In the city where “almost” has never been good enough, new Celtics owner Bill Chisholm has made it clear, coming second is not acceptable. And among the NBA’s most expensive franchises now under his command, he’s applying early pressure on two of the most important figures in the organization, head coach Joe Mazzulla and All-Star Jaylen Brown.

Backed by a $6.1 billion investment, Chisholm took control of the Celtics just 14 months after they lifted Banner 18. But now, with Jayson Tatum sidelined for the year, a stripped-down roster, and a payroll reset under the league’s new financial rules, the margin for error is gone. The torch has been passed, and the expectations haven’t dipped an inch. Yet behind the bold declarations, even Chisholm himself concedes there’s a weight that comes with inheriting Boston’s empire—pressure he couldn’t entirely mask once the ownership shift accelerated.

The Celtics’ new lead governor wasted no time in making his stance clear. “We’re not playing for second; we’re playing for championships and banners,” Chisholm said to The Globe. “We’re playing for them in the near term, although we obviously had to do some things to get below the second apron. But we’re also playing for them in the medium and long term.” Bill Chisholm’s words aren’t just about optimism, when he says, “You have to do it with talent, you have to do it with leadership,” he’s laying out a blueprint that shifts the Celtics away from simply outspending the competition. 

The NBA’s second apron has made it clear that money alone won’t win titles anymore. Instead, Chisholm is trusting Wyc Grousbeck, Brad Stevens, Rich Gotham, and Joe Mazzulla to lead the franchise through a tougher era. Calling them “the best leaders in the league” is both a vote of confidence and a public expectation. Earlier this month, Boston handed Joe Mazzulla a multi-year contract extension, a move Chisholm had to green-light even before officially assuming full control. 

Meanwhile, with Tatum sidelined, Jaylen Brown steps into the spotlight. The Celtics’ former Finals MVP, a four-time All-Star and 2024 champion, now carries the full weight of a franchise, and the scrutiny that comes with it. Boston legend Bob Ryan didn’t hold back, calling Brown a “very good” player but doubting his ability to anchor a top-tier team. “They’re going to be lucky in that 7–8 mix,” Ryan said. Bob Cousy echoed the sentiment, suggesting Brown may not be the guy to keep Boston at the top. Results matter, and Chisholm is looking forward to leadership to carry more weight than just flashy acquisitions or short-term gambles. 

Chisholm admits pressure after sudden Celtics power shift

Under the original agreement, Wyc Grousbeck was expected  to remain lead governor until 2028. But NBA rules intervened. When the deal was fully funded, Grousbeck’s stake fell below the required 15%, forcing an accelerated handoff of power to Chisholm.

Chisholm admitted the pressure is real. “I’m thrilled, and as a fan am just thankful to have this opportunity, but also to Wyc and his group, because [what they accomplished] is pretty spectacular and it’s a pretty high bar,” Chisholm told the Globe during a joint interview with Grousbeck. “So, I’m feeling the pressure.” Chisholm now leads a franchise in transition. The Celtics are fresh off significant changes with Kristaps Porzingis and Jrue Holiday already gone, payroll slashed by nearly $300 million, and Tatum is recovering from a ruptured Achilles. A contender turned question mark, overnight.

Entering his fourth season, Mazzulla now faces his toughest challenge. A rotation filled with new faces and veteran gaps. And for the first time since taking over, his Celtics aren’t expected to be title favorites. “I’m really excited to see what he does in this kind of environment,” Chisholm said. “I think people will really appreciate what he’s all about. When he doesn’t have the loaded team, what can he do? And I think that’s going to be really interesting, and I have every confidence he’s going to crush it.”

But Chisholm is standing behind his roster. He highlighted Brown, Derrick White, and Payton Pritchard as a core with “real talent that hasn’t been fully realized.” This season is a test for Chisholm’s vision. “The ultimate yardstick is winning championships,” Chisholm said. “Wyc’s got two, and we’re going to get more, and he and I together are going to help drive that.” For Boston banner 19 remains the goal, just with a new blueprint.