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The Celtics Face a Critical Crossroads With Jaylen Brown

After turning in an All-NBA season, Boston’s second star has struggled mightily in the playoffs, particularly against the Heat. Will the Celtics still offer him the supermax this summer? Or could they consider shaking up their core?

Getty Images/Ringer illustration

In the aftermath of what can fairly be described as one of the most calamitous trouncings any NBA franchise has endured in, um, about a month, the loudest reverberation is also the most paradoxical.

The Boston Celtics won 57 games this regular season, their most in 14 years. Jaylen Brown was one of the most significant reasons. In what was far and away the most impressive stretch of his career, Brown made his second All-Star team and firmly established himself as an irrepressible shot-maker. Only eight players averaged more points than his 26.6 per game this season. Only seven made more total baskets.

The 26-year-old has never developed the playmaking tools that are ideally found in a primary option, and catch-all metrics aren’t a huge fan of his overall impact. But next to Jayson Tatum, embedded within a balanced roster full of ball handlers, enhanced by 3-point shooting and versatility, Brown’s ability to score is an essential part of Boston’s elite offense.

In these playoffs, though, despite a slight rise in minutes, his usage rate and scoring average have taken a noticeable dip. And then there’s what’s happening in the Eastern Conference finals. Down 0-3 to the Heat in one of the most shocking shellackings in recent memory, Brown is shooting a porous 37.7 percent from the floor, including 2-for-20 behind the 3-point line and not including an even more worrisome 2-for-4 from the charity stripe.

“I feel like we let our fan base, organization down, we let ourselves down and it was collective,” Brown said after a 12-point dud in Game 3. “We could point fingers, but in reality, it was just embarrassing.”

In 104 mostly flustered and sped-up minutes, where aggressive attempts to impose his will have resulted in the same mistakes that directly call back Boston’s collapse in the 2022 Finals, he has 10 assists and 11 turnovers. There was one stretch in the second quarter of Game 3 when he rushed a point-blank putback and then airballed a wide-open 3 one minute later. Maybe his hand is still bothering him, but that doesn’t explain all of these errors. (There’s also the myriad defensive issues that have plagued Brown the entire postseason.)

To make a bad situation more complicated, Brown’s train of alarming no-shows leads his team to a thorny, financially prohibitive predicament that will either destabilize their core and sabotage yearslong momentum or allow the Celtics to sustain one of the most impressive runs in the league.

One week before the conference finals started, Brown was officially named second-team All-NBA, a distinction that qualified him for a supermax contract that’s worth 35 percent of the team’s salary cap. That translates to $295 million over five years, starting in 2024-25. From Boston’s perspective, this reality is both a gift and a curse.

To explain the latter: Brown’s résumé and skill set aren’t a no-brainer for this type of deal. The cap is rising, yes, but it will also be under a new collective bargaining agreement that strips big spenders of some important team-building resources. Brown isn’t Nikola Jokic, Steph Curry, or Giannis Antetokounmpo, a franchise-carrying perennial MVP candidate who makes everyone around him better while regularly shredding scouting reports that have his name underlined in sharpie a dozen times.

But not being able to retain Brown at this stage in the organization’s life cycle would be a disaster. The Celtics may get washed out of the postseason, with Brown unable to exert his will against Miami’s string of overmatched individual defenders (he should annihilate any team that sticks Gabe Vincent on him), but they don’t have too many realistic options that are ultimately better than offering their second-best player whatever it takes to keep him around.

Even though the Celtics are 8-8 in these playoffs and outscored opponents with Brown on the bench during the regular season, they could not sniff a deep playoff run without him. Their two most probable recourses: Sign an exceptional, improving talent to a humongous extension and make changes elsewhere, or trade him for someone even better. (More on that later.)

It’s hard to see Brown—a proud vice president of the players union who’s already coming off a contract that wasn’t the max—accepting a penny less than the upper limit of what he can earn. And even as a roster that’s built to win right now, with aging vets like Malcolm Brogdon, Derrick White, Marcus Smart, and Al Horford all signed through at least 2025, the Celtics can’t afford to enter next season with Brown in the final year of his contract, able to hit free agency.

Meanwhile, Tatum, who just turned 25, can sign a $318 million extension next summer. Despite the Celtics’ current struggles against Miami—a club, by the way, that they eliminated last year on the road in a Game 7—Brown and Tatum’s compatibility is not the problem for a team that just finished first in net rating, second in offensive rating, and second in defensive rating. How many duos are better?

