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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The youth are here to take over, yes. The old gods are dead and buried. There is no James, Curry, or Durant in this year’s final four. Even as their powers diminished, those four appeared in four of the last five conference finals. There’s not even a Jimmy Butler, who has made three of the last five.

Parity is another word looming large over this postseason. Since the Warriors dynasty broke apart, the 20 conference finals representatives have been comprised of 12 different teams. Much of the repetition comes out East, by far the weaker conference: the Celtics and Heat have 7 of the 10 ECF showings. Out West, the Nuggets, Mavericks, and Lakers have repeatedly appeared. Yet two conference finals in 5 years don’t scream dominance. More than ever, it feels like everyone has a shot.

That sentiment plays into an even more important theme in my eyes. When you look at the teams that have made deep runs, this year most of all, they took huge swings in acquiring talent. In this era of parity, those who push their chips in first are being rewarded. I want to explore the importance of forcing the window open and the rewards of temerity vs. the cost of timidness.

Dallas Swings, Thunder Go Down Looking

The Mavs-Thunder series is the clearest example of this idea. It’s frankly incredible how directly the trade ties between these two teams caused this series to shift.

Go back to the draft. Dallas owned a lottery choice but seemed intent on moving it to shed salary, and landed on sending Davis Bertans (and most importantly his $17M salary) with the 10th pick to Oklahoma City for the 12th pick. It’s hard to argue with the selections both teams made – OKC taking Cason Wallace while Dereck Lively II fell to Dallas – but the large trade exception Dallas created was huge. Sam Presti was handing an undeserved bailout to the Mavericks.

That exception was used to acquire Richaun Holmes, not exactly a game-changing acquisition, but it enabled them to do several things. After creating extra cap room, Dallas was able to acquire Grant Williams via sign-and-trade with Boston. Williams and Holmes did not pan out but became important salary ballast at the deadline. And this is where Oklahoma City only made things harder on themselves.

On February 8th, Dallas shipped out Holmes and Williams along with salary and picks for Daniel Gafford and P.J. Washington. Not only would these trades have been impossible without OKC’s draft night deal, but they helped even further by exchanging 2028 picks with Dallas to open up a 2024 first Dallas could use in these deals. It gave them the ammo needed to make two big deadline swings.

Meanwhile, Oklahoma City made calls but ultimately settled on a bunt single of a trade in acquiring Gordon Hayward at the deadline. Now fast forward to the conference semifinals to see the impact of those deals.

Gafford recorded 11/7.5/1.3 with 2 blocks per game across 6 matchups with OKC. P.J. Washington was murder for the Thunder, recording 18/8/2 averages while hitting a ridiculous 47% of his 8.2 threes per game. Fittingly, Washington’s free throws at the end of Game 6 closed out the series. Gordon Hayward managed 15 inconsequential minutes in the series. Sam Presti effectively sold the Mavericks a pair of knives only to watch his team be stabbed to death by said knives. One team swung, another watched, and the swinging team ended up moving on.

And they weren’t the only team undone by their own mistakes.

Minnesota Pays Up, Denver Counts Coins

If you follow the NBA on a deeper level, you’re probably aware of the Kroenke vibe. They’re willing to cut checks for big players when necessary but will always find a way to cut costs in the end. This loss to Minnesota felt like a culmination of the pitfalls that philosophy comes with.

Minnesota threw a contract at GM Tim Connelly that Denver did not want to match, and it seemed prudent after last season as GM Calvin Booth helmed a championship team. Yet it was clear to all that it was Connelly who had his prints all over the squad. The entire starting lineup, one that dominated the 2023 playoffs, was drafted or acquired by Connelly before his departure. The Timberwolves saw what he could do and put unequivocal faith in him to build a team that could dismantle his creation.

The Rudy Gobert trade was unfairly maligned at the time and took only a year to prove everyone wrong as he anchored the best defense in the league. While Minnesota took more swings to improve on this Gobert team (acquiring Mike Conley, signing Nickeil Alexander-Walker, and extending their stars) Denver was content with what they had after the title. Calvin Booth told Bruce Brown not to let the door hit him on the way out. They acquired more picks to try and hit through the draft instead of getting proven talent to augment a championship roster.

