With Jayson Tatum sidelined for the season while recovering from an Achilles injury, the Boston Celtics are no longer viewed as prime title contenders in 2025-26. That shift in outlook has prompted speculation about whether the franchise should parlay one of its top trade assets into a move geared toward the future.
The Ringer’s Bill Simmons suggested one such possibility: trading reigning Sixth Man of the Year Payton Pritchard to the Houston Rockets for former No. 3 overall pick Reed Sheppard.
Simmons: Trade Value Over Title Push
On The Bill Simmons Podcast, the analyst argued that Boston’s situation without Tatum may open the door to opportunistic roster building.
“Again, it depends — like if Boston’s season goes off the rails fast, who knows?” Simmons said. “Part of maybe making yourself a little worse for this year would be turning Pritchard, a really good bench guy, borderline decent starter, into a project like Reed Sheppard. You’d have to really like Reed Sheppard.”
The suggestion also comes as Houston scrambles to replace Fred VanVleet, who suffered a torn ACL. Simmons noted that Pritchard’s steady hand at point guard could immediately plug that gap.
Pritchard’s Stock at a High Point
Pritchard’s emergence last season has elevated his standing inside Boston’s organization. NBA insider Jake Fischer reported in June that the 27-year-old guard is “close to untouchable,” ranking behind only Jaylen Brown and Derrick White in terms of trade difficulty.
“Boston is believed to be open to listening to any player on its roster not named Jayson Tatum and Jaylen Brown,” Fischer reported in The Stein Line. “I’d put Payton Pritchard and Derrick White right behind those two franchise cornerstones as extremely hard-to-get as well.”
The guard is also on one of the league’s most favorable deals. His four-year, $30 million rookie extension, signed in 2023, makes him both affordable and valuable as the Celtics navigate the Tatum-less season.
Pritchard averaged 14.3 points, 3.8 rebounds and 3.5 assists last year, shooting 47.2% from the field. He played nearly 30 minutes per night, despite starting only three games, and provided Boston with consistent offense off the bench.
Sheppard’s Potential Fit
For Boston, a deal centered on Sheppard would be about upside. The 21-year-old guard is still in the early stages of his career on a four-year, $45.9 million rookie contract.
Zach Lowe, speaking with Simmons, debated how Sheppard’s value stacks up.
“I think they’re probably about equal and Pritchard maybe edges him out by a nose because his contract is longer than I thought,” Lowe said. “He has three years left on his contract at a cheaper salary than Reed Sheppard. Sheppard’s got the intrigue. Pritchard just won Sixth Man of the Year.”
With VanVleet out, the Rockets plan to lean on Sheppard and Amen Thompson in the backcourt, giving Sheppard more playing time than he might have otherwise earned in his second year in a contending team.
Future Over Present
Even with Pritchard’s breakout, the Celtics face an uphill climb without Tatum. Trading him now, Simmons argued, could return a younger guard who better fits Boston’s long-term timeline while providing Houston with immediate help.
For now, Celtics executives insist Pritchard is a key part of the team’s rotation. But as the season unfolds, Boston’s willingness to pivot toward the future could determine whether such a trade proposal gains traction.
Celtics Urged to Trade Payton Pritchard for Rising Former No. 3 Pick