Jaylen Brown scored just 12 points in Game 3 at Miami.
Photo by Issac Baldizon/NBAE via Getty Images

Boston just made the Finals with this core, and Brown has played in 101 playoff games since he was drafted in 2016. If the Celtics extend this series, he’ll have appeared in more playoff games than anybody else in the NBA over that span. People who scoff at that fail to grasp how difficult perennial title contention can be in a league in which reigns are fleeting. Ask the Nets, Clippers, Sixers, Mavericks, Suns, Bucks, Grizzlies, Raptors, or Lakers about their climb to the summit, and how they responded after tasting success. Which team has fewer significant short- or long-term concerns than the Celtics right now? The Nuggets? Anyone else?

A Celtics optimist taking a 35,000-foot view of the situation could sum this series up as a miserable outlier, unworthy of a knee-jerk overreaction. According to various metrics from Second Spectrum, this is the worst shooting series of Brown’s career by a significant margin. His effective field goal percentage (39.3) is 9.9 percentage points below what an average player would convert on those same shots.

And on the other end, the Heat’s effective field goal percentage (60.5) is 9.6 percentage points higher than what was expected of them, based on who took the shots, from where they were launched, and a few other factors that try to gauge the quality of their looks. If that difference holds, it would be the highest any team has submitted in a series in Second Spectrum’s entire database. (Translation: The Celtics were shit out of luck.)

That doesn’t excuse Boston’s poor effort or rotational quagmires, or take anything away from Caleb Martin, Gabe Vincent, and Duncan Robinson’s incredible play. But the reality is, in a make-or-miss league, sometimes strategy is less relevant than people want to admit.

Normally, an opportunity to reward someone like Brown with a supermax would be cause for celebration. In Boston, it’s an elephant-sized pill to swallow, much less shortly after the Celtics’ still-beating heart was ripped from its chest by an arch rival.

Boston’s path forward is far from obvious, but it’s hard to see every key figure from this year’s unit back for another go-around. Joe Mazzulla is the likeliest scapegoat given how pretty much every other disappointed playoff team has responded to their own demise. Some alternative names are attractive: Monty Williams, Nick Nurse, Mike Budenholzer, and Frank Vogel have all coached in an NBA Finals, and three have won it all.

But the players aren’t blameless. And if ponying up the supermax for Brown isn’t something Celtics owner Wyc Grousbeck wants to do after watching the series unfold like an origami swan filled with skunk spray, the next steps could be an earthquake.

Short of Brown announcing his intention to explore free agency and break up with an organization that’s considered trading him in the past, a quick glance at the landscape, combined with Boston’s cap sheet, makes this scenario unlikely. Boston won’t deal Brown unless it gets a better player in the trade—not previously exchanging him for Kawhi Leonard, Jimmy Butler, or Kevin Durant when the Celtics seemingly had an opportunity to do so would sting just a bit. But the magnitude of Game 3’s shadow may elevate proposals that didn’t seem feasible on Saturday.

Brown’s expiring contract could scare off potential suitors that won’t surrender their most prized assets for someone who could walk in a year, but his age, versatility, and undeniable talent are extremely attractive. In a world where Boston decides to move on, sending him, Horford, and Payton Pritchard to the Clippers for Paul George and a first-round pick makes some sense for both sides. (Boston would be wise to ask about Leonard first.) A similar package to the Blazers for Damian Lillard seems less likely for a variety of reasons, but is something Boston should explore.

Would the Pelicans consider parting ways with Zion Williamson? Probably not. But if picks are involved … crazier things have happened. Could the Celtics extract someone like Darius Garland? Or Desmond Bane, attached to significant draft capital? Trae Young and Karl-Anthony Towns are obvious candidates, but it’s hard to see how either one moves Boston closer to a title than it currently is.

Some of these are fever dreams (for both sides), which is kind of the point. Boston is stuck between a rock and a hard place right now. That’s the power of a direction-changing loss. Brown has earned the supermax because he’s one of the 20 best basketball players in the world. The Celtics might not be jumping through hula hoops to offer him one of the largest contracts in professional sports. But it’s hard to see them being better off going another route. This series hurts badly, but patience should still be a virtue in Boston, where every ingredient to win it all is already there.