The past 72 hours since the Boston Celtics were eliminated from the playoffs have been a vortex of emotions, conversations and lack of sleep for Brad Stevens.

The team’s president of basketball operations is fully aware there are a lot of questions for him and the front office as the Celtics embark on an offseason that will be replete with challenges that were both expected and unexpected entering this season.

“I know there will be a lot of questions about what’s next,” Stevens said during his season-ending news conference on Monday. “At the end of the day, I think that will all be driven by the same thing that’s always driven us and that’s ‘How do we get ourselves in the mix to compete for championships best?’”

Contending, though, will be harder than it’s ever been for the Celtics during the Jayson Tatum-Jaylen Brown era, and certainly under Stevens’ guidance. 

Boston faces two glaring issues: Superstar Jayson Tatum is set to miss most of the next season because of a devastating torn Achilles tendon he suffered in a Game 4 loss to the New York Knicks; and the Celtics face a slew of tough personnel decisions, roster moves and financial penalties because of their cap situation.

“The next time Jayson Tatum plays — if we assume he’ll miss all of 2025 — this team will be so drastically different,” Fox Sports’ Nick Wright said Monday on “First Things First”.

With Boston’s payroll for next season on track to come in around $225 million, next year’s tax bill would be at almost $280 million. The combined potential $500 million total price tag would be a league record under the current highly restrictive Collective Bargaining Agreement.

It is unclear whether the team’s incoming ownership will want to keep paying those hefty penalties after agreeing to a purchase in March expected to have a final price of a minimum of $6.1 billion. If they don’t, that means they’ll have to part ways with, likely, multiple players from their 2024 title team. 

“I know they’re going to be trimming salaries,” Wright said. “If I were a Celtics fan, I would just be hoping that, someway, the next time Jayson Tatum takes the court, Jaylen Browns and Derrick White are still his teammates, and I don’t know if that’s possible.”

To make that possible, Boston would certainly have to trade Jrue Holiday, Kristaps Porzingis and Sam Hauser. Holiday is set to make $104 million over the next three seasons. Porzingis has one year left on his deal, at $30.7 million. And Hauser is under contract for three-years, $35 million. While Porzingis’s and Hauser’s deals may not seem overly expensive, they cost more than face value because of the penalties the Celtics have to pay for being over the 2nd apron. 

“If they were to just trade Sam Hauser, it would save them $62 million because his $10 million contract costs them $50 million in penalties,” Wright said. 

He’s speaking in estimations, but the sentiment is clear. Boston is in a bad spot.

Similar penalties would be incurred if they wanted to bring back free-agents Al Horford and Luke Kornet. ESPN reported for every $3 million dollars Boston spends, another $25 million would be tacked on per person. Simply put, if Horford, for some reason, agreed to a one-year, $3 million deal, it would cost the team $28 million total. 

Another issue for Boston is that the Brooklyn Nets and Detroit Pistons are really the only two teams who have cap space this offseason. So, it will be tough to just completely absolve their problems as those teams may ask for heavy draft capital to take on Boston’s big-money contracts. 

“The next time Jayson Tatum plays — if we assume he’ll miss all of 2025 — this team will be so drastically different,” Wright said.

Stevens, the general manaager, mostly declined to provide detail about what will go into that process, saying that he would have more to say on it around the NBA draft. But he did acknowledge that it’s unclear whether so-called championship windows are becoming smaller because of the current CBA.

“That’s a good question. I don’t know,” Stevens said. “I think certainly it is more challenging in certain circumstances for sure.”

He also was clear that even though other factors like Jaylen Brown managing what Stevens confirmed is a partially torn meniscus in his right knee, or Kristaps Porzingis dealing with “post-virus syndrome” didn’t prevent Boston from avoiding becoming the sixth straight defending champion not to make it out of the second round the following season.

“I’d rather talk about the CBA and all that crap,” Stevens joked. “The reality is we blew the first two games (against New York), and that’s why we put ourselves in a tough spot. … That’s not on any one person. It’s not out of maliciousness. It’s not out of a bad decision. It’s not bad luck. It’s we had an opportunity to win those first two home games and we put ourselves behind the 8-ball.”

As for the outlook going forward for Brown and Porzingis, Stevens said he is hopeful that absences away from the court won’t be extended.

He said Brown conveyed to him that his knee felt better by the end of New York series, and that he’s encouraged by Porzingis’ plans to play for Latvia at EuroBasket in August.

He also has confidence that Brown can play whatever role is needed next season during Tatum’s absence.

“Those guys have been the core parts of this program for a while. So, there’s no question about that,” Stevens said. “Those guys, they’ve achieved so much. And certainly deserve all the recognition and praise and accolades they get. But, yeah, that’s a huge part of us being the best version of ourselves.”

The Associated Press contributed to this report.

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