BRIGHTON — “First is Derrick White, second is Jrue Holiday, and third is Kristaps Porzingis.” That was Bill Chisholm’s response when asked about the Boston Celtics’ summer of selling.
Just over one calendar year since the Celtics brought home Banner 18, that squad is all but gone. Some of the core pieces remain in place—Jayson Tatum, Jaylen Brown, Derrick White, Payton Pritchard, and Sam Hauser—but nearly as many have been shipped out in a single offseason.
Boston traded Jrue Holiday to the Portland Trail Blazers and Kristaps Porzingis to the Atlanta Hawks. Luke Kornet left, signing a deal with the San Antonio Spurs, and Al Horford already has one foot out the door of TD Garden (and the other about to step through Chase Center in San Francisco).
Celtics trades were made with the future in mind
Combined with Tatum’s Achilles injury, the 2025 summer months have been one of the most devastating stretches in recent Celtics memory.
But it’s all according to plan. And the three players Chisholm listed are all past examples of said plan.
“If you go back to the Derrick White trades, the Porzingis or Holiday trades, when they came here, those wouldn't be able to happen if you're over the second apron, because you can't aggregate contracts,” said Brad Stevens, the Celtics’ President of Basketball Operations. “You can't take more money back than you send out, right?
“So, you have to give yourself the flexibility and opportunity to jump at the right deals. You don't always know when those are gonna present themselves. So the second apron was the key.”
Boston achieved its goal of getting under the second apron. They now sit roughly $7.8 million below that line (and roughly $4 million above the first apron).
And new owners or not, ditching players with the goal of avoiding second-apron penalties was always going to be a top priority for the Celtics this summer.
“Those moves or this type of movement would have happened whether or not the team sold,” said Wyc Grousbeck. “I was on the committee that really wrote these new rules and negotiated them with the players. So, we wrote them together with the players to make it much more tough to just go and buy a championship.”
Grousbeck, who was the lead owner in Boston from 2002 to 2025, still owns some stakes in the Celtics as part of Chisholm’s group. He always knew changes were coming this summer.
Yet, while money was the front-facing issue the Celtics tried to fix this summer, flexibility was the true intent. Getting below the second apron simply opens up more opportunities for Boston to make franchise-altering trades moving forward.
An easy question to ask could be, ‘Why trade players just to make more trades down the line? Why not just keep the players who were on the roster?’ And though having Holiday and Porzingis on the squad heading into next year, the answer isn’t that simple.
Holiday isn’t getting any younger, and Porzingis’ health concerns and impending contractual needs are a major question mark. And Chisholm wants to do more than win right now.
“My goal and my high-level direction to Brad and team is let's do whatever we can to win championships and win banners and raise as many as we can, both in the near-term, but also in the medium to the long-term as well,” Chisholm said. “So definitely taking that approach and that flexibility that Brad talks about, I think that's paramount to doing that.
“But ultimately, we're going to do everything we can to win, and that’s job number one. And, not just win games – win championships.”
Championships come at a cost. Buying championships may be more difficult, as Grousbeck noted, in accordance with the new CBA, but they’re certainly not free. Boston’s trade-filled offseason is evidence of that—the price of a title.
But for all of the moves made to duck the second apron, getting below the tax entirely isn’t a directive. Saving money could be a goal by the deadline, but the Celtics want to give their current group a real chance to compete.
“Let's see what this team looks like,” said Stevens. “Let's put our very best foot forward. Let's let Joe, the staff, the players, let's all work to maximize ourselves, and with an attitude of no ceilings and no limitations, and go after it. And we'll evaluate the roster like we always will as the year goes on. But there's no tax goal. There's nothing that's set in stone that we have to get to a certain level.”
The Celtics are setting themselves up to compete for years. Tatum and Jaylen Brown will be at the forefront, with Derrick White and Payton Pritchard right behind them.
Now, under the second apron, they have room to give them more help. And if that trade opportunity presents itself, they’ll be ready.
“We're playing for the flexibility to do that kind of thing,” Chisholm. “And when the moment is right to do that, we're going to do it.”