The case for the Boston Celtics taking a “Gap Year”

The season is over and everyone processes that differently. If you aren’t ready to move on from the games just yet, feel free to bookmark this for later. For those of us who cope by looking to the future, let’s now turn our sad eyes towards the offseason.

A lot is already being said about the moves that the Celtics are most likely going to make this offseason. Ominous references to the 2nd apron, repeater tax, and roster restrictions are being thrown around as reasons why. I wanted to parse some of that out and make it clear why Brad Stevens has to consider making moves. Note: The reason is NOT that the new owner is “cheap.”

The Money Stuff

Let’s start with the numbers (courtesy of Spotrac). This season the Celtics were over the 2nd apron by $4.4M. They will be paying roughly $53.5M in taxes as a result (Insert the “not my money” line here). Next year the Celtics salaries are increasing quite a bit, largely due to Jayson Tatum’s new deal kicking in. As the salaries increase, the taxes increase exponentially. Right now, the Celtics are projected to be over next year’s 2nd apron by $20M. That would result in a whopping tax bill of over $238M!

Why does the tax bill go up so much? Mostly because the repeater tax kicks in. Brian Robb explains:

Boston has been a luxury tax team for three straight years now (including this year) so that brings painful repeater tax penalties into play beginning next year (repeater tax kicks in when you are in tax three of the last four years). If Boston elects to trim major payroll next year, they could dip under the tax ($187 million) and reset that clock for at least one year. Boston would need to be under the tax for two straight years for the repeater tax to no longer be a factor this decade. That would help with the team’s flexibility down the line and perhaps better reposition them to reload later this decade around a healthy Tatum.

So how much would they need to trim? Roughly $40M from next year’s salaries. Some candidates:

• Jrue Holiday $32.4M
• Kristaps Prozingis $30.7M (expiring after next year)
• Derrick White $28.1M (don’t you dare)
• Sam Hauser $10M

Note that it is hard to simply dump a salary and get no returning salary coming back. You would need to find a team with enough cap space to absorb the contract entirely. It isn’t impossible, but teams with that kind of space (like the Brooklyn Nets) will be looking for the best return they can get (perhaps getting a few first rounders for helping facilitate a Giannis trade, or maybe even trading for him themselves).

The alternative is to make unbalanced trades where you send out more money than you take back. An example would be to send Holiday to a contender for a mid-range salary and a younger player or draft pick. Bundle enough moves together and you can shed enough salary to make it make sense.

Bob DeChiara-Imagn Images

The Roster Restrictions Stuff

Here’s where I have to remind you of the current restrictions on the Celtics since they are over the 2nd apron. Here I get to quote myself:

As a 2nd apron team, the Celtics cannot send out two or more aggregated salaries together (so they can’t stack smaller salaries to bring back a more expensive player). They also can’t send out cash in a trade (some teams use this to incentivize the other team to take on more salary).

It gets worse too. Boston can only take back 100 percent or less of the salary that they send out in a deal. Typically non-tax paying teams have some wiggle room and can take back 125% (plus $250K) of outgoing salaries. The Celtics can’t go over by one cent.

The Draft Pick Stuff

As if all of that wasn’t bad enough, there’s stuff with the draft as well. When a team is over the apron for 2 years, their draft pick 7 years from now gets frozen (so still own it but you can’t trade it). And it gets worse: “If a team remains in the second apron for three out of five seasons, their frozen pick will move to the end of the first round, regardless of their draft performance.”

David Butler II-Imagn Images

So Now What?

I hope I’ve now painted a thorough picture of all the penalties and restrictions for a team trying to build and maintain a championship roster. My guess is that if the Celtics had won back-to-back titles, they might have been willing to accept those penalties (to an extent). However, even before the Tatum injury, there was building buzz pointing to the Celtics being willing to move off salaries to at least ease the tax burden.

Now, with the team unlikely to be considered a title contender next season, there’s little reason to expect them to pay all those taxes and absorb all those penalties. I know there is some hope of Tatum returning for the end of next season, but I’m not sure I want to see him rush back only to face the intensity and grind of the playoffs right away. So the safer bet would be to be cautious with his return.

We will spend a considerable amount of time on this blog discussing who should go and for what package we should hope to get in return. Some of the decisions can wait till the trade deadline as well. Thankfully I don’t think we’re in the position where we’ll have to attach draft assets to dump albatross contracts. Jrue is getting older, but I could see several contenders wanting to obtain his services. Porzingis frequently misses time, but he’s also extremely valuable when he’s on the court (and a low-risk expiring contract anyway). Hauser is a flamethrower and probably a bargain at $10M a year.

The Gap Year Stuff

All of the above was to make the point that we can’t just “run it back.” However, I’m not about to advocate for blowing everything up and going into “tanking” mode. The idea behind a “Gap Year” is to retain the nucleus (of Tatum, Brown, and White), dip under the apron, reset the clock on the repeater rules, and start building up the roster again.

This will be, perhaps, Brad Stevens’ greatest challenges as a GM. He will need to shed salary, while bringing back talent that is ready to contribute in 2026-27 and beyond (either directly in trades or through draft picks).

If he plays his cards right, there’s a scenario where they can add some promising players to their rotation that can be promising next year and ready to contribute when Tatum is ready to return.

Note: There’s a whole other discussion that could be had about the option of trading Jaylen Brown, but I’m saving that for another day.

I love this team. I will remember last year’s banner forever. The guys on this team have been a joy to watch and root for and I respect them immensely. It gives me no joy to move on from this era. Looking ahead, though, it is clear that change is coming.