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Windhorst shares the terrifying contract fear that drove Jaylen Brown trade

The Celtics' trade return for Jaylen Brown was perceived as low, but Boston was convinced that his looming contract extension was only going to make things worse.
Feb 4, 2025; Cleveland, Ohio, USA; Boston Celtics guard Jaylen Brown (7) reacts in the first quarter against the Cleveland Cavaliers at Rocket Mortgage FieldHouse. Mandatory Credit: David Richard-Imagn Images
Feb 4, 2025; Cleveland, Ohio, USA; Boston Celtics guard Jaylen Brown (7) reacts in the first quarter against the Cleveland Cavaliers at Rocket Mortgage FieldHouse. Mandatory Credit: David Richard-Imagn Images | USA TODAY Sports via Reuters Connect

No matter how you slice it, Jaylen Brown’s contract was a big part of the reason he got traded. The Celtics insist they wanted optionality going forward, and spending 70% of the cap on two players simply isn’t good business in the current NBA economy. Brad Stevens and his team made a difficult decision that the team was better off being built without Brown.

Sure, there were some issues with Brown’s play and impact, but that was just compared to his contract. The Cs think they can get more return by spending that cap space elsewhere. They were urged to act more quickly, with JB coming off a career year and with three years left on his deal, but the return still seemed underwhelming.

Brown's contract close to a tipping point

Part of that was that the league has already caught up to the reality of the CBA and what it means for players on supermax contracts, especially ones who aren’t the elite of the elite, like Jaylen. But as much as the return may have underwhelmed fans, the team believed it was only going to get worse, largely because Brown was about to be eligible for a two-year, $140+ million extension.

He was going to want that deal, that would have had him making over $320 million in the next five seasons, and the Celtics wanted no part of it. According to Brian Windhorst on First Take:

“In the case of Jaylen Brown, the Celtics believed that Jaylen Brown was going to be seeking a contract extension this summer. And if they gave him that extension, not only did they think they weren’t getting $57M value, but then he’d become untradeable.”

It’s a harsh reality, but that’s the situation that the Celtics were facing. Teams are quickly realizing that in the modern NBA, you need deep teams with diverse star talent up and down the roster. Max and supermax contracts for guys playing complementary roles are a death sentence for team-building. The Celtics were one of the first teams to face this truth, and they tried their best to sell high.

Celtics did the best they could in this NBA market

They extracted valuable draft picks and a player who is overpaid, but still very good, and a year closer to expiring in Paul George. Boston was worried about getting trapped with most of their resources going towards a Jayson Tatum-Jaylen Brown pairing that simply may not be enough. 

If the money gets even bigger, and the rest of the league starts to feel the same way, the price for Brown would only have gone down. The Celtics didn’t want to get into a contract impasse with Brown, and they didn’t want to get stuck with a deal that they didn’t feel would return value. Add in the fact that Jaylen was influencing the market, and Stevens’ hands were tied.

He did what he felt was best for the Celtics and made the proactive move that he felt was necessary to push this team into the next generation. It’s still a massive gamble, and the only way it will be vindicated is by winning, but the logic behind the deal is at least starting to make more and more sense.

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