Jaylen Brown’s bag and the art of assessing NBA contracts

Jaylen Brown agreed to a sizable contract extension with the Boston Celtics on Monday. He’s now guaranteed $103 million over the course of the next four seasons (starting after the current campaign is complete), with the potential for his total compensation to reach as high as $115 million via a mix of likely and unlikely incentives.

In ponying up for Brown, the Celtics have placed a bet on his development. The rangy wing with tantalizing athleticism is already capable of consistently creating a positive impact on both ends of the court, but hasn’t demonstrated a star-level quality of play that warrants a deal that will pay him more than $20 million in its first year and over $28.5 in its final two. Such sums of money are typically reserved for particular player archetypes.

Clear superstars are the most obvious and likely players to be lavished with cash. No one will ever complain that the likes of LeBron James, Steph Curry, or Kawhi Leonard are overpaid. In fact, the league’s salary cap keeps them from actually being paid what they’re worth. A max or near max deal to a top-10 caliber player is a ludicrously valuable team building advantage.

It’s exceedingly unlikely Brown develops into that level of star, even if he grows into his fullest potential. But that doesn’t mean Boston was unwise to pay him handsomely. MVP types are incredibly rare. There aren’t enough of them for every team to have one. The Celtics put together a plan to try to land just that type of player in their nearly half-decade long pursuit of Anthony Davis. It didn’t work, and now they’re doing the best with the options available to them.

There are other kinds of players that tend to warrant big money beyond the clearest of clearcut stars. Primary offensive engines - a la James Harden, who is so good at this role that he qualifies for the clear cut star distinction - and versatile bigs that can anchor a defense - like old friend Al Horford - are prime examples. Brown is neither of those either. And as such, some have cautioned against extending him.

There is some logic there. If the internet has taught us anything, it’s that large deals for players like Harrison Barnes, Otto Porter, and Andrew Wiggins are to be derided. If you think Brown fits that category of player, then his new contract is indeed something to be questioned. But Brown is a significantly better athlete than both Barnes and Porter, and a far more dedicated worker than Wiggins.

He’s shown a capacity for growth beyond what any of that trio of allegedly overpaid wings has demonstrated throughout their careers, and has proven himself capable as a rotation piece on a contender on multiple occasions. There’s also a separate matter of assessing just how harshly big deals to wing players need to be critiqued, and an even larger question at hand of whether or not we are assessing the value of NBA contracts in the most effective manner possible.

There are two distinct, though related, considerations to be made here. The first is the propensity to value distinct skill sets. Scoring at a high volume efficiently, for example, is believed to be one of the more unique abilities a player can possess. Those who are capable of doing so cost a premium to acquire. There is an unquestionable logic to this train of thinking. That scarcity drives price is a reality of markets writ large, not just the NBA.

But what is to be made of offensive maestros that aren’t quite good enough to raise their teams to championship contention?

Let’s use a few of Brown’s peers as examples: Jamal Murray, D’Angelo Russell, and Brandon Ingram all come to mind immediately. Each is immensely gifted offensively and roughly at the same point in their career trajectories as Brown. Murray and Russell have max contracts. Ingram is a year away from potentially landing one of his own.

Photo by Nathaniel S. Butler/NBAE via Getty Images

There’s more of a chance that none of those three will ever be good enough to fill the role their skill sets dictate on a championship-caliber team than Brown will his. For every Kawhi Leonard or Kevin Durant, there are three or four DeMar Derozans, Kyrie Irvings, or Zach LaVines - players who simply aren’t good enough to be the best player on a title team but are paid exorbitant amounts of money because they put the ball in the hoop.

Meanwhile less heralded players like Danny Green - who has started on multiple title winning teams - are resigned to signing deals for comparative peanuts. Replicability of skills is the reason most often cited for such a reality. Star role players are more easily replaced, and cap space is better utilized chasing after talent that has the potential to provide less commonly available abilities. Or at least so goes the conventional thinking.

There’s a dissonance to such reasoning that occurs when players top out as merely very good, however. Is having Russell eating up more than $20 million of your cap really preferable to a player like Brown if the former never blossoms into a full-blown focal point of a top-tier offense? There isn’t a lot else Russell can offer. Brown has already proven an ability to stay on the court against any match up at any level of play. Is that not money better allocated?

Perhaps the answer here is that both players are overpaid. More likely - and is almost always the case - context matters (this is our second of the two considerations). If a team is simply looking to participate in the postseason then Russell, or another of his ilk, might be their man. He can provide enough of a boost to an offense to raise a team’s floor to something close to cracking the Playoff mix in a way that a player like Brown can’t.

For a team contending for a championship Brown is a more natural selection. Playing in The Finals requires rotation pieces with as few exploitable flaws as possible. Brown fits that bill. Whether or not allocating the amount of resources Boston just did to keep him on the roster makes sense would have to be determined entirely by the rest of the team surrounding him.

The Celtics are in an interesting middle ground between these two poles. They’re not a legitimate threat to win a championship, but they’re also not just seeking to simply make it to the postseason, in the present or the future. They have title aspirations. Which is what makes assessing Brown’s extension particularly challenging. If Boston wants to contend in a meaningful way in the future and not regret ponying up for Brown then one of two things needs to happen.

Either Brown needs to develop into an All-Star or the Celtics need to make sure they have enough offensive firepower and defensive acumen beside him to make being a super solid, but unexceptional, two-way wing a role that is worth paying for. Neither outcome is an impossibility, particularly if one is bullish enough on Jayson Tatum as a primary option.

And the fact of the matter remains that Brown can function at the game’s highest level, both now and in the future. If he doesn’t develop enough as a player then the financial restrictions his contract places on the team may very well keep Boston from being able to add the high-level pieces it needs to make his skill set worth its new price tag, but there is real value in knowing that he can be a contributor right now and in whatever iteration comes next for the Celtics.

Brown is good and getting better. That’s worth paying for.