After yet another disappointing end to the Celtics’ season, there are a lot of questions that need to be answered. What went wrong? Is this core the best fit to win a championship? What will happen with Payton Pritchard and Grant Williams? All three of those questions need to be answered, but one uncertainty that trumps them all is the future of Jaylen Brown. He is eligible for a 5-year, $292 million extension.
To start, I believe the Celtics should try to get an extension done with Jaylen Brown. Though I think the max is too much, if they can get a five-year deal done in the range of $225-250 million, then I believe that’s their best option. But the question here is what if that isn’t the path that both sides want? What if the Celtics decide to move on or Jaylen Brown wants a fresh start somewhere else? With one year remaining on his contract, trading Brown this offseason would become necessary. The Celtics can not afford to lose him next offseason for nothing. Let’s look at three possible trades that the Celtics should consider in this scenario.
Heading West
Celtics Receive: C Jusuf Nurkić, G Anfernee Simons, third overall pick, Blazers 2026 first-round pick (top three protected)
Blazers Receive: G/F Jaylen Brown & G Malcolm Brogdon
The Trailblazers are looking for a blockbuster and to add a star next to Damian Lillard. For the Celtics, it’s a bit of a hard reset. They add a needed big man to the mix and one that can score the basketball. Anfernee Simons has dealt with injuries early in his career but has also slowly progressed into a quality scorer in the NBA. In addition, they add the third overall pick to add a new young star (ideally Scoot Henderson or Brandon Miller) and a future first-rounder that could turn out to be a steal with Lillard’s window closing sooner rather than later.
Brown & Udoka Reunite
Celtics Receive: G Jalen Green, C Alperen Şengün, fourth overall pick, Rockets 2027 first (top 10 protected)
Rockets Receive: G/F Jaylen Brown, G Payton Pritchard, & 35th overall pick
The Rockets and new Head Coach Ime Udoka add two guys he’s well familiar with. On the Celtics’ end, they make a similar style move to the deal above and do a bit of a hard reset. Jalen Green and Alperen Şengün are two young budding stars in the NBA that have already made adjustments to become quality scorers. In addition, the Celtics add the fourth overall pick and a future first from Houston.
Old Friends Complete a Three-Team Blockbuster
Celtics Receive: PF Lauri Markkanen, SF O.G. Anunoby, C Kelly Olynyk & 2026 first Round Pick (Via Cleveland OR Minnesota)
Jazz Receive: G/F Jaylen Brown, PF Grant Williams (S&T)
Raptors Receive: C Walker Kessler, ninth Overall Pick, 28th Overall Pick
With this trade, the Raptors look towards a rebuild as they ship off Anunoby for multiple assets. The Jazz and old friend Danny Ainge complete the first major deal towards their rebuild by trading for two players he drafted himself. This is a trade that would allow Brown to become the true number one in Utah. For the Celtics, they go a different route from the first two deals by adding two players that can help them win now. Added onto the deal, the Celtics swap Grant Williams for old friend Kelly Olynyk and add a future first-round pick.
The Best Deal
If the Celtics were to trade Jaylen Brown, they better make sure they hit on the trade. In my opinion, I’d focus on the Rockets deal among these three. Green and Şengün are growing players that can still keep the Celtics as a quality team in 2023-24, while it also gives them the best chance to win the deal overall. With the fourth overall pick, they could dream Scoot Henderson falls to them or they can attack one of the wings expected to go in that range. Make the right selection, and Brad Stevens could make the best out of dealing Jaylen Brown.
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