To extend or not to extend: the future of Jaylen Brown

The off-season isn’t over yet. Even after waiving Guerschon Yabusele, there’s still some book keeping transactions that need to finished. Vincent Poirier is officially a Celtic, but Daniel Theis has yet to put pen to paper on his agreed two-year deal. Tremont Waters is ticketed for a two-way contract, but it’s not official official. The intrigue around Summer League standout Tacko Fall has not amounted to anything more than the Exhibit 10 look-see. For the most part, we know what Boston is going to look like going into camp, but there are still bigger questions looming.

Last week, Jaylen Brown told Boston Sports Journal’s Brian Robb that the Celtics have not reached out to him regarding a rookie extension. “The ball is in their court,” Brown said. Brown is entering the final guaranteed year of his rookie contract and if the he and the team that drafted him can’t come to an agreement before the start of next season, he’ll enter restricted free agency in 2020.

Historically, Danny Ainge almost never extends players coming off their first contract. Rajon Rondo was the last player to get one. In the 11th hour before the deadline, both sides struck a 5-year, $55 million deal. The circumstances were different though. The Celtics were just a year removed from their banner season, Boston was arguably better in 2009, and Rondo had nearly averaged a triple-double in the playoffs with Kevin Garnett out. Rondo was peaking and Ainge wasn’t about to break up a championship team.

At this point, Brown looks to be part of the foundation of the franchise and offering him a contract extension before the 2019-2020 cements him in. It’s a vote of confidence in the 22-year-old who has not just shown growth as a player, but has displayed promise as a leader as a Vice President of the NBPA’s Executive Committee. Fellow alumna from the 2016 NBA Draft have already been assured their places with their respective teams. Both Ben Simmons (drafted #1) and Jamal Murray (drafted 7th) signed max contract extensions of 5 years, $170 million.

So much of this comes down to--for lack of a better word--feelings. The Celtics undoubtedly want to keep Brown long-term. It’s just a matter of price and timing. In recent years, Ainge has tried to negotiate contracts with young players right up to the deadline. Both Marcus Smart and Terry Rozier received discounted offers that they passed up in the fall and allowed the market to dictate their value in restricted free agency. The question is, what does that year of uncertainty do to the psyche of a player?

It’s been surmised that when the Jazz did not offer a max deal to Gordon Hayward after his third season in Utah, he soured on the franchise. He went on to ironically sign an offer sheet in Charlotte (after also being recruited by Kyrie Irving in Cleveland) to play with Kemba Walker in 2014. The Jazz would match and retain Hayward, but the damage was done. Three years later, Hayward did not pick up his player option and joined Brad Stevens and the Celtics.

There’s no way to know if the Jazz playing hard ball with Hayward in 2013 affected his decision in free agency in 2017, but that’s the prickly dynamic with restricted free agency. Imagine spending the first four years of your career learning, developing, and growing up at the same company and then them telling you, “this is what we think you’re worth, but if you can find someone that wants you more, we might match it and bring you back anyway.”

On the other hand, as much as Ainge has earned his nickname “Trader Danny”--I’ve often wondered if “Traitor” would be more accurate--he’s also a pragmatist. Financially speaking, there’s no reason to make Brown his highest offer now. Anything can happen in a year and Ainge can offer him the same contract next summer. There’s also the added value of flexibility. This off-season saw a record number of sign-and-trade deals. With fewer teams with cap space and fewer free agents on the market in 2020, not setting a price tag on Brown could entice another team to make a deal; for example, the Celtics could make a move for Bradley Beal with Brown as the Wizards’ target.

Regardless of how it plays out, this is a “show me” season for Brown whether he’s guaranteed long-term stability now or rewarded next July. To his credit, he’s enjoyed steady progress over the last three seasons in less than ideal circumstances. He’s been at the center of trade speculation and criticized for not knowing what it takes to win a championship. Brad Stevens has praised Brown and teammate, Jayson Tatum, for their poise under this high level of pressure at such a young age. Next season, he’ll be even more of a focal point. As good as he’s been, he hasn’t shown that next level stuff that Simmons and Murray have as cornerstones in Philadelphia and Denver, but he’ll have that chance now.