Brad Stevens says he has ‘lost sleep’ over Jaylen Brown trade, but the deal gives the Celtics flexibility

In early June, Celtics president of basketball operations Brad Stevens met with star forward Jaylen Brown and had candid conversations about his future with the team. Stevens did not say then that Brown’s Boston tenure was over, but the possibility at least started to crystallize.

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“I told him that if we were to ever trade him,” Stevens said, “that would be a really sad day for me personally.”

On Monday afternoon, Stevens and lead governor Bill Chisholm sat in front of cameras and microphones on the sixth floor of the Auerbach Center, a few hours after the deal to send Brown to the 76ers in exchange for Paul George and four future draft picks was finalized, and the mood was gloomy.

Stevens opened his 45-minute news conference with an eight-minute opening statement, his longest ever. He said he understands the frustration of fans, who are overwhelmingly against this move. He added that his children and Chisholm’s children are sad about Brown’s departure, too.

“Listen, I’ve lost sleep over the fan part of this,” he said. “I get it. There’s a bunch of No. 7 jerseys around. I’m pretty sure I bought a couple. So, I get it. And somebody asked me earlier today, ‘Do you miss coaching?’ I said, ‘I did this week.’ This is not for the faint of heart.”

Putting those emotions aside, Stevens decided to complete this deal that sent Brown to one of the Celtics’ biggest rivals for a package that has been viewed around the NBA as underwhelming.

But Stevens said the Celtics’ frustrating playoff exits the last two seasons made it clear that some change was needed, even if he did not always think it would be this seismic.

A frank assessment of the roster and payroll made Stevens leery of the fact that it was bloated at the top, with Jayson Tatum on a five-year, $314 million contract that runs through 2029-30, and Brown having three years left on his five-year, $285 million deal while also eligible for a two-year, $142 million extension this fall.

“The path looked a little more challenging to me,” Stevens said. “I might be wrong. I’m not going to stand up here and be defensive about that. But the path looked a little bit more challenging with 70 percent of our [salary] cap and such a high percentage of our usage tied into two players.”

Brown’s salary is only about $3 million more than George’s, but he has one more year on his deal even without the looming two-year extension. The Celtics improved their flexibility by adding the four draft picks, including 2028 and 2031 first-round picks that Stevens described as “premium assets.”

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“What we ultimately decided could be right or wrong,” Stevens said. “It’s obviously unpopular, and most people think it will be wrong. There wasn’t one piece that I would say did put us over the top. It was just we went through everything. We assessed everything. We spent a lot of time on it.”

During a Twitch stream from his home last week, Brown said Stevens communicated with him early in the process, but then “out of nowhere, things just went left.” The five-time All-Star and 2024 Finals MVP was frustrated with the lack of respect shown.

Stevens said that he and Brown might have differing views of how the process unfolded, but he hopes to eventually sit down with Brown to talk about the situation.

“If he feels that way, then I’m sorry about that,” Stevens said. “I am, genuinely. Because he’s a meaningful person in all of our lives, and certainly mine.”

The Celtics initially made Brown the centerpiece of their offer for Bucks superstar Giannis Antetokounmpo. When Milwaukee agreed to trade the two-time MVP to the Heat, it appeared Boston would move forward with Tatum and Brown as its cornerstones.

Instead, the Celtics continued to engage in trade discussions involving Brown with multiple teams. Stevens said Monday that the Celtics were not operating with a sense of urgency and would have been comfortable bringing Brown back. They just found a deal that they liked, and even then, there were hard, agonizing conversations.

“The mandate is to win,” Chisholm said. “And this was, Brad and his team came with a recommendation, ‘This is the way we’re going to win.’ And I looked at it and I had the same reaction [as many others]. I was like, ‘Wow, this is, the fan in me, it’s really tough.’ . . . We came to the conclusion — they convinced me this was the best way for us to win. And I got there. I did. But it was hard. It was really hard.”

It was made harder by the fact that Brown was being traded to a rival that came back from a 3-1 series deficit and eliminated the Celtics in the first round of the playoffs two months ago. Stevens revealed Monday that the Celtics and 76ers will play two preseason games this coming season, so there will be six total matchups before the playoffs. For various reasons, it won’t be easy.

“If I was being honest, if that exact deal came from a team out West and you were comparing the two, then you’d probably take the team out West,” Stevens said. “But that’s not the way it would work.”

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