The basketball world was rocked Monday afternoon by devastating news out of Houston: Rockets guard Fred VanVleet is expected to miss the entire 2025-26 season with a torn ACL. The injury delivers a gut punch to Rockets fans, who were riding high on championship dreams after a stellar second-place finish in the West last season and the blockbuster addition of Kevin Durant to an already electric young core.
VanVleet’s absence doesn’t spell doom for Houston’s title hopes, but it dims the spotlight on what promised to be a thrilling campaign. The Rockets, now forced to recalibrate, are likely to scour the market for a starting-caliber guard to fill the void. And through the lens of Boston Celtics fans, one name immediately leaps to mind: Anfernee Simons.
Simons, the 26-year-old sharpshooter, has been a fixture in trade rumors since landing in Boston as part of the deal that sent Jrue Holiday to the Portland Trail Blazers. For the Celtics, that trade was less about acquiring Simons and more about dodging the NBA’s second-apron penalties by shedding salary. Moving Simons and his $27 million contract could further ease Boston’s financial constraints, making him an intriguing trade chip.
But while Simons might seem like a natural fit, sources suggest Houston’s front office could have its sights set on a bigger prize: Jrue Holiday himself.
Holiday, a proven winner with championship pedigree from his stints in Milwaukee and Boston, brings a rare blend of defensive tenacity and offensive selflessness—qualities that could catapult the Rockets back into the Western Conference’s elite. His versatility and clutch play make him the kind of player contending teams dream of adding. For Houston, pursuing Holiday could be a bold swing to salvage their championship aspirations.
The idea of Holiday landing in Houston, however, is a bitter pill for Celtics fans to swallow. When Boston traded Holiday in June, it was a move born of financial necessity, with teams knowing the Celtics had little choice but to offload his contract. Portland, on the other hand, faces no such pressure. The Blazers hold the leverage in any potential deal, and Houston’s desperation to replace VanVleet could force them to pay a steep price.
A Rockets-Blazers trade for Holiday would likely demand a hefty package—perhaps a promising young player to balance the salaries, plus draft picks to sweeten the deal. Complicating matters, the trade couldn’t happen until December 14, when players like Houston’s Steven Adams, recently signed or extended, become trade-eligible. To make the financials work, the Rockets might need to part with key rotation players like Jabari Smith Jr., Dorian Finney-Smith, or even Adams himself. A third team could also be required to facilitate the deal, adding another layer of complexity.
Would Houston be willing to gut their depth for Holiday? It’s a high-stakes gamble, but one that could solidify their contender status. For Portland, the opportunity to extract maximum value for Holiday—far more than Boston received—would be a coup.
Celtics fans, meanwhile, are left to wonder “what if.” No one could have predicted VanVleet’s injury or the trade market it might ignite. Boston’s decision to move Holiday was pragmatic at the time, but seeing Portland potentially cash in on a deal the Celtics couldn’t wait for stings nonetheless. If the Blazers manage to flip Holiday for a haul, it’ll be a tough pill for Boston’s faithful to swallow, even as they cheer for their team’s continued success.
For now, the Rockets are left to navigate a season without VanVleet, and the trade winds are swirling. Whether it’s Simons, Holiday, or another surprise target, Houston’s next move could reshape the Western Conference race—and send shockwaves through the NBA.