Well, that went poorly. Just two nights after the Boston Celtics showed signs of life in the wake of Jayson Tatum suffering a ruptured Achilles with a 25-point blowout victory in Game 5, the Celtics fell flat on their face and got mopped by the New York Knicks in Game 6. With a 119-81 loss, Boston now heads into an offseason full of uncertainty, which is a crushing result considering the championship aspirations this team had just one week ago.

The C's have some serious questions to answer this offseason. There was always the big question of whether it'd be sustainable to keep this team intact past this season given the massive financial and roster building penalties that would be imposed upon them as a repeat luxury tax offender in the second apron, and that question looms larger now that this team didn't win a title, and will presumably be without Tatum for most, if not all, of the 2025-26 campaign.

All options are on the table for Brad Stevens and the Celtics front office, and it seems like some serious changes are in store this offseason. But what are they, and how can the team manage to remain a championship contender amid this period of change? That's the question that Stevens will set out to answer this offseason, and there are several different avenues he could ultimately end up pursuing.

How can the Celtics recover from playoff elimination?

Boston Celtics players watch from the bench during the end of the fourth quarter of game six in the second round of the 2025 NBA Playoffs against the New York Knicks at Madison Square Garden.
Mandatory Credit: Brad Penner-Imagn Images

Boston's 2024-25 season will end up going down as a missed opportunity. After dominating on their way to a championship last year, the Celtics brought back virtually the same team, and while they weren't as convincing during the regular season, the expectation was still that the path through the Finals ran through them. Even before Tatum's injury, it was clear that wasn't the case.

The C's old struggles in crunch time returned against the Knicks, and it resulted in them throwing away three games they should have won. It may not have mattered considering Tatum's injury, but if Boston protects a pair of 20-point leads in Games 1 and 2, and a 14-point lead in Game 4, they are in the Eastern Conference Finals right now.

Instead, they enter the offseason far earlier than expected, and it appears as if changes are on their way, with Tatum's injury expediting the process. Boston needs to figure out if they want to contend for a title next season, or take a bridge year and reset their roster. Given the state of the roster, either path is viable, but one is clearly better than the other (more that in a minute).

What the Celtics cannot do is run things back with the same roster. Yes, it will be tough to break this team up, but at the end of the day, they put themselves in a situation they could not dig themselves out of against the Knicks. Suffering the wrath of the NBA's new second apron penalties is not worth it if this team could not get past a New York team they destroyed during the regular season.

The obvious main goal of the offseason is to get under the second apron. Right off the bat, Kristaps Porzingis, Jrue Holiday, and Sam Hauser stand out as trade candidates for the front office. Holiday can be replaced in the rotation by Payton Pritchard, and Baylor Scheierman proved he can fill Hauser's role as a three-point ace off the bench down the stretch of the regular season.

Porzingis is the wild card for a couple of reasons. Boston's big man rotation will likely be much different next season, as both Al Horford and Luke Kornet are free agents. Teams will also likely be concerned by Porzingis' health issues that plagued him throughout the Celtics postseason run. If he doesn't earn a clean bill of health this offseason, that will make trading him tricky.

Moving at least Holiday and Hauser should get the C's under the second apron, although it would ultimately depend on what they manage to get back in return for them. That seems like the most plausible starting point for Boston, with a potential Porzingis trade being in the cards. However, there's a bigger move that could be made, although it seems far less likely.

No matter what the Celtics do, the second apron is always going to be an issue for them during this era because more than half of their salary cap space is being allocated to Tatum and Jaylen Brown. As we already mentioned, Tatum is likely out for the 2025-26 campaign, so could Stevens opt to reset the roster by moving Brown in a blockbuster trade this offseason, and instead focus fully on building around Tatum?

The most popular idea floated around would see Boston build a trade package around Brown in an effort to trade with the Dallas Mavericks for the No. 1 overall pick in the 2025 NBA draft, which gives them the right to draft star Duke basketball prospect Cooper Flagg. This would see the Celtics clear up a massive amount of cap space, while also gaining a potential superstar in Flagg on a cheap rookie contract.

There are several major risks when it comes to this option. While Brown has his flaws, he is a top 10-15 player in the league, and even though Game 6 didn't go Boston's way, he has proved he can lead this team with Tatum out. That is extremely important considering Tatum's pending absence, as that means Brown will be tasked with leading the way.

Established talent is better than potential talent, while Flagg looks like the second coming of Tatum and has ties to the New England area, there's no guarantee he lives up to his potential. Tatum and Brown make a lot of money, but there's a reason for that; they are a championship-caliber duo, and for that reason, breaking them up seems unlikely.

Even when Tatum comes back, he's likely going to be rusty, meaning his team will have to pick up the slack in the meantime, which is where Brown once again comes into play. Moving Brown could conceivably allow Stevens to keep the rest of the front office intact, but is that what they want? Guys like Horford and Holiday aren't exactly young guns anymore, and again, the path to title contention seems unlikely next season with Tatum out.

The most viable option seems to be the option that best suits the team moving forward. Move on from Holiday, Hauser, and ideally Porzingis, while working to build the roster around Tatum, Brown, and Derrick White. Clear the salary cap out for the upcoming season so that when Tatum returns in the 2026-27 campaign, the Celtics can load up once again and build their next title team after their quest to repeat as champions this year came up short.

If Stevens and the front office play their cards right this offseason, this won't be the end of an era, but rather a temporary roadblock that will make the team's next championship even sweeter.