There are many people in the NBA world who were shocked to see the Celtics re-sign Jaylen Brown to a supermax contract extension worth $304 million over the next five years.

The NBA’s new collective bargaining agreement will make it difficult for Boston to continue building a championship contending team as they’ve limited themselves to two players utilizing upwards of 70 percent of the cap between Brown and Jayson Tatum, who’ll be ready for a supermax of his own next summer.

Jamaal Aflatooni of the And One Hoops Podcast believes the Celtics will ultimately regret signing Brown to this supermax extension in the immediate future and down the road.

“The NBA has now implemented a two-tier luxury tax system, whereby if you exceed these tiers over the tax line, teams are penalized by not having the ability to use their full midlevel exception to sign free agents and they actually lose their ability to trade first round draft picks seven years out to the future. By signing Brown to the supermax extension in addition to the likely extensions they’re going to need to offer to guys like Kristaps Porzingis, Jayson Tatum. The point is, they’re going to be entering that second tier.”

Team owner Wyc Grousbeck has been consistent with his stance to spend money, giving GM Brad Stevens the “green light” to do so in this window of time with both Brown and Tatum.

Aflatooni also gets into how this contract will make it challenging for the Celtics to move if they decide to trade Brown, saying that teams will be less likely to add large contracts due to having less roster flexibility that comes with it under the new CBA.

It’s worth mentioning that there is a trade kicker linked to Brown, so if Boston does trade him, they’ll be the ones responsible for paying the kicker if he’s traded. 

The salary cap should continue to increase every year, which means we’re going to see contracts like Brown’s become the norm, it just so happens that he’s the first one to sign the deal.

I don’t think the Celtics will regret signing Brown to a supermax contract but realistically, Boston’s window might not be open for too much longer.

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