One trade the Boston Celtics should consider if Jaylen Brown contract talks break down

With the deadline for rookie extensions to be signed looming, the Boston Celtics have a Jaylen Brown-sized conundrum on their hands. If he wants more than what the team is willing to offer, Danny Ainge should consider this trade.

By virtue of being a playoff contender for five years running, the Boston Celtics don’t need to be hasty with any moves they make. Even if they kept to the status quo with their roster as it is, there’s a good chance they would be among the top three or four teams in the Eastern Conference.

But that is never the goal in Boston. Winning a championship is always the primary objective heading into every season. Last year, the team appeared primed to take the mantle of the top dog in the Eastern Conference with LeBron James heading west to Hollywood and Kyrie Irving and Gordon Hayward returning to join a team that was one win away from an NBA Finals appearance in 2018.

Instead, dysfunction and drama derailed them. Players hated sharing the same locker-room and nobody progressed besides Irving, who leveraged his high-usage season to earn a max deal so he could skip town and join the Brooklyn Nets.

Only a franchise with the cache and tradition could replace one All-NBA talent with another. Kemba Walker is now running the show, and he is joined by a cavalcade of rookies like Carsen Edwards, Grant Williams and Tremont Waters who appear ready to step in and contribute from the jump.

This is all to say that somehow, despite all of the issues the team faced last season, the Boston Celtics are in great shape (some would say better shape) heading into the 2019-20 season. All appears to be right with the most successful franchise in NBA history.

There is only one small hiccup–the reportedly stalled contract extension talks of Jaylen Brown.

Brown reportedly turned down a four year, $80 million extension. While Ainge denies the veracity of the report, it isn’t far-fetched to think that Ainge might have balked at paying Brown that much, given that he has yet to reach the pretty modest benchmark of 15 points per game.

Brown believes in his talents, and given D’Angelo Russell‘s recent max deal after making the All-Star team in his fourth season, he has every right to hold out signing a deal he feels would be below market-value. In a conversation with Marc Stein of the New York Times, he laid out exactly where his head was:

"“But to be honest, [extension talks are] really not overwhelming me or ruling my thoughts. I know what type of talent I have. I’m confident in myself. I’m confident in my ability.”"

There could be a serious number crunch next June when free agency kicks off. Brown isn’t the only free agent-to-be; Gordon Hayward has a player option he can opt out of for $32.7 million for the 2020-21 season.

Hayward is more likely to affect the Boston Celtics’ success this upcoming season. If he can return to All-Star form, the team is that much closer to title #18. If he doesn’t, his deal becomes an inconvenient albatross.

That makes Brown an easier asset to trade. In truth, Brown’s youth and potential are more valuable to an opposing team than a one-time All-Star who broke his leg less than a year following his first All-Star appearance.

Any team looking into acquiring Brown would likely be one that feels it is a year or two away from contending, and one that can also convince itself that Brown is the answer…which brings me to the perfect trading partner for the fourth-year Team USA forward: the Sacramento Kings.

Sacramento is loaded on the wings, but acquiring Brown would come at the cost of a fourth-year swingman in a very similar situation in Buddy Hield. Hield similarly wants the bag, feeling insulted by a four-year, $90 million offer.

You might ask yourself why the Boston Celtics would take on a guy who wants more money than Brown does, and the answer is simple: he deserves it more than Brown does.

Hield is a knock-down shooter who can score anywhere on the floor. He shot 43% from the 3-point line playing alongside De’Aaron Fox. With Walker, Hayward and Tatum assuming most of the on-ball duties in the starting lineup, Hield fits in perfectly as a catch-and-shoot specialist. He shot 50% on shots where he didn’t dribble.

A Brown-Hield swap could benefit both teams but the Boston Celtics still need to address their center position. While Daniel Theis seems to have earned Brad Stevens’ trust to be the starter in the early-going this season, Ainge would be wise to add more high-upside big men to solve their long-term depth issues.

That is where Harry Giles comes in. Giles is still on a rookie-scale contract and taking a flier on the former Duke Blue Devil could unlock a new element on offense, having proven himself as a capable scorer (seven points on 50% shooting in 14 minutes per game) in limited run. He could be gettable given the Kings’ frontcourt logjam with Marvin Bagley, Dewayne Dedmon, Nemanja Bjelica, Richaun Holmes, Harrison Barnes and Trevor Ariza all needing minutes.

Now in order to acquire the duo, Ainge would likely have to throw in draft considerations. A final deal may resemble something like this:

The Celtics and Kings swap guards looking for a monster payday, Boston acquires a high-upside big-man and the Kings get draft capital for players that might have bolted the team anyway.

A likely win-win for all.