Let me start out by saying this argument isn’t a referendum on Jaylen Brown’s value as a player, at least in a vacuum. He’s a wonderful and deserving All-NBA talent, but that’s, unfortunately, only a piece of the picture. With the new collective bargaining agreement and its prohibitive second tax apron looming, the decision whether to pay Jaylen Brown a super max, which will begin around $50 million per year and end around $66 million, is much more complicated than “is he good enough to deserve it?” Again, without context, the answer is objectively yes. All-NBA second teamers are usually worth the super-max, but there’s the rub:

The damaging nature of the new CBA

Whether or not Jaylen is good enough to deserve the supermax isn’t the question. The real question is whether the Celtics giving the supermax to Jaylen is in the best interest of the franchise given the economic realities of the situation, which brings us back to the new CBA.

The new CBA has created a punitive second luxury tax apron that comes with massive penalties for teams that exceed it. The new line will be $17.5 million over the initial luxury tax line (the first apron is roughly $6 million or so over the tax line). The Celtics are $24 million over the current tax line, and that’s with Jaylen Brown on his below market deal (he has 1 year left). In other words, if the second apron existed today, the Celtics would be subject to these penalties.

With both Jays on a supermax, those two alone will occupy roughly 70% of the salary cap. The room gets eaten up very, very quickly after that. With several players locked up between $22 and $11 million,* Suffice to say, it is a foregone conclusion that the Celtics will exceed the second tax apron if they carry on their current trajectory.

Why is the second line so punitive? Here are the penalties for exceeding it, which primarily kick in for the first year of Jaylen’s supermax in the 2024-25 season:

• The Celtics can’t take back more salary than they send out in a trade (previously you could take back 125% of the salary you were sending out). This severely limits the ability to upgrade the roster via trade. You essentially have to find the perfect trade partner, or one that is below the second apron and willing to take on salary. Getting another team to take on salary usually costs assets.
• They will lose the taxpayer mid-level exception. This removes the only mechanism for the Celtics to sign a role player in free agency and they can only use minimum contracts to fill out the roster in free agency.
• They cannot sign buy-out guys looking to ring chase (so long as their previous contract is higher than the minimum, which it would be in basically every scenario).
• The Celtics would not be able to trade their first-round pick seven years out (would be the 2030 pick if this went into effect today). This seems like a minor hurdle, but this combined with the salary matching restrictions really reduces their flexibility in the trade market (especially since the 2026 pick is already subject to a swap).
• If the Celtics exceed the second apron in two of four years, their first-rounder seven years out is moved to the end of the first round, regardless of record. This creates the possibility where the Celtics spend now and pay for it dearly later if Tatum were to leave. It creates massive risk regarding an important future asset.
• There is one positive, the luxury tax bands will increase, which means they can spend more before they enter a higher level of the tax.

So, what does all of this add up to? Giving Jaylen the supermax will severely limit what the Celtics can put around the Jays. The $60 million luxury tax bill this season was already a record for the Celtics franchise. That bill will stand to increase to an exorbitant amount if the Celtics simply retain their current core without adding to it. Much more likely, the Celtics will be looking to shed significant salary in order to retain the Jays without more than doubling their current tax bill. That will mean losing key role players on the level of Derrick White, Grant Williams, and Malcolm Brogdon. And if the Celtics remain above that second apron even after they lose key guys? Well, then they don’t have any mechanism to replace them, even with lesser versions, because they are so limited in free agency and the trade market by the new CBA.

I know. It’s not my money — why do I care? I don’t in a vacuum, but the reality is that Celtics ownership simply will not pay double and triple their current tax bill. It’s not viable short-term and not sustainable long-term. If they decide to do so and are willing to pay record amounts of tax, then please throw this whole thing out and let’s pretend I didn’t write it, but I’m not banking on it.

It’s not about whether you think keeping Jaylen and this entire core intact makes sense. It almost certainly does. It’s about whether keeping Jaylen at the expense of the core makes sense. Is it worthwhile to try and compete with a roster that features two All-NBA wings, two or three good role players, and essentially nothing else? I would posit that it doesn’t.

As CelticsBlog’s own Keith Smith succinctly explained: “The new CBA is designed to break up teams like Boston and where they are headed salary-wise. It is what it is.”

Why trade him now, and what for?

