Would the Boston Celtics Trade Jaylen Brown for Ben Simmons?

Chris Szagola/Associated Press

The latest team to enter the Ben Simmons trade watch is the Boston Celtics, as first reported by The Athletic on Monday.  

It would seem highly unlikely for Simmons to join the Celtics unless Boston’s outgoing package sent All-Star wing Jaylen Brown to join Joel Embiid in Philly.

That’s not to say that the two sides discussed Brown in significant detail, but he would be the Celtics player—an All-Star with proven playoff experience—that Sixers president Daryl Morey surely told Boston brass he coveted in exchange for Simmons. Morey has been direct with interested teams about the players he’d move Simmons for, and league personnel also assert Jayson Tatum remains entrenched as Boston’s true cornerstone.

Boston now joins ​​Cleveland, Detroit, Houston, Indiana, Minnesota, Portland, Sacramento, San Antonio and Toronto as the known teams that remain engaged with Philadelphia. But the Sixers have received very few firm offers for Simmons at this juncture, sources said, and have mainly outlined two- and three-team frameworks they would accept.

In those conversations, Morey has long maintained his team is only open to moving Simmons for a player like Brown, one that keeps the Sixers’ title chances starring Embiid at the same high level as it does with Simmons, despite the Defensive Player of the Year runner-up’s obvious interest in playing elsewhere. 

The team’s 8-2 start under Doc Rivers has alleviated any potential pressure that a slow start, such as Boston’s, could have led ownership to encourage Morey’s front office to move Simmons. A few interested teams were certainly hoping that would be the case, just as Morey was hoping for that to unfold in Portland. 

To acquire Brown, Philadelphia would likely need to include draft capital with Simmons and perhaps an additional player. As evidenced in their pursuit of James Harden, the Sixers are willing to pay for an incoming All-Star they deem is an upgrade over Simmons.  

In those conversations with Houston, the Sixers were said to have discussed each of Tyrese Maxey and Matisse Thybulle in addition to Simmons and multiple future draft picks. Today, though, Sixers staffers have been encouraged by the early returns of Tyrese Maxey as a starting guard, and the 21-year-old would seem to be untouchable in any Simmons trade conversation that didn’t bring back an All-NBA guard such as Damian Lillard or Bradley Beal. 

Perhaps Maxey and Brown could share ball-handling duties similar to Kyle Lowry and DeMar DeRozan’s collaboration all those years in Toronto, or the recent pairing of Jrue Holiday and Khris Middleton in Milwaukee. Brown’s defensive prowess could support Embiid on the perimeter. 

Any move including Brown likely isn’t coming any time soon, however. When push ultimately comes to shove, the Celtics would seem far more inclined to offer a package centered around Marcus Smart and Robert Williams III, which was the often-rumored framework of Boston’s initial efforts to land Aaron Gordon before last year’s trade deadline. 

But a three-team framework, sending Smart and Williams and picks for another All-Star to reroute to Philly, would seem to be the one possible route for Boston to land Simmons without sacrificing Brown. Philadelphia has similarly encouraged teams such as Minnesota and Indiana to acquire a player the Sixers value that would be equal to Simmons’ impact on the team’s title window, league sources told B/R. 

Smart invited questions about the Celtics’ young core after criticizing Brown and Tatum’s ball dominance following a recent loss to the Chicago Bulls. Smart’s dissatisfaction with Boston’s offensive rhythm dates back to last spring, according to league sources, when Celtics staffers also recognized Smart’s displeasure seeing his name floating in trade whispers.

Despite that, Smart accepted a four-year, $76.5 million contract extension this offseason. Smart is the longest-tenured Celtics player, the first draft pick of Boston’s rebuild from the Big Three era, and has long been a favorite of Brad Stevens and the team’s front office. 

It feels like part of why his name is often mentioned in trade rumors, rather than completed deals, has come from Boston holding a high asking price for Smart that interested teams have not met. 

But now the Celtics stand at just 4-6, with their next six games coming against Eastern Conference contenders or teams with records of .500 or better. New head coach Ime Udoka was hired with the goal of returning this team to the postseason, and front offices around the league are expected to increase trade chatter in the lead up to December 15, when the majority of players who signed new contracts in free agency first become eligible to be traded. 

That still appears to be the earliest date Simmons will be moved, whether to Boston or any other interested suitor. 

There’s belief among rival executives and league personnel that Simmons could even remain on the Sixers roster past the trade deadline. Morey’s asking price remains higher than any rival front office has been willing to match. The weekly updates on Simmons’ status with the team and whether he’s being fined have had no impact on his trade value among rival executives.  

But there’s now been a moment of flirtation with Boston, and every deal in the NBA stems from a first phone call. Back in December 2014, for example, Boston called Phoenix about trading for Isaiah Thomas. It was the first brief exchange that inevitably led to the Celtics nabbing Thomas a few minutes before the 2015 trade deadline that February. 

For now, Philadelphia officials will remain steadfast in their hopes that Simmons will return to play and help the Sixers contend for a championship until a trade offer they find suitable arrives. That will either require Simmons and Philadelphia to play past this dark cloud together or another team’s stumble to force that front office’s hand, leading to them pushing more chips into the middle. Maybe that team will be Boston, but this story has a long way to unfold. 

Jake Fischer covers the NBA for Bleacher Report and is the author of Built to Lose: How the NBA’s Tanking Era Changed the League Forever.