Jaylen Brown has three years and about $183 million left on a 5-year contract he signed in July of 2023. It was a controversial deal at the time, but Brown was headed to free agency the next year and the Celtics knew they needed to keep him.

Fast forward three years later and Jaylen Brown will once again be eligible to sign a contract extension on July 26th. This deal would tack on an additional two years and an estimated $142 million to his deal.

That in total would have Brown on Boston’s books for the next five years at $325 million and he would be 34-years-old when the deal runs out.

Last summer, the Phoenix Suns were presented a very similar situation with Devin Booker. Booker, like Brown, had three years left on a super-max extension he signed in 2022 and was eligible to add two more years on to his deal. The Suns did offer him that extension, which was reported at $145 million but based on future cap projections, Spotrac estimates that it will come in at $132 million. No matter what the deal is worth, Booker is going to make a lot of money.

Brown just had his best NBA season this past year and, to me, is a better player than Booker is. If Brown is going to sign a new deal, it is going to be a max.

With that said, I am in no rush to extend him.

There are reasons for the Celtics to ink Brown to an extension.

Number one, it would keep him happy. Earlier this week, Brown said on his Twitch stream that he wants to be in Boston for the next ten years. No one turns down the 35% super max and Brown is no different. If the Celtics were to offer him a max extension, I am very confident that Brown would sign it.

Number two, and the far more compelling reason, is that Jaylen Brown is a great player who the Celtics should want to keep around for a really long time. I know he didn’t have a great series against the 76ers but he was so awesome this season. He averaged career highs in points (28.7) and assists (5.1) in the regular season while being the best player on a team that won 56 games without Jayson Tatum.

On the other hand, why should Boston rush to sign him? As was mentioned, Brown has three years left on his current deal with no player option. Free agency is not lurking like it was back in 2023.

Another aspect of this is that the Celtics have Jayson Tatum. The Suns were backed into a corner with Booker because he is their best player. Phoenix had just traded Kevin Durant and bought-out Bradley Beal — they needed to keep Booker on the team and happy so they paid him.

The Tatum and Brown duo has brought Celtics fans a lot of joy over the years, including a championship, and the Celtics should want to keep them paired together. Extending Brown this summer and Tatum next summer, when he becomes extension eligible, would accomplish that.

However, the Celtics did lose in the first round this season and Brad Stevens talked about how they were not good enough at his end of season press conference on Wednesday.

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— Karan (@ksenguptaa) May 8, 2026

However, I don’t think the Celtics need to rush into signing Brown to a new deal because their team wasn’t good enough this season and locking into this core doesn’t sound like something Brad Stevens is ready to do.