It’s time for the Boston Celtics to pay Jaylen Brown what he’s worth

Got an anecdote for you, Boston Celtics fans. There’s a great episode of The West Wing about ten-word answers. President Jed Bartlet is about to enter the ring for the first debate of his re-election campaign, and his staff have spent the week agonizing about how to answer the questions of the nation in a mere ten words.

The President’s lead attack dog Josh Lyman is sweating the event, worried that the tepid, unsure version of Bartlet—nicknamed Uncle Fluffy—will emerge instead of the sharp and ruthless political master that the moment requires.

Republican nominee Rob Ritchie crushes the opening fastball from the moderator, nailing a ten-word answer that Bartlet’s camp had been searching for. But Jed finds another gear, and asks for the next ten words, demanding we inject some complexity into a political climate bogged down in its search for simplicity. It’s a killer line. Josh lets out a mean fist-pump, emphatically screaming “Game On!” in the war room, and Bartlet dominates the debate, effectively putting the election in the win column.

But I’m not Aaron Sorkin. I write about the Boston Celtics, and believe it or not, this is all actually about Jaylen Brown. And I have a ten-word question with a one-word answer:

Should the Boston Celtics pay Jaylen Brown almost $300 million?

Yes.

Brown is a lot like Bartlet—yes, I’m aware this West Wing metaphor has probably overstayed its welcome—in that his supporters constantly worry which version of him will show up. There’s superstar Jaylen Brown, who is liable to score every single time he touches the ball, play physical and unyielding defense, and bring relentless energy to every corner of the court.

But then there’s Uncle Fluffy, who turns the ball over like it’s his job, can’t play defense whatsoever, and looks afraid to shoot or put the ball on the floor because he knows he’s going to get stripped.

In a normal place during normal business hours, none of this would be making headlines. Except this is Boston, and the Celtics not having won a championship in 15 years is starting to feel like a long time. And Dr. Jaylen and Mr. Brown is up for a colossal extension, so all of this is suddenly peak intrigue.

If you just want the gist: pay the man. Superstars are impossible to find in this league, and while it’s possible to overpay for them, it’s really, reeeeeally hard to. If you don’t pay him, you have to trade him. That’s a bad idea barring extraordinary circumstances. There, you got the gist.

The full lowdown is a bit more touchy, but that’s what we do here at Oliver Fox Overcomplications Incorporated. There’s a fourfold conversation to be had, so let’s have it: economics, basketball, Brown’s relationship to the city, and his trade value.

Let’s go.

To me, the ins and outs of the Sporstcanomics involved with this extension are basically a non-factor. His deal, alongside whatever super-ultra-mega-deal that Tatum is going to get next year, will place the Boston Celtics squarely past the horrifying “second-apron” of the luxury tax sometime in the next few years, which will drastically restrict flexibility with roster building.

But I don’t really care, because you simply do not have a chance to win a title in the NBA without two or more bona fide stars. Tatum and Brown have proven for four consecutive seasons that a core built around them gives the C’s a real chance at a championship, and a chance is all you are ever going to get. Nothing will ever be guaranteed, no matter how hard you try… *cough cough Brooklyn Nets*

Beyond financial fearmongering, the main reason to not pay (and thus to trade) Brown is his infuriating tendency to become Uncle Fluffy on the basketball court when the Boston Celtics need him the most.

Brown’s weaknesses—particularly his turnover happiness—have gotten a lot of play in Celtics circles since they tend to appear in really big games. For two straight Eastern Conference Finals-es, the Miami Heat have made a living out of diving at the ball every time Jaylen puts it on the floor, which totally sucks.

Other times, he’ll simply dribble it off his foot or just lose the handle entirely, something I resonate with because I do that stuff when playing against my friends on the concrete blacktop at my local elementary school, which is probably a bad sign.

Of course, everyone has a weakness, even the new everyone-thinks-he’s-the-best-player-in-the-world belt holder Nikola Jokić, whose defensive foot speed can make guarding quicker bigs quite the challenge. Brown’s issue is that his turnover problem is so blatantly obvious even to viewers at home that it can seem worse than it maybe actually is.

When Jokić misses a step against Bam Adebayo, nobody notices. But when Brown loses the ball after dribbling into three guys with 17 seconds left on the shot clock, he is giving up an entire possession for what feels like no reason, driving everyone completely insane.

Lost in all this sauce is the fact that Brown had the best season of his career, and it’s not particularly close. He made the All-NBA Second Team, and I personally counted three times this year when I legitimately questioned if he was better than Jayson Tatum.

Other than his first year in the league, when he took a measly five shots per game and Tatum was still at Duke, every season has found me probably-almost-certainly-but-not-quite-absolutely-certainly-sure that Tatum was better than Brown, but there are always moments where he is the best guy on the court. There will be next year, and there will be the year after that.

But there’s no doubt that Tatum is the golden child of the Boston Celtics, which adds another wrinkle to Brown’s future: his sometimes adversarial relationship with the city and fan base.

