Will Jaylen Brown use strategic play in supermax negotiations with Celtics?

Jaylen Brown recently left the country for an international commitment with the NBPA so there has been no movement on his supermax extension talks with the Celtics this past week amid a busy offseason for Boston.

“I can’t really talk about it but it’s been all good discussion,” Stevens said last week in Las Vegas of negotiations with Brown. “We want Jaylen to be here for a long, long time, and we’ve made that clear. We’re looking forward to all sitting down and we have time here. I probably shouldn’t say anything else, but I feel optimistic.”

Despite Stevens’ optimism, the absence of a supermax deal nearly three weeks into free agency is a little bit noteworthy given the factors in play for both sides. There are issues to work out per sources (trade kicker possibilities, player option for a fifth year, etc.) that come as no surprise at this point. However, it will be interesting to see just what side gives in on their preferred terms for a deal.

The Celtics would seemingly have the trump card on a lot of fronts since they are the only team that can give Brown a supermax deal (35 percent of the cap with 8 percent yearly raises) for now once his current deal expires in 2024. That should give the organization plenty of incentive to try to hold the line when it comes to making the deal as long as possible (no player option in year five) and avoiding a trade kicker (which could complicate a future deal for them involving Brown with the new CBA restrictions).

Brown and his camp however likely see the long-term possibilities in play here if they sign the deal. After Boston traded for Kristaps Porzingis back in June and immediately rewarded him with a two-year extension, Boston’s long-term financials suddenly got very pricy when accounting for Jayson Tatum’s upcoming supermax extension.

Without winning a title in the next couple years, Brown could be the odd man out if the team decides they need to rebalance the roster for financial reasons with big deals for Tatum, Brown and Porzingis on the books taking up nearly 90 percent of their salary cap in 2025-26. In that scenario, Brown would not have control over his destiny in any form just a year or two into a five-year extension if the Celtics decide to deal him then.

So how can Brown combat this? Holding out for a player option in year five is one way to increase his long-term flexibility. One other intriguing aspect to consider though if neither side is willing to give in on that front is the supermax structure itself.

Brown’s next deal will kick in after eight seasons of NBA experience. Without the supermax, he is eligible for just 30 percent of the salary cap if he were to hit free agency. However, Brown will gain 10 years of NBA experience by the summer of 2026 and at that point he will be eligible for 35 percent of the salary cap (equal to the supermax) in a new deal regardless of his qualifications.

The question Brown and his camp will need to answer to a degree is whether he values that future flexibility enough to give up the long-term security and tens of millions that would come with a supermax from Boston this summer. In theory, he could play hardball with Boston and bet on himself if he isn’t getting the terms he wants from the team (fifth-year player option, trade kicker etc.) with their supermax offer.

Putting that type of pressure on the Celtics would force the team into a fascinating conundrum. Danny Ainge gave Jayson Tatum a fifth-year player option five years ago in negotiations but handing out that type of deal for Brown is a far different animal to build a team around with the new CBA. Would the Celtics cave to Brown’s demands to keep him in the short term knowing they would have a big and expensive team-building struggle on their hands later this decade with their cap situation? Or would Brown taking that stance ultimately lead to a stalemate and possibly a trade?

The odds firmly remain in favor of Brown and the Celtics finding common ground on the supermax and reaching a deal since this would be an extreme stance for Brown to take. Still, it’s one to consider when looking at why these negotiations have drawn out longer than expected. Both sides still need each other but they likely want to stay together on their preferred terms.