When Jayson Tatum suffered a ruptured Achilles tendon in Game 4 of the Eastern Conference Semifinals, the foreseeable future instantly turned murky for the Boston Celtics and their fans. There was speculation that roster changes would take place this summer, even before Tatum's injury and the C's shortcomings versus the New York Knicks.

Considering that the team's championship prospects will now be considerably lower next season, the question might be about who rather than if.

The Celtics signed most of their players to contract extensions over the last couple of years, forking over large sums of money to Tatum, Jaylen Brown, Jrue Holiday, and Derrick White. They vaulted themselves above the second luxury tax apron to win a second straight championship.

The new ownership group, led by businessman William Chisholm, did not make those initial commitments, however. It could use Tatum's lengthy recovery as an excuse to justify significant payroll cuts.

But how much money would Boston look to dump? If management wishes to have its cake and eat it too, it could try to trade Brown and the $240-plus million he has left on his contract in exchange for solid young players and draft capital.

Bill Simmons, a longtime sports writer, producer, podcaster, and Celtics fan, is sickened that such an outcome is even possible. He decried the system currently in place, which he believes denies a team a fair shot at retaining multiple homegrown stars.

“The players' union, who is always run poorly and always does a bad job with this stuff, and this is the worst thing they’ve ever done because they’ve created a league where you can’t keep Tatum and Brown together,” The Ringer founder said on The Bill Simmons Podcast.

“You can’t keep core people together because you can’t afford to do it. You try to keep the two together, and you can’t keep anyone else around them. So this is just the way it is, and you're going to have these three- to four-year windows, and you’re going to have to just blow it up. This I don’t think is what professional sports is about.

“I think professional sports is about I have these guys; we’ve followed them their whole careers; we drafted them; they showed up, or I’ve watched them go through their prime and aged with them. If we’re just going to be this transactional league now, I don’t think that’s good for anybody.”

Simmons got to watch the 1980s Celtics evolve into a dynasty and retain most of their key players during that span. Times have changed, though.

As things stand now, Boston will pay $238.1 million in luxury taxes during the 2025-26 campaign. That mammoth number could dictate the organization's offseason plans.

Instead of trying to unload Holiday and Porzingis — a difficult task given where they are in their respective careers — the C's could pursue a Jaylen Brown trade. If the 2023 NBA Finals MVP is made available, suitors should line up. Simmons has a specific squad in mind.

While he is strongly against separating a star duo in their prime, the former ESPN employee has a potential proposal: Brown and Holiday to the Houston Rockets for Fred VanVleet, Jabari Smith Jr., Tari Eason, and the No. 10 overall pick in the 2025 NBA Draft. This blockbuster would provide the Celtics with cap relief and could also keep them competitive in the long run.

Though, assuming the Rockets would even agree to disrupt their own infrastructure, it would be extremely difficult for Boston to bid farewell to No. 7. The four-time All-Star has given fans life-lasting memories during his nine years with the team. A split, especially if it is motivated by financial factors, could leave excruciating emotional scars.

Boston built a sturdy foundation through the draft, the “right way” as some might call it and then surrounded its pillars with valuable glue-guys who helped hang up a record-breaking 18th championship banner. But as this group could soon learn, the cost for glory is higher than ever.