inconsistent effort) and efficiency (42% on over 19 shots per game, including 16% on over six threes per game).

Of course, that wasn’t Brown at his best. However, it’s a pattern that keeps manifesting itself in the playoffs for Boston. The Celtics need both Tatum and Brown to play like All-NBA players. In back-to-back high-stake playoff battles, Brown did not. That’s the current reality.

As The Lead noted early on in the 2021-2022 season, Boston’s success revolves, to an extent, around Brown’s improvements as a second star next to Tatum.

But at a certain point, Brown might just be who he is.

The question is: is Brown’s price tag worth that?

Most likely. Boston shouldn’t panic here. For starters, who exactly is replacing Brown? As we’ve seen in prior trades like that of Anthony Davis‘, it’s hard to make up the full value in trading someone of Brown’s caliber. At best, the Celtics may receive 75-80 cents on the dollar.

Also, don’t factor out the ages of Tatum and Brown, who are still young and have years of productivity left. Making four Conference Finals with neither forward above 27 is a testament to this team’s success with the Brown-Tatum tandem.

The biggest challenge for Boston is the financial side. Given the new CBA, Boston will be locking itself into this pairing for the next half-decade. If Brown demands out, that sets Boston back years behind the rest of the Eastern Conference.

In other words, the ball is in Brown’s court here. The question is whether he remains, and at what cost.

As the song from The Clash goes: “Should I stay or should I go?”

No matter the cost, Boston needs to play their hand wisely. It could make or break the future of this franchise.

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About Dominic Chiappone

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