Bill Simmons ‘Semi-Devastated’ Celtics Didn’t Make This Trade

By all accounts, the Celtics are keen on signing Jaylen Brown to a supermax contract extension that will keep him in Boston for years to come.

But if Brad Stevens and company were looking to shop the two-time All-Star, Bill Simmons knows the deal he would have liked to see the Celtics make.

Simmons recently witnessed Jabari Smith Jr. put up a combined 71 points across the Rockets’ first two NBA Summer League games. “The Ringer” founder would have signed off on Boston moving Brown in exchange for the third overall pick last year as well as another high draft selection.

“I was semi-devastated ’cause I do feel like if the Celts had pushed hard for the Jaylen (Brown) for Jabari and No. 4, some version of that … That was probably the most logical Jaylen trade,” Simmons said on his podcast, as transcribed by Sports Illustrated.

That hypothetical trade package obviously is off the table now that the 2023 draft is in the books. The Rockets used the fourth overall pick on guard Amen Thompson, who will join an exciting young core in Houston that also includes Smith, Jalen Green and Kevin Porter Jr. It also should be noted the up-and-coming Rockets now are coached by Ime Udoka, who led the Celtics to the NBA Finals in his lone season at the helm in Boston.

Brown trade fodder probably is a useless exercise anyway, as reportedly only a few details separate the Celtics and the 26-year-old from reaching a long-term deal.