Report: Celtics unlikely to offer Jaylen Brown an extension

Jaylen Brown’s extension date looms as a critical moment for a Celtics team that’s capped-out for the next two seasons. On October 21st, the C’s good fortune and wait-and-see approach stemming from the Nets trade expires. Boston will have to finally pay up for the talent they replenished through Brooklyn.

The Celtics will likely punt those negotiations to the summer. Brown previously stated that Boston has not reached out to him with a contract offer. According to Sean Deveney (now with Heavy), the “chance is pretty slim” that Boston will offer an extension before the deadline next month.

That establishes the most-intriguing contract standoff since Marcus Smart entered a restricted free agency limbo in 2018. Before that, the Celtics either had clear-cut extension candidates like Rajon Rondo, or circumstances that rendered departures like Kelly Olynyk and Terry Rozier’s inevitable. Other draft picks fizzled (James Young) or departed in trades (Al Jefferson and Ante Žižić ).

Brown’s situation compares most closely to Rondo’s. The Celtics scored Rondo on a five-year, $55-million deal in 2009 on a championship contender where he definitively fell behind the Big Three. Rondo’s first free agency would’ve coincided with the summer of LeBron James, Dwyane Wade and Chris Bosh.

A secondary contributor last season, Brown emerged with 13.8 points per game on 50% shooting in his final 21 regular season games. He grew through a bench role, was a major contributer to an East Finals run, then returned to the bench after immense early-season struggles last year.

That non-linear career arc creates a difficult extension forecast. Typically, second deals offer substantial pay raises to successful top draft picks like Brown. That commitment projects growth. Brown obliterated the 76ers in 2018 and he’s clearly a starting-caliber player, but nothing’s really signaled All-Star appearances in his future. The Timberwolves hurt themselves offering Andrew Wiggins a max without clear indication he’d become that player. Danny Ainge faces a similar decision.

Brown’s camp holds legitimate leverage to ask for a max contract, too. The Celtics don’t have a chance to pick in the top-5 for the foreseeable future (unless the Grizzlies pick converts in 2020). Boston is capped-out between Gordon Hayward’s deal (ends with 2020-21 option), Jayson Tatum’s impending payday (extension-eligible in October, 2020) and Kemba Walker. The only reasonable way to spend their money next summer is on Brown.

The Celtics will be hard-pressed to get a discount akin to Smart in the market either. With Draymond Green and Eric Gordon extended — and Anthony Davis likely staying with the Lakers (for now) — Brown could become one of the top free agents. Considering his age and upside, he could command a max offer sheet interest over older players in Andre Drummond, DeMar DeRozan and Mike Conley (all three have player options for 2020-21).

Brown could feasibly find a massive payday without a breakout season. Boston’s hope is that another large spending summer last summer challenges teams to create over $20-million in space. Factoring in options and cap holds, no team has any cap room for next summer yet.

We know that’s always maneuverable though, with the most likely candidates to create room being the Heat and Kings. The Hawks project to have the most space, with a young core they’d like to supplement. Brown is an Atlanta native. The Raptors could offer a calculated sheet to push Boston.

That sets up a critical season for both sides. The Celtics enter with uncertain contention status, but also signed a long-term star who came to win. Brown gets his prove-it situation. In the end, they both win if he emerges as a front-line contributor.

The ideal outcome would be a campaign that places him close to All-Star consideration. A five-year maximum contract with Boston would pay Brown roughly $169-million over five seasons, starting at $29.3-million in 2020-21 and finishing at $38.6-million in 2021-22. Even discounted versions of that thrust Boston into the luxury tax.

If Boston’s winning, that’s great. If not, it sets up a complicated negotiation. Teams squeezing their restricted free agents previously led to lasting awkwardness. Hayward serves as a prime example, earning his pay raise with the Jazz through a Hornets offer sheet, then leaving for free agency. Brown could earn his second deal the same way.

In this era of constant free agency, this deal establishes the foundation for Brown’s future. If the Celtics view him as their long-term star, they’ll need to make Boston his comfortable home.

For now — whether due to potential injury or simply waiting to see what he accomplishes in 2019-20 — they’ll wait and see.