Leave it to Bill Simmons to stir up the trade market with a move that could reshape two franchises heading in opposite directions. On the latest episode of The Bill Simmons Podcast, the veteran NBA analyst floated an intriguing trade proposal that would send Derrick White to the Houston Rockets, a deal that, on paper, makes sense for both teams given where they stand early in the 2025–26 season.
Simmons’ proposed deal goes as follows:
Houston Rockets Receive: Derrick White
Boston Celtics Receive: Fred VanVleet, Tari Eason, 2027 Phoenix Suns first-round pick
The Rockets Finally Get A Point Guard
At first glance, it’s a bold move. The Rockets are off to an excellent start, sitting fifth in the Western Conference at 6–3, but they’ve struggled to maintain offensive structure since Fred VanVleet’s season-ending injury. With Kevin Durant serving as the team’s primary playmaker, there’s been growing concern that too much of the offensive load is falling on the 37-year-old’s shoulders. Simmons’ solution? Bring in one of the NBA’s most reliable two-way guards in Derrick White, a former champion and defensive ace who could immediately stabilize Houston’s backcourt.
White’s versatility is exactly what the Rockets need. He’s capable of running an offense, defending multiple positions, and hitting timely threes, all traits that complement Houston’s core of Durant, Alperen Sengun, and Amen Thompson.
While White has endured a sluggish start to the season, averaging 14.9 points, 3.5 rebounds, and 5.1 assists on 33.9 percent shooting from the field and 27.1 percent from deep, his defensive value and playoff experience make him an attractive upgrade for a team trying to leap from ‘good’ to ‘dangerous.’
The Celtics Get Assets And A Young Player
From Boston’s perspective, this trade might mark the continuation of a retooling phase. The Celtics have been underwhelming so far at 5–6, and Jayson Tatum is still recovering from his own Achilles issue. Their championship window has dimmed, and the roster, once the envy of the league, looks in need of a shake-up. White is rumored to be at the top of Boston’s trade list, given his value around the league and the front office’s desire to gather future assets.
The trade also works financially and strategically. VanVleet, who signed a massive deal with Houston last year, has been sidelined with a torn Achilles and is not expected to return this season. Moving him to Boston would effectively give the Celtics a placeholder contract and perhaps a reclamation project for 2026 if they decide to keep him. Meanwhile, Tari Eason, the 22-year-old forward, gives Boston a young, athletic defender who fits their long-term timeline.
The inclusion of the 2027 Suns’ first-round pick could be a difference-maker. With Phoenix’s long-term outlook uncertain, that pick could become a premium asset. The Celtics could even push for an additional future pick or pick swap from Houston, as the Rockets still remain one of the league’s most asset-rich teams.
This Deal Makes Sense For Both Teams
For Houston, this move would be about cementing their status as a contender. Head coach Ime Udoka previously coached White in Boston, which adds another layer of comfort and familiarity. Udoka knows how to maximize White’s defensive instincts and off-ball movement, and reuniting the two could instantly improve Houston’s half-court execution.
If the Rockets pull this off, it could push them into the upper echelon of the Western Conference and give Kevin Durant the reliable backcourt partner he’s been missing since VanVleet went down. For Boston, it would mark the beginning of a quieter rebuild, one that finally acknowledges the need for change.
