There are two assumptions we need to agree upon before really getting into this: 1) Jaylen Brown is going to be paid a lot of money on his next NBA contract 2) to be worth that money, he’ll need to actualize some of his supposed “upside.”

I hate the term “upside.” It’s purposefully vague. The implication is “upside” to achieve something, which can mean different things for different players. In the conventional sense, I believe Memphis Grizzlies big Jaren Jackson Jr. has considerable “upside,” but it’s not upside to be an offensive initiator, obviously. Instead, it’s upside to leverage his instincts, size, and movement skills into generational defensive impact, upside to capitalize on his shooting—with versatility off the dribble and off movement—to put traditional big men in uncomfortable positions defending the perimeter, upside to expose defenders attacking closeouts and in faceup situations using his advanced handle.

It’s with specificity that the term “upside” gains value.

Hopefully, the first point won’t be contentious at all. Good young players get paid. Good young wings get paid a lot. From Andrew Wiggins to Harrison Barnes to Otto Porter, whether it’s an extension or contract with a new team or contract with an incumbent team, they all get paid. For the purposes of the second assumption, the actual number doesn’t matter all that much. Brown’s going to be paid enough—somewhere between $100 million over four years and $170 million over five, if I had to hazard a guess—that he’ll need to be a centerpiece, a star going forward.

So, let’s get specific on what “upside” means for Jaylen Brown. Again, I don’t think it’ll be contentious to say some of that “upside” should come from Brown’s defensive acumen, where he’s a versatile and strong guard/wing defender. However, as is true for nearly every non-big in the NBA, offense will be far more deterministic of Brown’s star equity.

The case for Brown’s offensive stardom undoubtedly stems from scoring, which is where the whole thing starts to unravel. First, there’s the assumption that Brown can scale up his usage and score at a higher volume. More importantly, there’s the neglect of what scaling up usage means in terms of role on a basketball court, and that’s where I really become dubious of Brown ever living up to his next deal.

In 2018-19, the lion’s share—61.8% of his possessions—of Brown’s offense came from spot ups and transition. On pure volume of possessions, he ranked 9th in the NBA in spot up attempts and 19th in transition. Scaling up what Brown already does isn’t really a viable option, because a team can only generate so many spot up and transition looks for a given player. For Brown, a larger role will mean a different role.

One conceivable approach could be diversifying Brown’s off-ball game, deploying him like Klay Thompson or Paul George prior to the 2018-19 season. He’d sprint off screens, taking more difficult attempts, but still assisted looks in which he wouldn’t have to create with the ball in his hands. The issue there is there’s absolutely no evidence Brown can be a movement shooter like the players who have succeeded in that role. In 2018-19, he finished in the 27th percentile on just 31 off-screen shot attempts.

Far more probable would be conventional star usage: ball in his hands, heavy doses of pick-and-rolls, isolations, and hand offs. And if you just look at Brown’s individual scoring numbers in those play types, you might find some signs for mild optimism in something like 75th percentile efficiency on (a low volume of) isolations in 2018-19. However, I’d advise extreme skepticism when considering Brown’s upside for self-creation:

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Among Brown’s biggest hurdles as a self-creator is his handle. He’s pretty mechanical and seriously lacking the shake department, rendering his attempts at deception largely useless. His arsenal is devoid of advanced dribble moves beyond something like a simple in-and-out, and he has neither the control nor creativity to string together a series of moves.

A lack of off-hand refinement seriously limits Brown as a handler, too, as you can see Jonathan Williams doesn’t buy that Brown is actually going to his left, eliminating the threat the in-and-out poses in the first place. Williams can also sit on Brown’s right with impunity, knowing he isn’t going anywhere else. Defenders zeroing in on Brown’s right is a consistent strategy:

Again, Brown goes to the in-and-out. Again, its deceptiveness is completely squandered by a player who doesn’t really threaten to go left. In this case, though, Brown is so predictable that Eric Bledsoe is able to beat him to the spot on his right and draw the charge in a semi-transition situation that should heavily favor the offense. Lack of left hampers Brown’s finishing as well:

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Brown gains a step on Joe Harris. He could go up on the left side of the rim for a normal lefty finish. After he goes up and under, he could use his body as a shield and spin the ball home with his inside hand. Instead, he brings the ball to his right and to Jarrett Allen, setting up an incredibly easy blocked shot.

Prodigious athleticism might incline one to think Brown’s statistical profile as a slasher would be impressive, but the stats pick up on his limitations as a self-creator. In 2018-19, 63% of Brown’s makes at the rim were assisted, which ranked in the 50th percentile among wings, per Cleaning The Glass. He’s not overwhelming with burst and bounce, but relying on creators to put him in advantage situations to get to the rim.

