Celtics May Look to Cooper Flagg as Jayson Tatum Replacement Under New Owner

ESPN Names Tatum Best NBA Comp For Flagg

If the Celtics can replace one high-paid player with another making less money but of comparable abilities, they could find a solution to their second-apron problem. That player could be Cooper Flagg, the Duke star and consensus No. 1 pick in the upcoming NBA draft. According to an ESPN analysis based on interviews with NBA front office executives and scouts, the NBA player in his prime most comparable to Flagg is Celtics superstar Jayson Tatum.

Entering next season, the Celtics are looking at exceeding the second apron by $18 million. Using calculations by ESPN’s Tim Bontemps, that would put the Celtics total player expenditures including the financial penalties for exceeding the second apron line at more than $500 million.

Celtics outgoing owner Wyc Grousbeck, who authorized team president of basketball operations Brad Stevens to cross the second apron line in assembling the powerhouse team that cruised to the 2023-2024 NBA championship, said in a recent interview with Boston radio station WEEI, “Because you have to navigate because you can’t stay in the second apron, nobody will, I predict, for the next 40 years of the CBA, no one is going to stay in the second apron more than two years.”

Now the Celtics have a new owner — private equity financier and Massachusetts native, and self-proclaimed lifelong Celtics fan William “Bill” Chisolm.

After leading an investment group that bought the team in a sale announced March 20 for a record $6.1 billion, Chisolm declared “I want to raise banners. I want to raise them now, and I want to raise them in the future as well.”

‘Billy Banners’ Faces Need to Trim Celtics Payroll

That may have earned him the nickname “Billy Banners” among Celtics fans, but how realistic is it, given Grousbeck’s prediction that no team can stay in the second apron for more than a couple of years? Chisolm will likely have no choice but to trim payroll — and the quickest way to do that would be to deal away the Celtics’ highest-paid player, Jayson Tatum.

Last offseason, Tatum qualified to sign a type of contract known under the NBA Collective Bargaining Agreement as a Designated Veteran Player Extension, better known as a “SuperMax.” The details are complex, but the bottom line is that starting in the 2025-2026 season, Tatum’s salary jumps by nearly $20 million, to $54.1 million. Tatum’s pay then goes up each year until the final year of his SuperMax deal, when if he exercised his player option, Tatum would collect an astounding $71.45 million for a single season of basketball.

According to a plan laid out by Ringer founder Bill Simmons, the Celtics could make a move to acquire Flagg once his four-year rookie contract is up. At that point, Flagg would not be eligible for a SuperMax contract, meaning he would cost considerably less than Tatum. But is he really a replacement for the future Hall of Famer, who also played his “one and done” year of college ball at Duke?

Jazz, Hornets, Wizards Favored to Draft Flagg

“Tatum’s balanced, high-volume offensive profile with the Celtics shows how Flagg could grow into a similar role — particularly if his future team guides him toward high usage,” wrote ESPN analyst Jeremy Woo. “Flagg is a more accomplished playmaker for others, more than doubling Tatum’s assists per game at Duke, and the passing figures to be more central to his offensive value in the NBA. Flagg’s shot selection is a bit more team-friendly, but while he has made strides creating his own shot in the half court, Tatum was more polished.”

Of course, whether the Celtics can acquire Flagg before Tatum’s SuperMax contract expires is to some degree up to the team that drafts him. According to FanDuel odds, the Utah Jazz, Washington Wizards and Charlotte Hornets are tri-favorites at +500 to land Flagg with the No. 1 pick coming out of the NBA draft lottery.