Is Jaylen Brown Worth Boston’s Gamble?

Shane Rhodes dives into the Boston Celtics’ decision to extend Jaylen Brown and depending on the up-and-coming swingman for the years to come.

Alan Draper profile picture
Sports Editor
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Danny Ainge is a gambler, only not in the typical sense.

Yes, Ainge does, on occasion, deal with money. It’s just part of the job. But, more so than cash, Ainge is often one to gamble on players, whether they are his own or on some other roster.

For better or worse, the Boston Celtics have got to where they are now via his dealings. He has seldom passed on the opportunity to improve the outlook of his team, whether it be now, in the future or both.

His opportunistic nature is evident in his process. In his quest to bring the Larry O’Brien trophy back to Boston, Ainge has wheeled and dealt around the NBA, operating as anything but risk-averse. He gambled with the Brooklyn Nets and won; he shipped out star guard Rajon Rondo and came away the victor. He even lucked out on a 5-foot-9 point guard, Isaiah Thomas.

And, in the end, Ainge gambled it all on Kyrie Irving. With him in the fold, Boston was one of the few teams in the league that had a true chance at the NBA title.

But, as the old adage goes, even the best-laid plans of mice and men often go awry.

A turn of bad luck combined with a divisive locker room pit Boston’s roster against one another, as the Irving gamble blew up in Ainge’s face. Now, with Irving and former Celtic Al Horford elsewhere, Ainge has taken another gamble: He has bet on his youth.

The pivot was an obvious one. With Horford and Irving gone and Boston strapped for cash, he didn’t have much choice. But, by a stroke of luck, Ainge and the Celtics stumbled into Kemba Walker. And, while his four-year, near $141 million contract may seem like a risk in-and-of-itself, it only serves as an insurance policy to another Ainge lottery ticket.

Ainge’s real gamble, in fact, was the fact that he bet the house — and then some — on Jaylen Brown.

In the rookie extension bonanza that has consumed recent weeks, Brown and the Celtics agreed to a four-year, $115 million pact just prior to the NBA’s extension deadline, the Celtics’ first of such kind since Rondo back in 2009.

Brown’s deal was almost certainly the right decision, given Boston’s precarious position. But, it may also have been their only decision, a necessary transaction rather than one predicated on Brown’s previous contributions. Many expected the two to continue their relationship beyond this season, but few expected, after the down year Brown had, that a continuation would come at that price tag.

Brown is talented, and Ainge should know that better than anyone (perhaps even Brown himself). But, among other rookie extensions, Brown’s was bested by only Ben Simmons, Jamal Murray and Pascal Siakam – budding, or in Simmons case, pre-anointed stars, each of whom was the recipient of five or four-year max extensions from their respective teams. The $115 million Brown is set to earn over the next four seasons bested the deals received by Buddy Hield, Domantas Sabonis, Dejounte Murray, Caris LeVert and a number of others.

But is Brown really worth that? Is Brown that star already, or could he, at some point, even become one?

On the open market, Brown’s value may have plummeted. The 23-year-old struggled throughout the tumultuous 2018-19 season, as his role seemed to change on a game-by-game basis and he strained his way to a 13-point, 4.2-rebound and 1.2-assist per game stat line.

A far cry from the player that pushed Boston to the Eastern Conference Finals just two seasons ago, Brown certainly didn’t play like a $115 million player. And there is no guarantee whatsoever that Brown could ever, or would ever, be that player again.

But to the Celtics, his contract should prove worth every penny.

Given their precarious position in the NBA hierarchy, Ainge, and the Celtics franchise to a larger extent, need Brown. Without Horford and Irving, Boston is dependent upon him – at least in part – whether they want to be or not and regardless of his price. Whether anyone outside Boston deems Brown worthy of the price tag or not is moot: Brown is worth the cost to Ainge and the team, while the $115 million price tag is certainly preferable to the alternative.

Were Ainge to short change Brown in negotiations, sour their relationship or worse, lose him to free agency, the Celtics would be stranded in No Man’s Land. Barring another stroke of luck, Walker, Jayson Tatum and others would be stuck with a roster that’s okay, but not good enough to compete for a title.

Ainge brought in Walker with the belief that they could compete for a title. Brown is a major part of that, and his extension is not only an affirmation of Ainge’s belief in Brown, but in the team itself.

Of course, a la the Irving debacle, this extension could blow up in Ainge’s face. If Brown is unable to take that next step in his development, Boston could find itself in the same position had the organization let him walk, only now would be strapped for cash because of Brown’s potential albatross of a contract.

But, again, Ainge is a gambler. So, if you believe in the talent, why not take the chance?

The Celtics clearly believe in Brown and, while it may be foolish, they are paying for the player they know believe he can become. If he can live up to the hype, Ainge and Co. would much rather see him do so in Celtic green, helping them win another championship, rather than flourishing for the opposition.

So, in the end, it doesn’t matter if Brown, in a vacuum, is worth $115 million. When Ainge extended the terms, he may or may not have been certain that Brown would live up to that price tag.

But, perhaps more importantly, Ainge knew Brown was his only chance to ensure a bright future in Boston.

He took the gamble, and only time can tell if it’ll be worth it in the end.

Alan is an expert gambling writer who works as one of the chief editors for Basketball Insiders. He has been covering online gambling and sports betting for over 8 years, having written for the likes of Sportlens,, The Sports Daily, 90min, and His particular specialisms include US online casinos and gambling regulations, and soccer and basketball betting. Based in London, Alan holds an MA in English Literature and is a passionate supporter of Chelsea FC.

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