Troubling as well are Brown’s finishing woes. If you limit the sample to rim attempts in the half court (which I would have done for the assisted numbers too if that data were available) to get a more accurate picture of finishing ability outside of those uncontested transition run outs, it isn’t pretty. Among 54 forwards who attempted at least 150 half court shots at the rim in 2018-19, Brown’s points per possession ranked 41st. It’s a nasty combination of bad touch, an inability to create separation, and an undeveloped off hand.

More importantly, this is where you have to consider what on-ball usage actually means in the context of a basketball game rather than a Synergy chart. It means making decisions, and that’s a department where Brown struggles immeasurably:

Brown blows by Paul Millsap on the closeout, which triggers help from Mason Plumlee. This is all easy to process for Jaylen: someone else’s man is now in front of me, therefore that player is open, so I’ll shovel it over to him.

What he needs to do is see the next step. As Plumlee breaks for the rim, Monte Morris takes off for Al Horford, preventing the mid-range marksman from draining an uncontested look. Horford then moves the ball to Morris’ primary assignment, Terry Rozier. By the time, the ball finds its way to Rozier, though, the defense is able to rotate and recover, and just like that, the advantage Brown created by blowing by Millsap is gone.

Brown needs to skip steps here. He must understand that Plumlee’s rotation won’t be the only one, that there’s a domino effect. Heck, he just needs to see Morris break for Horford and understand what that action means. If Brown rises up and hits Rozier with the skip pass here, Denver has two defenders committed to Brown, one to Horford, and two for Boston’s other three players. Rozier either shoots an open 3 or Torrey Craig decides to close out to Rozier, leaving Tatum open for 3. Either way, it’s a far better outcome than the eventual Rozier turnover.

Contrast Brown’s simplistic read with a more complex one from his teammate, one of the league’s more advanced decision-makers on the wing:

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Gordon Hayward doesn’t really gain a step on Brook Lopez, but Milwaukee’s aggressive no-rim policy means he draws help anyway. Pat Connaughton slides down off Jaylen to prevent Hayward from getting to the rim, leaving Brown open. Hayward sees the next step. Giannis, behind Connaughton’s help on the ball, inches over to zone up the weak side, responsible for both Brown and Tatum. But the Brown cut forces Giannis to commit more to him than Tatum. Hayward sees all of this behind the initial reaction to his drive and makes the proper skip pass to Tatum, whose hesitance to launch the 3 bites the Celtics. These are the advanced reads star wing creators make.

Unfortunately, advanced reads are the least of Brown’s problems:

This is another opportunity to capitalize on Milwaukee’s aversion to rim attempts, and it’s super simple. Jaylen blows by Giannis on the closeout, Bledsoe slides over from Tatum on the strong side corner one pass away. Jaylen should see Bledsoe obstruct his path, understand Tatum is open, and flip it to his teammate for the uncontested triple.

Alternatively, as George Hill sinks off Kyrie Irving a bit, Brown could laser it to the wing for an uncontested look there. Instead, he goes directly at Bledsoe, and it’s not until he’s completely out of options that he evaluates his surroundings and kicks to Kyrie, having waited too long to profit from the advantage he initially gained on the Giannis closeout.

Take a read that’s easier still:

This is just a standard pick-and-roll, the staple of every modern NBA team’s offense and a sequence of actions every player should understand fully. As Zach LaVine goes over the screen and Cristiano Felicio meets him on the other side, Irving delivers the pocket pass to a rolling Daniel Theis. Lauri Markkanen does his job, sliding over from the weak side corner to meet Theis, and Wayne Selden does his by coming off Brown to zone up the weak side and defend both Brown and Hayward.

With Selden shutting down the passing lane to Hayward, Theis makes the proper decision, sending the ball Brown’s way. Selden recovers to Brown, but he has two good options: 1) he has enough space to shoot 2) quickly move the ball to Hayward, who will have an open catch-and-shoot look as Markannen recovers. Shooting an open catch-and-shoot 3 and moving the ball one pass away while stationary are exceedingly easy decisions to make. Naturally, Brown does neither.

The disaster that is this possession is magnified by the decisions Brown proceeds to make. As he drives to the hoop, he draws help from Felicio. Behind that initial help is Ryan Arcidiacono moving over from the weak side corner to check a diving Theis. Brown should see this and hit Rozier in the corner with the skip pass, but opts for a comically bad runner instead.

Brown’s decision-making woes present themselves rather strikingly in his statistical profile. Among wings in 2018-19, his assist percentage ranked in the 28th percentile, ratio of assist rate to usage rate in the 5th percentile, and turnover percentage in the 43rd percentile. It’s not just a matter of role. In the opportunities he has, Brown’s ability to make decisions is horrendous.

