One Element That Could Make This Summer a Little More Interesting for Brad Stevens

There's a bit of uncertainty around the Boston Celtics, at least when it comes to the rest of the league, that could make this an even busier summer for Brad Stevens

Sep 25, 2025; Boston, MA, USA; Boston Celtics president of basketball operations Brad Stevens speaks during a press conference at the Auerbach Center. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

Brad Stevens has been running the Boston Celtics for five years, and he’s gone through a lot of changes in that time. 

He hired Ime Udoka and then suspended and fired him after his scandal. He then elevated a relative unknown, at least as far as coaching, in Joe Mazzulla, which has been a wild ride. He remade the roster under two different collective bargaining agreements, building and then dismantling a champion under different sets of rules. And now he has a new owner. 

The word that comes to mind here is “tumultuous,” but it hasn’t been chaotic enough to make that word feel right about what Stevens has done. Maybe it’s because Stevens has a calm demeanor about just about everything. But that doesn’t mean things are easy. 

The ownership element is a new wrinkle not just for Stevens, but for the whole league. Bill Chisholm has officially been the team owner for about 10 months at this point, which isn’t long enough for anyone in the league to truly get a read on him. 

Feb 6, 2026; Boston, Massachusetts, USA; Boston Celtics owner Bill Chisholm cheers during the second half against the Miami Heat at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

One one hand, Chisholm’s brief ownership has led to a series of trades to get Boston under the luxury tax line. On the other, any team facing Boston’s second apron penalties would have made similar moves.  

“This type of move would have happened whether or not the team was sold,” former primary owner (now a minority owner) Wyc Grousbeck said last September. “I foreshadowed this before the sale that you go up two years, maybe at most three and then you got to come back down. My prediction was you are going to see that for the next 40 years. As long as these rules are in the league, teams are going to pop up as best they can and then they are going to be so strangled on purpose, they are going to come back then.”

But actions speak louder than words, and that's what NBA teams see. For Stevens and his front office, the actions tell a story: Boston is resetting its repeater tax. The question Stevens has to answer for rival executives is whether that's just a fortuitous side effect of available moves, or whether Chisholm is beating down on them from above. 

Rival GMs are vultures. If they smell anything resembling the death throes of a formerly good team, they're going to investigate. The Celtics have been believable in their insistence that this is just good planning in a tough new era. 

“We [will] all meet and sit down and get together and determine kind of the best course of action for building the best team that we can that's also sustainable over a long period,” Stevens said in his postseason press conference. “The one thing, as frustrating as last summer was for all of us, because we were in it with regard to those aprons and the CBA, and we needed to give ourselves more flexibility to create a longer window.”

The Celtics are still good, but that's not stopping the pride of opposing lions from making a run at them to see if they're weak enough to succumb. An opposing executive has to look at Boston’s new ownership and wonder if Stevens doth protest too much when it comes to the motivations behind their moves. Add Jaylen Brown’s Twitch stream to the mix and it’s no wonder Brown’s name has been floated in rumors. 

In a way, the league is run by a bunch of Jordan Pooles because every front office has to shoot their shots at all times. When Brown presents a certain attitude online, intentionally or not, it has to raise some eyebrows around the league. Looking at it from an opposition perspective, I see a team that worked hard to get under the tax line blow a first-round series, and then their All-NBA guard acting a little cavalier about the whole thing on the internet. Of course I’m calling Stevens and asking what’s up. Maybe I’m even being coy about it and starting the conversation complaining about my boss to see if Brad will do the same. 

Okay, maybe the two-time Executive of the Year isn’t falling for sixth grade reverse psychology, but the point remains that the “under new ownership” sign is still hanging on the franchise, so this is going to fuel a lot of speculation until the league can suss out what Chisholm’s motivations are and what kind of pressure he’s putting on the team.

“I have to be accountable here, and I signed up for that,” Chisholm said when he was introduced last September. “I thought long and hard about it. This took a year, that’s a lot of time to think about it. And yeah, I believe I’m up for that challenge. But I know it'll be challenging at times. And I thought about that. My family thought about that, and you know, we're all in.”

I believe that, but there's no doubt the league will test that. And Stevens wouldn’t be doing his job if he didn’t listen, because you never know when something that makes sense springs out of a fountain of hogwash.