The primary reasons for trading Jaylen now are two-fold: (1) he’s coming off his best season ever, so his value as a player is extremely high; and (2) trading Jaylen is in part a means to control the salary bill and trading him at his current salary number means you match salary at that value (roughly between $28 and $32 million depending on what league year he’s traded in). Waiting until he’s paid the supermax defeats a lot of the reason for trading him. Simply put, if trading Jaylen is in the cards, this offseason is the only time that it makes sense.

A quick aside: no other team can give Jaylen the supermax, and he cannot be traded for a year after he signs his supermax extension this offseason (another reason that the trade will come this offseason, if it does). When I discuss Jaylen trades below, it will be with the understanding that there is a wink-wink deal between Jaylen and the team he’s being traded to that he will get a normal max contract after the trade.

With that housekeeping out of the way, we are left with the ultimate question: what can you get that even makes trading Jaylen worth it? When evaluating Jaylen trades, here are the factors I’ll be weighing:

1. Because this is in part a cost savings exercise, I want the key player(s) in any deal to be locked up beyond next year at a reasonable number, or it’s extremely likely the player would re-sign at a number that makes keeping the complementary pieces on the roster possible.
2. I want them to provide things Jaylen doesn’t. It doesn’t make any sense to trade Jaylen for a worse version of himself. I’m looking for players that do at least one of two things on offense, preferably both: shoot 3s at an elite level (standstill and on the move) and/or elite level ballhandling/playmaking.
3. I’m also shooting for defensive upgrades, which should be doable since Jaylen’s defense comes and goes. In other words, I want the new players to be less redundant skill-set wise with Jayson Tatum.
4. I want good role players in addition to a player that fills 80-90% of Jaylen’s offense. Ideally, one of those role players is a center.

Without further ado, the trades.

Trade 1**: Tyus Jones, Luke Kennard, Xavier Tillman, and Desmond Bane for Jaylen Brown

Bane gives you elite shooting and is a better team defender while providing a significant portion of Jaylen’s offensive production. Jones and Tillman are very solid bench players that you can keep around for reasonable contracts (both only have one year left). Kennard is mostly cap filler, but he’s an ok bench wing and one of the best three-point shooters over the last few years.

The downside with this deal is that Bane only has one more year on his rookie deal. That’s ok though because the rookie max extension would be significantly less than Jaylen’s supermax (around $20 million by my rough estimate). Once Bane gets expensive, Kennard can be dumped for salary savings with very little pain.

Trade 2: Bogdan Bogdanovic and Dejounte Murray for Jaylen Brown and Payton Pritchard

Again, a downside here is that Dejounte Murray is not locked up, and if you can’t get an inkling as to what he thinks his value is, that could tank the entire trade. If he’s looking for something around the $30 million a year AAV range, then this makes some sense. That would give you Bogdan Bogdanovic and Murray locked up long-term around $50 million. It might cost you someone like Brogdon in a salary savings move down the line, but Bogie and Murray give you a lot more ballhandling, and both are steady hands that can generate decent shots late in games. Bogie is also an elite shooter from distance. Murray and Smart would be an insanely competitive defensive duo.

Trade 3: Mikal Bridges and Nic Claxton for Jaylen Brown and a 1st

Mikal Bridges would be the dream. There’s a world where he’s a more valuable player than Jaylen Brown next season. It very well may not happen, but he’s catching up offensively and he is quite easily one of the best defensive wings in the league. He’s a higher-level shooter than Jaylen, but obviously is not the shot creator in isolation that JB is (few are). He’s also locked up on an absurdly good contract, just in the mid-20 millions for the next 4 years. Claxton is an excellent big whose value I’m probably underrating with this trade (that’s why I threw the 1st in, but value-wise, I think you could argue for removing it). Regardless, he’s a poor man’s Rob Williams that can easily start when Rob misses games. He will need to be re-signed, but assuming that can get done for mid-teens, this trade accomplishes everything I’m looking for in a Brown deal.

So, there you have it. From an emotional standpoint, I would hate to see Jaylen go, and it’s a shame that as the Celtics begin to hit the Jays’ primes, this new destructive CBA comes into place. Just to be clear, I don’t want to trade Jaylen Brown. I’d like for him to stay and the Jays to win half a dozen championships together. Unfortunately, that doesn’t change the financial reality of the situation the Celtics are in. It should be a very easy decision to re-sign a player like Jaylen Brown long-term, but it’s not. Brad Stevens has some impossible decisions to make this offseason. I don’t envy him.