At the moment, Jaylen Brown represents one of the tougher evaluations in the NBA. His talent is obvious, but his role on the Celtics has been less clear, or at least less consistent, and consequently we’ve only seen stints of the All-Star player most people believe he’s capable of being. 

At his best, Brown was the best player on the floor for significant stretches during Boston’s unlikely run — without Kyrie Irving and Gordon Hayward — to Game 7 of the 2018 conference finals. But he was nowhere near that player for much, if any, of last season, early on in which he lost his starting spot to Marcus Smart. 

Now Brown is entering his fourth season, which makes him eligible for an extension should the Celtics decide to offer one between now and Oct. 21. But according to Sean Deveney of Heavy.com, that isn’t likely to happen. From Deveney:

According to a league source, “the chance is pretty slim” that Brown signs a long-term deal with the team in the coming month. Around the league, the expectation is that Brown and the Celtics won’t come to a deal.

Three players from Brown’s 2016 draft class have signed extensions prior to the expiration of their rookie contract. Two of them, Jamal Murray and Ben Simmons, got four-year, $170 million max deals form Denver and Philadelphia, respectively. The third, the Nets‘ Caris LeVert, extended for three years, $52 million earlier this summer. 

That’s almost a $120 million gap between what Simmons and Murray got and what LeVert got, and it’s reasonable to think Brown would fall somewhere in the middle, something in the neighborhood of $80-$90 million over four years. But Brown, who doesn’t use a traditional agent to represent him, likely believes he’s closer to a max player than he is to someone like LeVert, and again, he’s at least shown flashes of being right. Heck, Andrew Wiggins got a max extension from Minnesota after three years, and Brown might be twice the player Wiggins is. 

If no extension is reached by the Oct. 21 deadline, Brown will become a restricted free agent next summer. That’s where this gets risky for the Celtics, who would have the right to match any offer Brown gets on the open market but might end up being held to the fire. It only takes one team to offer a poison pill max, or something close, and suddenly Boston would have to grapple with paying close to $180 million for a player they maybe could’ve gotten for, say, $120 or $130 million. Who knows if Brown would accept anything less than the max this summer, but so far, there in no indication Boston is even interested in making an offer. 

The Celtics are notoriously stubborn when it comes to extending players on rookie deals. Two summers ago, Marcus Smart wanted something close to $80 million for his extension, but Boston refused, and when Smart couldn’t get anyone to make a big offer as a restricted free agent the following summer, the Celtics wound up getting him for $52 million. They’re making a similar bet on Brown, that they will be able to get him for less next summer. 

That’s dicey. Both Brown and Smart are versatile, coveted defenders, but Brown has a much higher offensive ceiling and should thus command more lucrative offers, perhaps even independent of how he fares this season. At 23 years old, his potential alone is likely still enough to get him pretty handsomely paid. 

So the Celtics are likely back in the same spot: Pay him now or pay him later. Another year of information is valuable, but to end up losing Brown would sting exponentially. For years they have kept Brown on the “forget about it” list any time trade rumors have emerged. They could’ve made a run at Paul George when he wanted out of Indiana. They could’ve gone harder after Kawhi Leonard. They could still move for Bradley Beal, and they may end up trying to do that before season’s end. But Brown would almost certainly have to be part of a package to lure that kind of player, and the Celtics have never been willing to part with him. 

That would be a lot of big-time players to potentially pass up for a player you balk at paying and allow to sign elsewhere anyway. In that way, through opportunity cost alone, the Celtics have already invested a great deal in Brown. You could make the case that they WANT to eventually pay Brown big money because that will mean he has succeeded at a high level, and they NEED him to succeed at a high level to validate their belief and loyalty to this point. 

The problem is there still doesn’t appear to be a completely clear plan for how Brown will be utilized, let alone maximized, moving forward. The Celtics are wing heavy, with three of those wings effectively vying for two starting spots. Entering the 2019-20 season, Kemba Walker, Jayson Tatum and a big man, perhaps Enes Kanter, are locks to start. That leaves Hayward, Smart and Brown for the final two spots. 

Boston could play this the same way the Warriors did with Andre Iguodala and Harrison Barnes in 2014-15, when Iguodala, a very similar player to Smart, was probably a better player than the younger Barnes but was also better equipped, if only from a mental standpoint, to come off the bench. The Warriors started Barnes and got the best out of him while Iguodala was going to do his thing either way. 

For similar reasons, Smart is probably the best bet to come off the bench. Or if not Smart, perhaps Hayward. But reports throughout the summer have indicated Hayward is on the verge of rediscovering his own All-Star form. Even if Smart does begin the season on the bench, as previously mentioned, that same setup didn’t last two months last season before Smart supplanted Brown. 

In the end, Brown has to find his own way, whether that’s as a starter or bench player. The Celtics figure, at least, to be a happier team this season with Kemba’s galvanizing attitude replacing Kyrie’s equally alienating one, but from a pure basketball standpoint, Walker is still going to have the ball as much as Kyrie did. Brown is not going to get the freedom he got back in those 2018 playoffs. Boston isn’t going to cater to him even the way it figures to do for Tatum. 

That said, there are scouts who believe Brown has the potential to be every bit the player Tatum can be, but he might need to be on a different team become that player. Tatum, on the other hand, is going to get every opportunity to succeed in Boston, and if he does that, the Celtics are a good bet to offer him the max extension next summer that they’re apparently not willing to offer Brown this summer. 

Any way you slice it, this is a huge year for Brown. Again, he’ll get good offers on the open market no matter how he plays this year. His two-way talent is obvious, and there will be some team, if not multiple teams, willing to bet that a change of system and situation is all it would take to bring the best out of him. But to get the full max offer he believes he’s worth, he’s going to have to turn a lot of that potential into consistent reality. Perhaps even make, or at least flirt with, the All-Star team. He’s plenty capable. Boston knows it. But for now, it also appears they intend to make him prove it.