Celtics' new ownership group already faces a difficult task

Wyc Grousbeck and company have agreed to sell the Boston Celtics to a group led by an area native, venture capitalist Bill Chisholm, at a record-setting valuation of $6.1 billion, per ESPN's Shams Charania.

Chisholm immediately finds himself in an awkward situation.

On the one hand, the Celtics are the NBA's defending champions. Led by Jayson Tatum and Jaylen Brown, they captured their record 18th championship last season, and their title defense, at least in the regular season, has been as impressive as any in recent memory. They can absolutely win it all again this season.

Chisholm now owns the most successful franchise in league history and could pad his advantage by June.

On the other hand, a massive tax bill comes due next season. It is the reason the ownership group led by Grousbeck and Stephen Pagliuca opened bidding for the team. According to ESPN's Bobby Marks, payroll and tax penalties could cost the Celtics close to another record of $500 million for the 2025-26 season.

This is what happens when everyone in the starting lineup is owed more than $28 million next season. This past summer, Tatum signed the richest contract in NBA history, surpassing the deal Brown signed in 2023. Jrue Holiday, Kristaps Porziņģis and Derrick White have all signed extensions since joining Boston.

It is a poorly kept secret that Holiday could find himself on the trading block at the end of the season. He is owed $104.4 million through the 2027-28 campaign. Shedding that salary would exponentially save Boston on its luxury tax bill, maybe even enough to make the team profitable for Chisholm next season.

The Celtics have Payton Pritchard as a reserve guard waiting in the wings, and they could remain competitive with him in place of Holiday, though the roster would be decidedly worse. However they shed salary, parting with Porziņģis or White or any high salary will be making the team less talented.

So Chisholm is faced with the difficult task of purchasing a potential back-to-back champion and immediately making them worse. It is a tough spot, no matter how much fans understand the finances.

There is another way, though: Spend the damn money.

Purchasing the Celtics for $6.1 billion, only to trade one of your best players, is like buying a Ferrari, only to put a governor on the engine. What is the point? People presumably purchase pro sports teams to win titles and be the toast of a town, not to make the team worse and immediately become the city's enemy.

The Celtics' ownership group earned $121 million for the 2022-23 season, when their payroll was closer to $200 million, according to Forbes. That operating income surely rose last year, when one of the league's most recognizable brands received a championship boost. This — and probably more — is how much Chisholm's group can hope to retrieve on an annual basis, at least once they get their payroll in order.

Grousbeck, Pagliuca and their group also bought the team for $360 million in 2002, which means they received 17 times their investment in less than a quarter-century. This is what happens to professional sports teams. They increase in value and have since their inception. This is what Chisholm can bank on.

In the meantime he has to decide how quickly he wants to turn Boston into his next cash cow. This is not a short-term investment, so why not take a long view, especially if the Celtics manage to repeat in June. If Boston fails to win this season, the new ownership group will have a built-in excuse to alter the roster.

Conversely, though, the Celtics could soon be looking to become the first three-peat champion since Shaquille O'Neal and Kobe Bryant's Los Angeles Lakers of the early 2000s. That is a stamp that lasts forever, and the Lakers are still reaping the benefits of that brand equity more than two decades later.

How could Chisholm possibly take that away, to spite the fans, just to save a couple hundred million in the short-term, when the alternative is all the glory for which he has agreed to pay the $6.1 billion.

No pressure to win this year, by the way, Boston.