Trading Guard To Rockets ‘Makes Sense’ For Celtics, Says Bill Simmons

With the Houston Rockets losing Fred VanVleet to an ACL injury, they might be calling the Boston Celtics soon about a possible trade. Boston’s “gap year” status without Jayson Tatum makes them an intriguing trade partner for any contender, the Rockets included. 

Would Celtics president of basketball operations Brad Stevens trade Derrick White to Houston? Almost certainly not. But Payton Pritchard could be considered a more likely scenario, as The Ringer’s Bill Simmons discussed during a new episode of The Bill Simmons Podcast.

Simmons believes that a deal sending Pritchard to Houston and former No. 3 overall pick Reed Sheppard to Boston could benefit both teams.

“Payton Pritchard … weirdly lines up with Reed Sheppard’s salary,” Simmons said. “So part of the question for me is, if I’m doing a trade value list, where is Reed Sheppard? He’s certainly not in the top 50. Is his trade value higher than Payton Pritchard’s? Is it lower? Is it the same? I have no idea.”

“I really like Payton Pritchard (in Boston), but I also like that move for the Rockets,” Simmons continued. “I actually think that’s the answer in this (VanVleet situation) because it’s a little lower-risk. It makes sense for Boston because you would only do it if you got a better asset than him as a player. Then you keep (Anfernee) Simons for the year, and you have this asset that maybe you could flip back.”

Pritchard is a proven commodity in the NBA — he won Sixth Man of the Year last season and contributed to Boston’s 2024 title. Sheppard isn’t proven, but he might have a higher ceiling than Pritchard, something that could intrigue Stevens and the Celtics.

Simmons wasn’t fully accurate about the salaries matching up for Pritchard ($7.2 million in 2025-26) and Sheppard ($10.6 million), and a straight-up trade wouldn’t work if it were attempted today.

The alternative stance on all of this is that Pritchard, given his incredibly cheap salary ($23.3 million owed over the next three seasons), is a player worth holding onto under practically any circumstances beyond packaging him in a blockbuster deal for a top-15 player, a scenario that the Celtics with their salary situation aren’t in any position to do.

While a Sheppard-Pritchard deal is creative, it doesn’t make as much sense for Boston as Simmons suggests, mostly because Pritchard is more valuable (and far more of a bargain) than Simmons is acknowledging.

Pritchard represents one of the NBA’s best-valued contracts at the moment, and the Celtics would be wise to keep him during his prime years.