Let me start by saying that this argument is not a referendum on Jaylen Brown’s worth as a player, at least in a vacuum. He’s great and deserves an all-NBA talent, but that, unfortunately, is only part of the picture. With a new collective bargaining agreement looming and its second tax-blocking apron, the decision to pay Jaylen Brown a supermax sum, which would start at about $50 million a year and end at about $66 million, is a lot more complicated than “Is it good enough she’s worth?” Again, without context, the answer is objectively yes. Normally every NBA second-team player is worth the cap, but there’s the rub:
The disruptive nature of the new capacity building coalition
Whether or not Jaylen is good enough to deserve a supermax remains to be seen. The real question is whether giving Jaylen the Celtics supermax 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 created a deluxe, punishing second tax arena that comes with massive penalties for teams that pass it. The new line would be $17.5 million over the initial luxury tax line (the first apron is about $6 million or so over the tax threshold). The Celtics are worth $24 million above their current tax line, and that’s with Jaylen Brown in his deal below the market (he has one year left). In other words, if the second apron is in place today, the Celtics will be subject to these penalties.
With both Jays at the supermax, those two alone would take up nearly 70% of the salary cap. The room is taken up very quickly after that. With several players locked up between $22 and $11 million, suffice it to say, it’s inevitable that the Celtics will get past the second tax apron if they continue on their current trajectory.
Why is the second line so punitive? Here are the penalties for overstepping it, primarily starting with Jaylen’s first year Supermax in the 2024-25 season:
- The Celtics can’t recover more paychecks than they send in the trade (Previously, you could get 125% of the salary you were sending back.) This severely limits the ability to upgrade existing ones via trade. You basically have to find the perfect business partner, or a second apron less partner and willing to take the paycheck. Getting another team to take over the salary usually costs assets.
- They will lose the mid-level exemption for taxpayers. 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 can’t sign buy players looking to chase rings (As long as their previous contract is above the minimum, which they would be in basically every scenario).
- The Celtics would not be able to trade their first-round pick after seven years (It would be the 2030 pick if this went into effect today.) This seems like a minor hurdle, but that and the salary-matching constraints really reduce their flexibility in the commercial marketplace (especially since picking 2026 is already subject to a trade-off).
- If the Celtics pass the bib for the second time in two out of four years, Their first round after seven years was moved to the end of the first round, regardless of the record. This creates a possibility where the Celtics spend now and pay dearly for it later if Tatum were to leave. It creates enormous risk with respect to 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 tax.
So, what does all this add up to? Giving Jaylen the supermax would severely limit what the Celtics could put around the Jays. The $60 million luxury tax bill this season was a record for the Celtics. That bill would grow to an outrageous amount if the Celtics simply kept their current core without adding to it. Most likely, the Celtics will be looking to shell out a big paycheck in order to keep the Jays without doubling their current tax bill. That meant losing key players at the level of Derrick White, Grant Williams and Malcolm Brogdon. And what if the Celtics stayed atop that second bib even after they lost key players? Well, then they don’t have any mechanism to replace them, even with lower releases, because they are very limited in the free agency and commercial market by the new CBA.
I know. It’s Not My Money – Why Do I Care? I’m not in a vacuum, but the fact is that Celtics ownership isn’t going to pay twice and triple its current tax bill. It is not viable in the short term and not sustainable in the long term. If they decide to do this and are willing to pay standard amounts of tax, then please get this whole thing out of the way and let’s pretend I didn’t write it, but I don’t deal with it.
It’s not about whether you think keeping Jaylen and this whole core makes sense. Almost certainly. It’s about whether keeping Jaylen at the expense of the core makes sense. Is it worth trying to compete with a roster that includes two NBA wingers, two or three good players, and basically nothing else? I would assume it is not.
As CelticsBlog’s Keith Smith put it succinctly: “The new CBA is designed to separate teams like Boston from where they lead in terms of salaries. It is what it is.”
Why are you trading it now and why?
