The Biggest Question the Boston Celtics Still Haven't Answered This Offseason

The Celtics are operating in a place no team has before, so they might not even know the answer to the question

Sep 29, 2025; Boston, MA, USA; Boston Celtics president of basketball operations Brad Stevens talks to reporters during media day at the Auerbach Center. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

Brad Stevens and the Boston Celtics are guinea pigs. They willingly accepted that role when they handed out big extensions to Kristaps Porzingis and Jrue Holiday a few seasons ago. 

When the second apron came into existence, the Celtics were the first team to test its limits, feel its sting, and start charting a path through the financial madness. Fans on the outside aren’t conditioned enough to the new system yet, so while Stevens and his team act like part Lewis and Clark and part Dr. Emmett Brown, fans are left guessing why they're making some of these confusing moves.

Trading Jaylen Brown for Paul George and picks is just the latest one. 

“It was a really hard call. I’m not saying it was the right call,” Stevens said when he explained the move last month. “We wanted to stay good and we wanted to add more optionality.”

Staying good and creating more options is great, but it doesn’t answer one big remaining question. 

What’s next? 

The Celtics are acting like a team scrambling to make minimum payments on a big credit card bill. They seem to be lining up their ducks, but what happens once they're in a row? 

“There were a couple of paths, right? A big swing or not,” Stevens said. “I thought our path to getting what we ultimately wanted to do, we probably looked more like the last couple of years, and whatever changes we needed to make were not obvious. To do a deal like Jaylen requires the right amount of talent and what we deemed to be the right assets coming back … I had a lot of time to study, think and use the expertise of the people in our building, and try to figure out how best to move forward.”

Most teams have, at least outwardly, a clearer vision for the future. When teams start structuring contracts to have them all expire at the same time, we can scan through the contracts to find out which free agent they're angling for. When teams start blatantly tanking, we know what players they're hoping to draft. 

With the Celtics, we have a more theoretical view of things. Paul George will be on an expiring contract next summer and the Celtics have picked up two premium picks to go along with him. They can use that combination to swing a trade for someone to pair with Tatum, or multiple players to help accentuate Tatum as the lone star. 

We can certainly speculate by looking at the most expensive teams in the league. The Denver Nuggets and Orlando Magic are in the second apron right now. The OKC Thunder are only a couple million away right now and Shai Gilgeous-Alexander gets a $23 million raise in 2027-28. The Knicks have already made decisions to avoid the second apron (thank you for Mitchell Robinson, by the way) and more are coming. 

But these are all guesses without any clear vision. They are sharks swimming in waters where food might be, but they don’t seem to be locked in on any prey. This season, another gap year of sorts, could be one where they find some of those answers. 

“We have both really good young depth, some guys that I think will not only be good in the near term but just continue to get better,” Stevens said. “Paul's contract … how it times up, that will give us optionality, not only in adding to our team but also retaining some of our team, which I think is important.”

The Celtics have already handed out contracts to Neemias Queta, Jordan Walsh, and Ron Harper Jr., so that's one step they’ve taken. We know Tatum isn’t going anywhere … at least not anytime soon … so now how do they make this team a true contender?

The Celtics are now trying to land their play while operating under visual flight rules. There's a landing strip somewhere out there, but they're going to have to wait and see before figuring out their next step. They are creating the map for everyone else in the league to follow. 

It’s one that hopes to avoid the very intentional traps set for teams in the current CBA. Boston was a very expensive team, and they were supposed to be destroyed because of it. The CBA is a sort of Bond villain, and Stevens is the guy in the tuxedo making puns and somehow using a cufflink to get out of trouble. It’s a very “fly by the seat of your pants” kind of situation. 

What’s next? The Celtics might not even know.