Ten years ago the Boston Celtics awarded Rajon Rondo with a five-year, $55 million deal that was partially done, in the words of his agent Bill Duffy, “to promote continuity.” Duffy knew Rondo’s perplexing behavior might combust in a different locker room, and the Celtics knew that failure to reach a deal could alienate their budding franchise point guard, something they had to avoid with a championship window cracked open. It was a unique situation that worked for the team and the player.
A decade later, the Celtics found themselves in a faintly similar situation with Jaylen Brown. Before his four-year, $115 million ($103 million is guaranteed) deal was signed, the same level of pressure that applied with Rondo wasn’t quite there, but the benefits of getting something done outweighed everything that could go wrong had they let this hang over the season, one year after they were the face of NBA dysfunction. Instead of waiting the year out and letting Brown hit restricted free agency — where his hometown Atlanta Hawks will have more than enough cap space — Boston locked the former No. 3 overall pick up at a steep price that better reflects future potential than past production.
The opportunity cost was low, too. The Celtics won’t be players in free agency for quite some time. What this does is afford them the type of stability and control that appeals to every front office. And in a big picture sense, the money is more than an investment in everything Jaylen does on the court over the next four years. It will also enter the room whenever both parties next sit down to negotiate his third contract. There’s a lot of good will baked into that $100+ million. Brown was paid like a star even though he is no such thing. The Celtics hope their conviction will pay off in more ways than one.
(At the other end of the spectrum, Brown’s contract also doubles as a hefty trade chip, should a disgruntled star emerge over the next few years. That’s not the reason Boston made this deal, but the reality of the NBA is if Karl-Anthony Towns becomes available the Celtics will not hesitate to put Brown in the offer — something they weren’t inclined to previously do when Kawhi Leonard was on the block.)
Several front office executives polled for this story think the Celtics might have paid too much for Brown, though not at an amount that’s detrimental. The tax will be a concern in 2020-21 and beyond, with Gordon Hayward opting into his contract and Jayson Tatum’s max extension in the pipeline. They understand Boston’s motivation for getting Brown’s deal done when they did. That’s the cost of trying to contend. It makes sense to pay an athletic, versatile wing who can shoot threes, create space for himself in the mid-range, and finish strong through contact.
His game is all urgency, strength, and flair, with a pinch of growing technical precision sprinkled on top. The Celtics would either pay him this amount now, in a show of faith, or wait out the year, let Brown hit restricted free agency at the age of 24, and then match a possible max offer sheet. They could also trade him during this season — not happening unless it’s for a star — or even lose him for nothing/risk him signing a funky offer sheet, and embroil themselves in an ugly spat that was avoidable from the start. To say nothing of the signal it would send to every other young player on the team, this wouldn’t be great.
The Celtics like Jaylen a lot. That’s what this deal comes down to. But what interests me most is what it says about his potential. He’s now entering that critical stage of any promising career where most of what he can’t do is more noticeable than whatever he can. That’s not a bad thing, but a reminder that expectations in two years will be light years from where they were four months ago. The stakes will soon align with production instead of upside. Context matters here, but Brown failed to make a statistical leap in his third year, has never recorded a PER above league-average, and does not (can’t?) make plays for others.
We know growth isn’t linear, though. Swapping Kemba Walker for Kyrie Irving and injecting a healthier Hayward (the cutter/playmaker/spacer he was in Utah) into the mix should help Jaylen reach a higher level as he rounds out his game and makes organic strides in areas that need to improve.
Long term, the good news for Boston is Jaylen doesn’t shy away from big moments. He was their closest thing to a guiding light through the nightmarish haze of last year’s playoffs — whirling up and down the court with an unflinching chin — and averaged over 18 points per game the previous year, when the Bucks, Sixers, and Cavaliers didn’t have much of an answer for him. His numbers over the past two postseasons are pretty great for someone so young — throw in the fact that he regularly does stuff like this and it’s clear players like this don’t grow on trees:
Zoom out and the perspective on this extension is similar to many others signed over the past couple months. Teams worry about getting burned by fourth-year leaps and don’t really want to see their own young talent reach restricted free agency, where they lose a degree of control. At the same time, only four teams are on track to have max cap space next summer: the Knicks, Grizzlies, Hawks, and Cavaliers. Maybe Jaylen has interest in playing for one of those teams. Maybe he doesn’t. None are super great for someone who’s made the playoffs in every season of his career, and there’s no guarantee any even like what Brown has to offer. In other words, both sides were motivated to get a deal done.
This circles us back to Duffy’s comment from the top. The job of an agent isn’t only to make their client as much money as possible, but to put them in positions where they can succeed. It’s been up and down in several ways, but for the most part Boston is a great spot for Jaylen to grow.
He knows the coaching staff, system, and after spending the bulk of his career sacrificing numbers for the sake of a team that never reached the Finals, sees an opportunity to shine in the very near future. How bright, exactly, is a question worth asking. Is he a perennial all-star like Jimmy Butler or Paul George, or closer to Otto Porter and Andrew Wiggins? Can he be a top-15 player? Jayson Tatum’s sidekick on an NBA champion?
The chance to find out in an environment that’s judged by rings and banners makes this a win-win for both sides. Each one should be excited about what they may discover.