This may sound like I’m being critical, but I’m not. Long-term star injuries for contenders are rightfully watershed moments in NBA thinking, especially regarding team building. How can you not? The same moment happened when Kevin Durant grabbed his leg in Toronto during the 2019 Finals. And given the cascading effect of that injury, we were right to speculate wildly.

Although the Celtics are unlikely to experience the catastrophic post-injury season that Golden State went through, many of the same assumptions apply. The team won’t be contending this upcoming season. Their immediate window is over. Tough questions will have to be asked of the roster. The question for me becomes, can the Boston Celtics use this tragic injury to their benefit in the long run?

Key Assumptions

Those reading this most likely fall under the umbrella of NBA sicko-dom. You follow Keith Smith, you’ve opened Spotrac to check on contracts, and you can list CBA rules off the top of your head. You know, normal people stuff. The average NBA fan has some idea of how the salary cap works, but the motivations of NBA front offices/ownership groups and the avenues to accomplish their goals may be more of a mystery. My first assumption is that most people who wear Celtics hats don’t understand the ramifications of the salary cap.

The worst-kept secret in the NBA is that everybody fears the consequences of the luxury tax. Even Warriors owner Joe Lacob, with a franchise seemingly doubling in value yearly and a line of minority investors in Patagonia quarter-zips around the block, feared the tax. The Boston Celtics hit their tax window perfectly, setting up a two-year run of having Jayson Tatum, Jaylen Brown, Jrue Holiday, Kristaps Porzingis, and Derrick White all paid their worth. That first season resulted in a championship. The second, as we know, was a tragedy. My second assumption is that no matter how these playoffs went, the bill was coming due, and a slash-and-burn salary dumping was coming this offseason.

But the dollar figure is secondary here. What matters most are the restrictions associated with salary cap overages. New ownership will want a clean slate upon which to build a new team instead of being beholden to the transactions of the old regime. This leads us to the number that will define Boston’s offseason.

$19,959,873

The second apron is the word you’ll hear a lot this offseason. That amount you see above is the projected dollar amount Boston needs to cut to get below that figure. The second apron is extremely restrictive for a team that will need to be nimble over the next few seasons.

First and foremost, it stops you from aggregating multiple outgoing salaries together in trades or taking in more money than you send out. As long as they’re above the apron, Boston cannot send out multiple players in a single trade, and their cap number can only decrease in any trade. This, by itself, is very limiting. On top of that, if you spend three out of five years in the second apron, your first-round pick automatically becomes the 30th overall pick. It also limits the future draft picks you can trade.

The goal of this new CBA was to promote parity around the league, spread the talent out, make dynasties harder to form over years, and engage every fan base. When you’re the Boston Celtics, having five players making $28+ million is like walking into a bear den with your pockets full of beef jerky.

Boston’s championship team was $5 million above the second apron, and this year’s team was $4.4 million over. Don’t just take this prediction from me: Wyc Grousbeck, the newly former Celtics owner, said it himself. Since the draft pick penalty rolls over five years, the Celtics would have their first-round picks moved to #30 in several upcoming seasons. They would need to duck the second apron for three consecutive seasons to avoid further penalties.

In short, if the Celtics don’t find a way to shed this money, they’ll be strung up by their ankles trying to improve this roster in the coming years. Jayson Tatum is 27 years old, Jaylen Brown is 28 years old, and the two project to have many great years of basketball ahead of them. This limitation on their roster-building capabilities would be tough to overcome. Now, let’s figure out how Boston can get under this.

One last number to consider here: 13. Boston has to enter the season with at least 13 players to meet the league minimum requirement. As things stand, they have 12 under contract for next year. So all moves will need to keep that target number in mind.

The Jrue Holiday Issue

Jrue is the first and foremost player in these conversations. This season was the first year of a four-year, $134 million extension Holiday signed after the championship run. They wanted to take care of him for the chance at back-to-back titles, but it has been clear he would be one of the first to go, especially as he declines going into his age-35 season.

This article isn’t about speculating who Boston can acquire; you’re all adults capable of working a trade machine. This is about the math needed for a route to cap relief. So here’s the breakdown on what Boston can do to whittle down that $20 million tax overage, starting with Jrue’s $32.4M salary.

Boston must take back at least 80% of Jrue’s salary in a two-team deal. Assuming they can find a deal to take back the minimum, whether one player or multiple, that would be $6.48M in savings. That’s roughly a third of the number needed. It gets even more interesting when you take three-team deals into account. The 80% rule doesn’t have to go all the way around. Boston can send Jrue to one team, then that team can send the 80% of Jrue’s salary to a third team, who can in turn send 80% of THAT salary back to Boston.