The main reasons Jaylen is now traded are twofold: (1) he’s coming off his best season ever, so his value as a player is very high; and (2) trading Jaylen is partly a way to control the salary bill and trading him at his current salary number means you match salary at that value (between roughly $28 million and $32 million depending on the year of the league he trades). Waiting until the supermax pays off defeats a lot of the reason for trading it. Simply put, if trading Jaylen is in the cards, this off-season is the only time it makes sense.
A quick aside: No other team can give Jaylen a supermax, and he can’t be traded for a year after he signs his supermax extension this offseason (another reason the deal is going out this season, if it ever does). When I discuss Jaylen’s trades below, it will be understood that there is a wink deal between Jaylen and the team he’s being traded to that he will receive the maximum regular contract after the deal.
With that housekeeping out of the way, we’re left with the ultimate question: What can you get to make Jaylen’s trading worth it? When evaluating Jaylen’s trades, here are the factors I would weigh:
- Partly because this is a cost-saving exercise, I want the key player(s) in any deal after next year to be locked out at a reasonable number, or very likely to re-sign a player at a number that makes keeping the supplementary pieces on the roster possible.
- I want them to offer things that Jaylen doesn’t. It doesn’t make sense to trade Jaylen in for a worse version of himself. I’m looking for players who do at least one of two things when attacking, preferably both: shooting 3s at elite level (stopped on the move) and/or ball handling/playmaking at elite level.
- I’m also shooting for defensive upgrades, which should be doable because Jaylen’s defense comes and goes. In other words, I want new players to be a little less skill-wise with Jason Tatum.
- I want two good players as well as one who will fill 80-90% of Gelene’s attack. Ideally, one of these players is the center.
Without further ado, trades.
Trade 1**: Tyus Jones, Luke Kennard, Xavier Tillman and Desmond Bane for Jaylen Brown
Bane gives you superior shooting and is the team’s better defender while providing a large portion of Jaylen’s offensive production. Jones and Tillman are two very strong players off the bench that you could keep around for reasonable contracts (they both only have a year left). Kennard is mostly a cover filler, but he’s a good bench winger and one of the better three-point shooters over the past few years.
The downside to this deal is that Bane only has one year left on his rookie deal. That’s okay because the rookie’s max reach will be much less than Jaylen’s supermax (about $20 million by my rough estimate). Once Bane gets too expensive, Kennard can be dumped to save the paycheck with little pain.
Deal 2: Bogdan Bogdanovic and Degonte Murray for Jaylen Brown and Payton Pritchard
Again, the downside here is that Dejounte Murray is not a closed door, and if you can’t get an idea of what he thinks his value is, it can disrupt the entire trade. If he’s looking for something close to $30 million in AAV range a year, that makes sense. That would give Bogdan Bogdanovic and Murray in the long run about $50 million. Someone like Brogdon might cost you salary savings down the line, but Bogie and Murray give you plenty of maneuverability, and they’re both steady hands that can generate decent shots late in games. Bogie is also a long range shooter. Murray and Smart would be an insanely competitive defensive duo.
Trade 3: Michal Bridges and Nick Claxton for Jaylen Brown and Ol
Michal Bridges would be the dream come true. There is a world where he is a more valuable player than Jaylen Brown next season. It may not go very well, but he is catching up offensively and is one of the better defensive wingers in the league. He’s a higher level shooter than Jaylen, but clearly not a shot-maker apart from JB (few of them). He’s also held on a ridiculously good contract, only in the mid 20 million for the next four years. Claxton is an excellent big company I’m probably underestimating with this trade (that’s why I threw in the first, but in terms of value I guess you could argue to remove it). Regardless, he’s poor guy Rob Williams who can easily start when Rob misses games. He’ll need to be re-signed, but assuming that can be accomplished for his mid-teens, this trade fulfills everything I’m looking for in a Browns deal.
So, there you go. From an emotional standpoint, I’d hate to see Jaylen go, and it’s unfortunate that as the Celtics start to get into the Jays’ starting blocks, this devastating new CBA comes in its place. Just to be clear, I don’t want to trade Jaylen Brown. I want him to stay and the Jays to win six 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 for the long term, but it isn’t. Brad Stephens has some impossible decisions to make this off-season. I don’t envy him.
*All ceiling numbers and salaries from Spottrack.com
** All trade photos from fanspo.com