Why the Jaylen Brown Extension is a Win for the Celtics

Jaylen Brown received $304-million guaranteed. He signed the largest contract in NBA history, garnering a trade kicker that could increase the size of the super max contract. The stick shock sent some fans into a frenzy. In this era of the league, it doesn’t exactly lock him into Boston through 2029, as it says on the paper, either.

Yet the Celtics walked away from negotiations on Tuesday as a significant winner, with plans to reintroduce Brown as one of their designated superstars at a press conference in Cambridge on Wednesday at his ongoing Bridge education program for local high school students. Brown did not receive a player option, a first for a player signing the designated veteran extension introduced in the 2017 collective bargaining agreement to keep top-end stars with the team that drafted them. Boston did so with Brown and received an added year of team control.

The Celtics successfully utilized their leverage as the only team that could approach $300-million, paying him the full 35% of the cap beginning in 2024-25 after one more season where the team is relatively cost-controlled. Then, the mega deal hits beginning just over $52-million and concluding with a fully guaranteed $70-million season in 2028-29. As risky as the contract looks on paper, it’s the price of doing business with NBA superstars now, and while weaknesses in Brown’s game may raise legitimate questions about his worthiness, that argument in a vacuum ignores the context of the situation both sides found themselves in.

Debate over the player option, and the trade kicker Brown received, reportedly worth well below the 15% max the CBA allows, strung out for weeks as both sides tried to garner protection in any potential trade that could emerge down the line. That includes Brown asking out, signaling discomfort and uncertainty over his future in Boston this past season in multiple interviews and internally, or Celtics navigating an increasingly hefty cap sheet by moving Brown once his contract balloons by 8% several times annually. Brown is trade-ineligible until July 26 next summer. In that short term, Boston’s leverage becomes the rule book and five years of team control, similar to Portland. The Trail Blazers are sitting patiently on Damian Lillard’s trade request with years of team control.

Brown could not receive a no-trade clause in negotiations, but the trade kicker isn’t nothing. Once the deal extends into its later stages, when the Celtics would become more likely to trade him than in the near term, Brown may carve out some room beneath his 35% max salary to receive extra money from the trade kicker. You cannot exceed the max, like Bradley Beal would’ve with his trade kicker going to Phoenix this summer, so that bonus essentially becomes moot early in a max contract like Brown’s. Later, though Brown’s contract increases each year, it could do so at a rate below the NBA’s cap. Whatever room Brown has beneath his new max salary in that year becomes his trade bonus, spread out over the remaining years of the contract. Depending on what percentage, it’d probably tack on a few million annually to the back end of the deal if Boston, if anything.

That does matter in a trade negotiation though. While Brown’s outgoing sum salary would become his next team’s problem, the two sides need to make the money work to complete the deal, and the new CBA changes the math for a team like the Celtics bound to cross the second apron when the extension begins. Second apron teams need to match trade money dollar-for-dollar, and cannot aggregate salaries to do so. Whichever player(s) the Celtics target may make a little more, or a little less, money than Brown, and his decision on his trade kicker could allow for and prevent certain trades at that point. Kyrie Irving’s trade to Boston in 2017, for example, happened in part because Irving waived his trade kicker to come to the Celtics. It happens.

Brown’s excellent agent Jason Glushon bet on it mattering in this case too, and the Celtics successfully added a rare extra year of team control onto an extension. The super max money made sense for both sides. Brown couldn’t receive anything comparable elsewhere, especially not by leaving in free agency. The Celtics, as mentioned, benefited from both the trade implications of a higher salary and from simply keeping him under team control long-term. They did this deal with a vision of Jayson Tatum and Brown playing together long-term. Of course, the money becomes challenging once Tatum makes over $50-million himself beginning in 2026.

Don’t forget the conversation before the uneven postseason run and sour taste Game 7 against Miami left in many evaluations of Brown. His All-NBA push drew support, even campaigning, to ensure his entry as a forward where he’d acquire the ability to sign a super max deal. It mattered then because the inevitable 140% raise in the CBA for Brown probably wouldn’t compel him to sign this summer, as the 120% raise couldn’t last year. If Brown never made All-NBA, he and the Celtics likely wait out a tenuous contract season with the stakes already high for everyone involved before taking him to a free agency he would’ve headlined. The super max, despite its staggering price tag, made this easy. It also gained Boston that valuable sixth year on the deal, which would make it difficult even in three years for Brown to ask out without the Celtics leveraging a significant return.

That’s betting on Brown fulfilling his promise as a top-15 player. Injuries to Zion Williamson, Brandon Ingram, LeBron James, Kevin Durant and others undoubtedly played a significant role in Brown’s ascension to All-NBA status. He also made the Second Team by a significant margin over the third team forwards. The defense must improve. The offense must grow more connected, particularly with Tatum. The leadership, between Brown and the team’s other stars, must fill what Boston gave up in Marcus Smart. But even as someone who turned an eye toward Kevin Durant last summer, and listened to ideas on alternatives to paying Brown, none emerged and the Celtics remain convinced Brown and grow alongside Tatum into a champion.

If they do, this deal becomes a no-brainer.