With Jayson Tatum out for the season due to an Achilles injury, the Boston Celtics are no longer seen as strong championship contenders for the 2025–26 season. This change has sparked discussions about whether the team should focus on building for the future by leveraging key trade assets.
Bill Simmons of The Ringer floated a potential move: trading Sixth Man of the Year Payton Pritchard to the Houston Rockets in exchange for former No. 3 overall pick Reed Sheppard.
Simmons: Prioritize Trade Value Over Championship Run
On The Bill Simmons Podcast, Simmons suggested that Jayson Tatum’s absence could give the Celtics a chance to take a more strategic, long-term approach to reshaping their roster.
“If things fall apart quickly for Boston, who knows what could happen?” Simmons said. He proposed that the team might consider trading Payton Pritchard a strong bench contributor and capable spot starter for a developmental player like Reed Sheppard, if they believe in his potential.
The idea also ties into Houston’s current situation, as they look to fill the void left by Fred VanVleet, who is out with a torn ACL. Simmons pointed out that Pritchard could offer immediate stability at point guard for the Rockets.
Pritchard’s Trade Value Peaking
Payton Pritchard’s breakout performance last season has significantly boosted his value within the Celtics organization. According to NBA insider Jake Fischer, the 27-year-old guard is now considered “nearly untouchable” in trade talks behind only Jaylen Brown and Derrick White in terms of how difficult he would be to acquire.
Fischer wrote in The Stein Line that, aside from Jayson Tatum and Jaylen Brown, Boston is theoretically open to listening to offers for any player. However, both Pritchard and White are viewed as especially hard to pry away, due to their importance and value.
Adding to Pritchard’s appeal is his team-friendly contract a four-year, $30 million rookie extension signed in 2023 which makes him a cost-effective asset as the Celtics prepare for a season without Tatum.
Last year, Pritchard averaged 14.3 points, 3.8 rebounds, and 3.5 assists per game while shooting 47.2% from the field. He played close to 30 minutes per game and, despite starting only three times, delivered steady offensive production off the bench.
Sheppard’s Potential Fit
For the Celtics, pursuing a trade involving Reed Sheppard would be a bet on long-term potential. The 21-year-old guard is still early in his NBA journey and is playing under a four-year, $45.9 million rookie contract.
During a conversation with Bill Simmons, ESPN’s Zach Lowe weighed in on Sheppard’s value compared to Payton Pritchard. “They’re probably about equal, but Pritchard might have a slight edge,” Lowe said, noting Pritchard’s more affordable contract and remaining three years of team control. “Sheppard has more upside, but Pritchard just won Sixth Man of the Year.”
With Fred VanVleet sidelined, the Rockets are expected to rely heavily on Sheppard and Amen Thompson in the backcourt, giving Sheppard more minutes than he likely would have received on a healthy, playoff-focused roster.
Future Over Present
Despite Pritchard’s strong performance, the Celtics are in a tough spot without Jayson Tatum. Bill Simmons suggested that trading Pritchard now could bring back a younger guard more aligned with Boston’s long-term plans, while giving Houston a player who can contribute right away.
At the moment, Celtics leadership maintains that Pritchard remains a vital piece of their rotation. However, as the season progresses, Boston’s openness to shifting toward a future-focused strategy may ultimately influence whether a deal like this gains momentum.
