Renowned NBA Analyst Discusses a Wild Celtics Take

As teams work through the reality of the new salary cap, veteran NBA analyst Bill Simmons and his father discuss the Boston Celtics and introduce an interesting theory.

In an episode of “The Bill Simmon Podcast”, Bill Simmons Sr. believes that the reigning NBA Champions could cut ties with Jaylen Brown following the team’s inevitable sale. They discuss how the team’s luxury tax and the possibility of an NBA Finals loss could impact Brown’s future in Boston:

Bill Sr: “When (owners) come in from outside of Massachusetts, they come in with … different ideas.”

Bill Jr: “They all wanna do their one thing,And then you end up in the Luka Dončić situation, where you have the new Dallas owners (saying), ‘yeah, let’s trade him!’”

Sr: “If they don’t have deep enough pockets, Brown’s probably on his way out the door.”

Jr: “The tax bill is pretty crazy … I think some of it will depend on what happens in the playoffs … I don’t know what’s gonna happen. You’re gonna have this new owner group paying $6-plus billion. The team — let’s say they don’t win the title — and then they’re looking at a tax bill of $200 million on top of what they just paid.”

This narrative has existed in Boston before the Celtics went up for sale. Fans and media alike have always tried to divide Boston’s wing duo of Brown and Jayson Tatum. The two, who finally won their first NBA Championship in 2024, Boston’s 18th overall, have proven successful and are among the frontrunners for an NBA Finals appearance in 2025. The Celtics haven’t won back-to-back titles since 1969, but the team has a championship roster, so the immediate result would be a panic reaction.

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The financial implications do merit. The NBA salary cap aprons are a daunting task that the entirety of the league is learning to navigate, and with luxury taxes approaching astronomical levels, teams are being punished for stockpiling talent. The Celtics may be in a financial catch-22 and have to choose between the two.

One thing to be taken into consideration is who the potential buyer could be. The Celtics are known as one of the premier basketball teams in NBA history, and any potential owner understands they are not inheriting a license to print money and the team has expectations. The Celtics are built for a run in 2025, and as other contracts are up and some of their team retires, the team will be in a position to sign others, but a lot can happen between now and then.

Both Simmons’ have a point in their team concern, and present a true scenario. The finances and expectations can cause the organization to choose between Jayson Tatum and Jaylen Brown. Does this mean the potential to split will happen? No, but it’s worth looking at as the salary cap rules dictate how teams can sign players.

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