Brown has had his share of off-court drama, complete with anti-Semitic allusions, a questionable professional relationship with Ye and Donda Sports, and an infuriating refusal to get the COVID-19 vaccine. All the while, Boston isn’t the easiest place to play and a heavy history of racism and unforgiving fans is not lost on the still astute Brown, who mentioned that difficulty in a pair of profiles for the New York Times and The Ringer.

Moreover, are the unending trade rumors, real or media-concocted? Brown’s name tends to turn up in trade speculation whenever a star—Anthony Davis, Kevin Durant, Damian Lillard, to name a few—decides they want out of their current situation. Tatum’s name is generally nowhere to be found, which makes sense but also probably stings for Brown, who, for all his faults, has worked his tail off for the Celtics year in and year out.

But that’s the business. When you aren’t winning a championship, people are asking questions. The best player is typically off-limits, so Brown is the next closest question mark.

This leads to part four of the fourfold Jaylen Brown evaluation extravaganza: trade value.

What the Boston Celtics can get back for Jaylen Brown in a trade is unclear

The reason I’m against this whole concept is a question of return. Sure, shipping off Brown to wherever seems fine until you start to ask who you are getting back. Save for Julius Randle, who I assure you the Boston Celtics do not want, the rest of the All-NBA teams are probably off the table, so what else you got?

A bunch of first rounds picks from a team even more desperate than the Celtics? That’s not going to work for me since the Cs are in win-now-or-win-kinda-soon mode and not a full rebuild.

Hey, Portland looks like a fire sale waiting to happen, so how about the third overall pick and Anfernee Simons? Sounds great, except it doesn’t. Simons would be a defenseless guard on a team with way too many guards, and the third pick is probably Scoot Henderson who—get this—is also a small guard.

Oh, what about Damian Lilla…no. Shut up. I am canning this whole Damian Lillard fiasco right this second. It is a disgrace to the rule of logic in the universe, and a total non-starter if you want to talk turkey with me at any upcoming Celtics Trade Speculation functions. Trading an All-NBA, 26-year-old wing for an aging small guard due to earn $63 MILLION in 2026 at the ripe old age of 36 who cannot and will not play defense makes about as much sense as letting a polar bear into your living room and offering him dinner and a light salad. If I see one more Twitter edit of Lillard in a Boston Celtics jersey, I might just lose my mind.

As I said before, barring extraordinary circumstances, trading Brown is a bad idea. But if Brad Stevens wakes up tomorrow, looks in the mirror, talks to ownership and Head Coach Joe Mazzulla, looks in the mirror again, and decides that paying Brown almost $300 million just simply cannot be done, trading him is the only way to go.

So let’s talk about extraordinary circumstances.

Every summer, and I mean every summer, someone big decides that they want out. Sometimes it’s relatively chill, like Donovan Mitchell, who is a great player but not a world-beater by any regard. But sometimes it’s Kevin Durant, who is a possibility to be the best player in the world whenever he wants to be.

That probably struck a chord, because Brown was thrown into the Durant conversation pretty hard last year, and I’ll be the first to say it: I talked myself into a JB-for-KD trade. Durant is better than Brown at basically everything, and the four years left on his deal made a Tatum-Durant core look like a four-year reign of terror that would rival Robespierre’s actual reign of terror. It was not to be, which is perfectly alright. But I was ready for it.

Durant-level players are the extraordinary circumstances I have been alluding to. The only scenario where I think parting with Brown makes any sense is if a cosmos-altering player suddenly demands to be traded. I’m talking a demand, not a want, not a polite request, but an unequivocal statement that they will never ever suit up for their current team ever again. And I’m also talking Luka Dončić or Giannis Antetokounmpo-level dudes. This is so unlikely to happen that I was hesitant to even include it as a possibility.

But being the only scenario I am willing to entertain, I had to give it a few seconds. It would take a witches’ brew of insanity, but it’s technically possible.

The ultimate UNO-reverse-card moment would be if Brown himself is the guy who wants out. That wouldn’t have shocked me before 7:00 pm Eastern time on May 10th, 2023, but as soon as NBA Communications tweeted that Brown had made All-NBA, his asking for a trade became leagues less likely.

That’s because the Boston Celtics can offer Brown about $100 million more than any other team can since he is a homegrown player. Call me crazy, but voluntarily turning down that much money seems like it would take more willpower than exists on planet Earth, so if Brown actually doesn’t want the contract…well, uh…good for him.

In any case, Brown is worth more to the Celtics than whatever he may be worth as an asset, and while I understand the sticker shock of his contract, that is just what superstars are going to cost going forward. All signs point to a ballpoint pen on a very expensive sheet of paper, so it’s time to pony up and pay the man.

And honestly, I just think that the “Can Jayson Tatum and Jaylen Brown win a championship together?” ship has sailed, hit an iceberg, and sunk to the bottom of the ocean. To me, that ten-word question has the same one-word answer as the last one: yes.

That doesn’t mean they will, nor does it mean that they will never play for different teams. But I know that a nucleus of those two can make it happen, and I desperately, urgently want it to. And I know deeeeeep down that even the biggest Brown trade-hawks do too.