When these two teams faced off, it was clear what kind of impact these moves made. Minnesota had more depth, more athleticism, and a feeling of confidence that Denver could not match. The stars performed, yes, but the role guys made the difference in the series. NAW’s defense and shooting confidence played a role. Mike Conley hit timely shot after timely shot. And on Denver’s side, guys like Christian Braun and Peyton Watson could not affect the series when the stars sat. If only there was a playmaking and defending wing Denver had in their grasp.

The throughlines of this between the two squads aren’t quite as clear as Dallas and OKC, but you can see how aggression from Minnesota’s front office won over Denver’s complacency. That’s why Minnesota is fighting for its deepest run in franchise history while Denver hits the racing track.

Knicks, Pacers Going Out On Their Shields

Regardless of who won that series, nobody could argue the Pacers or Knicks were withholding chips. Both teams went pedal to the metal during this season and reaped the rewards.

Indiana took perhaps the biggest swing of the entire deadline in acquiring Pascal Siakam, and he responded by powering them through the first two rounds of the playoffs as their leading scorer. Much hand-wringing was done when the deal was made, yet nobody can argue with the results as Indiana reaches their first conference finals in a decade.

The Knicks took an even larger amount of swings. They made moves for OG Anunoby, Bojan Bogdanovic, Alec Burks, Precious Achiuwa, and Donte DiVincenzo over this past year. Donte and OG were among the primary reasons why the Knicks could win a street fight-type series against the Sixers despite the absence of Julius Randle. Had they not completely fallen apart with injuries (I am looking at you with malice, Tom Thibodeau) it feels like they would be playing Boston right now.

Sure, you could argue trading Obi Toppin to the Pacers this offseason burned them. But Toppin was buried on the depth chart at the time and would have likely fallen further behind after that bevy of acquisitions. And a 10 PPG role player who is generally heinous on defense isn’t going to be the one who got away.

Both teams swung, and both teams reaped huge rewards. And it gave them a puncher’s chance against the beasts of the East, another team not shy to make moves.

Boston Doesn’t Back Down

As previously mentioned discussing the parity of the league, only the Heat could match Boston in conference finals appearances over the previous four seasons. Yet those three showings had resulted in zero titles. In this era of “what have you done for me lately?”, many questions were being asked. Is Jayson Tatum the kind of guy who can lead a title winner? Can Jaylen Brown be his #2? At what point do we shake this up?

Instead of caving to those notions, Brad Stevens doubled and tripled down. He boldly chose to trade Marcus Smart for a better-fitting star in Kristaps Porzingis, needing little draft capital to do so. Then he went even further by taking advantage of the Damian Lillard trade to add Jrue Holiday. Instead of breaking this team apart, he only fortified their chances and was rewarded with a 64-win team that is stampeding through the Eastern Conference.

Even with Porzingis injured and unlikely to return until late in the conference finals, Boston holds a 3-0 series lead over the upstart Pacers and are overwhelming favorites to come out of the East, perhaps fully healthy. Jrue has been the playoff chess piece they needed, taking on important defensive matchups while canning 43% of his 4.7 threes per game. The role players don’t need to hit as hard when you boast Jayson, Jaylen, Jrue, Derrick White, Porzingis, and Al Horford. No team in this league can even hold a candle to that top 6.

Boston chose to push in every chip they could and are being thoroughly rewarded.

What Does This Tell Us?

Yes, young stars are indeed playing a major role. One of these four teams will represent a new title winner. All four are led by a star who is 26 years old or younger.

That only enhances the point here. All four teams could have sat back and gone “Well their primes haven’t even started yet, so we can wait” and chose instead to make short-term moves. The 2024 championship winner will be a team led by young stars whose management chose to force the window open instead of waiting for it to open naturally. The teams that have gone home already by and large chose to sit on their hands and wait.

Contention windows don’t stay open as long as you expect. Sometimes they don’t open at all. If you have the stars capable of delivering a deep run toward the Larry O’Brien trophy, take the swings now before your chance passes. It may pass sooner than you think.

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