The Boston Celtics have spent the past two summers shaking up their roster after winning the 2024 NBA championship, but while they've moved on from some important pieces, their biggest move came this July when they traded Jaylen Brown to the rival Philadelphia 76ers for Paul George and picks. 

Celtics fans have been willing to put their full faith in team president Brad Stevens since he built the championship roster, but the Brown trade will put that faith to the ultimate test. That includes owner Bill Chisholm, who detailed how challenging that trade was for him in an interview on the Greg Hill Show on WEEI. 

Chisholm noted that he wasn't sure initially about trading the 2024 Finals MVP, but was convinced by Stevens and his team, whom he called "the best brains in basketball," that it was the best move for the future of the franchise. 

"I truly believe we have the best front office in the NBA, and I think it's a source of advantage for us every day. So I definitely have a level of trust in Brad and his team," Chisholm said. "But man, as a fan, that was tough. I really needed to be convinced to take the fan passion out of it, because I'm a super fan, was tough. I think you have to be a sociopath if you don't worry a little bit about what other fans are going to think. And so, to put all that to the side and just do the job -- step back and realize you have a responsibility to protect and advance the legacy of the Celtics. We've got the best brains in basketball, and this was something they had conviction around. 

"I needed to be convinced, and that's my job, but they did convince me, and we did it, and we did it with conviction. And we'll see where it goes, but we feel good about it. All that stuff is tough. It's really tough. On a personal level, I really like Jaylen as a person, the role he played in the community and, obviously, the role he played on the court will be sorely missed."

While the Celtics believe the Brown trade sets them up better long-term, this upcoming season will determine how many fans view it. As Chisholm noted, it's hard not to care what fans think about a move, especially when it comes to trading a beloved franchise star, and if he thrives in Philly, it won't go over particularly well in Boston. 

The Sixers parlayed the Brown trade into signing LeBron James, and Philadelphia suddenly looks like a legitimate championship contender. The Celtics, meanwhile, are hoping that the return of Jayson Tatum at full strength, the addition of Paul George, and the signing of Mitchell Robinson are enough to elevate them back to contender status despite losing Brown from the roster. 

Fair or not, the team that has more success this year will be considered the winners of that trade. That puts ample pressure on Stevens and Chisholm, who have tried to thread the needle on remaining competitive while also alleviating tax and apron concerns. Ducking an apron or dodging the tax is not something fans care about if the team isn't winning, and if the Celtics spend next season in a tier below their two biggest rivals in New York and Philadelphia, the fans' belief in "the best brains in basketball" will start to wane and frustration will build in Boston. 

The long-term plan is great to talk about, but it's a much tougher sell if you tear down a potential contender -- and help a rival boost their short-term prospects in the process. There will be plenty riding on this season in Boston, but if it does end up being the right gamble, Chisholm will be right to boast about the advantage the Celtics have in their front office. 

Add CBS Sports on Google