Historically, even in limited roles, players who have evolved into star wings have demonstrated an elite aptitude for decision-making. Paul George, in his third season, ranked in the 90th percentile in assist percentage and 78th in assist to usage ratio. Jimmy Butler, in year three found himself ranking in the 58th and 63rd percentiles in those stats, while seriously limiting turnovers, placing in the 64th percentile in turnover percentage. Kawhi Leonard, a very limited playmaker for a wing of his caliber, owned third-year percentiles of 70th, 65th, and 63rd in assist percentage, assist to usage ratio, and turnover percentage. Brown’s teammate, Jayson Tatum, in just his second year, found himself in the 66th, 37th, and 62nd percentiles in those three stats.

Growth into a player capable of shouldering a heavy on-ball role doesn’t just happen for players who haven’t demonstrated those intellectual chops early in their careers. Basketball intelligence is not an obvious, easily-perceived limitation, but it’s the biggest one there is.

I understand the somewhat nebulous terms “feel” and “IQ” can be hard to grasp as concrete limiting factors, so let’s contrast them with a far more overt limiting factor of a recently-extended young player from Brown’s 2016 draft class.

It’s very easy to see why a complete inability—or rather, unwillingness—to shoot jump shots hampers Ben Simmons’ upside as an offensive initiator. He is a point guard who can’t run pick-and-roll, because defenders go deeper than just under screens. He can’t play off the ball because no one needs stand within 15 feet of him. Simmons is very good and very young and will continue to be very good, but the jumper is a clear limiting factor on how good he can be without fundamental change.

So how does fundamental change occur for a jump shot? Well, you likely begin the off season by securing the services of a proven shooting coach, who then completely nukes everything you’ve ever known about jump shooting. He builds your shot up like you’re learning for the first time, starting with the very foundation of the skill. It’s all you do the entire summer—no 5 v. 5, just jumpers, jumpers, jumpers. After a few years, you may well have a functional jumper. Simmons’ jumper is a limiting factor, a serious one, but it’s theoretically correctable with dedication and time.

Now consider how “feel” and “IQ” are developed: thousands upon thousands of hours of playing basketball, likely built upon some sort of innate capacity for pattern recognition and whatnot. These are skills forged through years of obsession, not summers of admirable focus or even a couple thousand minutes of playing time in an NBA season. If you show no sign of them by age 22 or 23, you’ve simply run out of time to acquire them.

It would in no way shock me to see Brown beef up his ball-handling, to see him improve his shooting and progress toward the status of marksman, but it’s the mental side of the game where I cannot buy the necessary improvement. Without that improvement, he’s disqualified from a high-volume on-ball role, and with it the avenue to stardom all but a few players in the NBA take.

I don’t want any of this to be construed as “Jaylen Brown is bad.” He’s not. He’s a useful complementary wing. But I do want to be realistic about the value of a complementary wing. I don’t know what the exact number is, but it’s certainly not we’re-fashioning-our-future-around-you money, and that puts the Celtics in an unenviable position right now.

They’re on the clock, with the right to extend Brown from now through the night before the start of the season. Given a meager 2020 free agent class, the value of wings, league-wide perception of “upside,” draft slot bias, etc., it would be naive to assume Brown would take an extension worth much less than his maximum.

Assuming the Celtics aren’t willing to go to that number (the aforementioned five years, $170 million), they have to be ready for a few outcomes: 1) matching a four-year, $126 million maximum offer sheet for Brown in restricted free agency 2) losing him for nothing in restricted free agency, or 3) trading him.

Given my skepticism of Brown’s upside as an on-ball creator, option one does not appeal to me at all. Obviously, option two wouldn’t appeal to anyone, which leaves us with option three.

I don’t know how to go about option three, because I don’t know what’s out there or who wants Jaylen Brown. But I do know option three should be carried out sooner rather than later if the Celtics choose to go that route. If the extension deadline passes and the Celtics are trying to move Brown, opposing teams would possess a few dangerous pieces of information: that the Celtics had the opportunity to pay Brown the max and didn’t, and that their only other option to retain him in the future is to do so. That’s a prime situation for a team to call the Celtics’ bluff, wait it out, and dare the Celtics to match that $126 million offer sheet in July.

If it were me, I’d be canvassing the league right now, before the extension deadline is really looming. I’d use the threat of extending him to demand a haul. If no one bites, I’d try to extend Brown at a reasonable number, one he’d be insane to agree to. If the deadline passes, I’d hope someone blows me away with an offer in-season, while knowing that I can fall back on my right of first refusal in restricted free agency with an eye to leveraging that for assets in a sign-and-trade (like we saw the Bucks do with Malcolm Brogdon and Nets with D’Angelo Russell this summer).

It’s not a fun situation in which the Celtics find themselves. The model is supposed to be draft good players, retain them, and prosper. When contracts and roles and how all that siphons into team-building come into play, though, sometimes being good just isn’t enough.