If GM Brad Stevens can make a three-team deal work at the minimum amount, Boston could take back a minimum of $20.74M. That would be $11.66M in total savings, more than half of the number needed. Assuming this gets done by acquiring two or more players, that would also put Boston at or above the 13 minimum required players. Now, we’re left with some flexibility and several ways to get the remaining $8.3M off the books.

Remaining Options

I will take a leap here and assume that neither Jayson Tatum nor Jaylen Brown will be dealt. That leaves a few avenues for the remaining money.

First, and most obviously, they can move on from Kristaps Porzingis and his expiring $30.7M salary. If Boston again takes back the minimum salary in a two-team deal, that’s $6.14M in savings. Expanding to a three-team deal, the Celtics could save up to $11M; only taking back $19.7M in the exchange. That could cover the tax amount needed, but something else comes into play: the upcoming draft. Boston owns the 28th and 32nd overall picks, and assuming they draft and keep players at both those slots, that salary would put them back into the apron.

There are avenues to overcome this. Neemias Queta, Xavier Tillman, and Jordan Walsh all have minimum-level deals that could be salary dumped into the cap room of another team, or traded for non-guaranteed contracts that Boston can then waive. But it would be tight and would cut into their 13-player roster minimum.

Another option would be Sam Hauser and his $10M salary. His contract is small enough to be traded into an exception or cap room for teams with cleaner salary sheets. That and some trades involving the minimum deals above would accomplish the task. This would be even tougher to navigate with the player minimums, however. Turning Hauser and one or more others into zero returning players would put extra pressure on a Jrue Holiday trade to include three or more players coming back.

I lean towards Porzingis being the solution here. His expiring deal and dip in play this year make him an obvious candidate. Hauser did have a down year, but he fits the system well and is on the books for four more years. Trading Hauser for other players wouldn’t accomplish much due to the tax problems. So, of the more obvious solutions after Jrue, Kristaps makes the most sense.

However, Porzingis and Hauser aren’t the only solutions to this.

The Nuclear Option

One assumption I’ve made up until this point is that Boston is making these moves with the intention of returning to the fray with the same core after Tatum is healthy. Their star wing pairing, plus Derrick White and Payton Pritchard, can all stay on the roster while they duck the second apron. That would almost certainly make them a playoff team in a weak East next year with Brown, White, Pritchard, and whatever they get back for the above trades.

But there are alternatives. What if Boston looks at Derrick White, about to turn 31 and begin a four-year, $118 million extension, as a potential negative asset by the time Tatum returns? After all, defense-first guards tend to fall off cliffs sooner than expected. Perhaps Boston thinks it can get out of the casino before going bust by trading White to a more immediate contender, getting a big haul of picks, and truly re-tooling.

Pritchard is another question. His four-year, $30 million extension is an absolute steal for the Sixth Man of the Year. His upcoming $6.7M salary wouldn’t solve the tax problems by itself, but that low salary would certainly up his price in a potential deal.

Perhaps Boston thinks it can trim the fat on declining or less essential players and try to run it back in 2026-27. An alternative would be to trade White, Pritchard, and Hauser in addition to Holiday for short-term deals and let Porzingis stick around. That would clear a whopping $83.8 million, and open up nearly $60 million in cap room for the season when Tatum returns.

It would be a whole lot of uncertainty. That level of teardown could rip apart the fabric of Boston’s culture. Even if the internal promises to Tatum/Brown indicate this isn’t a true rebuild, it’s hard to trust someone on their word if the results are poor. There is the risk that if you break things apart you may be unable to build them again. But it could potentially raise the ceiling of the team once Tatum is back in the fold.

Which Way, Butler Man?

If you’ve taken anything away from this, know that Boston will be saying some tough goodbyes this offseason. And that general manager Brad Stevens will have many ways to accomplish this.

The fans’ goodwill after this injury effectively buys you a season to do what is needed. The title expectations are on hiatus. Stevens could trim salary, retain the core, and acquire some flexibility. Or he can take significant steps to reload Boston’s draft picks and try to fill as many rotation spots as possible with draft picks, enabling them to take a chance on acquiring more star talent.

There are so many variables at play here. Does the core want to stay? Will Al Horford wish to come back to a team that won’t be able to contend next season? Can stud head coach Joe Mazzulla coach a 45-win team the same way he can coach a 60-win team? Is Boston willing to risk getting Milwaukee’d by seeing one of their outgoing players end up on a team they’ll have to face in coming years, as Jrue Holiday did with their team? Most variable of all, does Boston believe that Tatum can come back strong after such a devastating injury?

I’d be surprised if any team is more active in trade calls this offseason. It’s an unusual position for a high-profile team to be quasi-sellers with two All-Stars on the roster, but thems the breaks. When that Shams Charania notification about Boston trading a piece away hits your phone this summer, you’ll know why these deals are being done.

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