The blockbuster swap that sent Anfernee Simons to Boston for Jrue Holiday looked like a calculated risk for both franchises. Three weeks into the season, it’s already a full-blown crisis for the Celtics—and a vindication for Portland.
Jrue Holiday, at 35, is torching his doubters in Rip City. The veteran guard has slid seamlessly into the Blazers’ backcourt, delivering lockdown defense, poise in crunch time, and just enough scoring to keep defenses honest. Portland’s front office gambled on championship pedigree over youthful upside, and the early returns scream “heist.”
Meanwhile, Simons’ Boston experiment is unraveling faster than a cheap sweater.
Forced into a microwave-scorer role off the bench, Simons is posting a career-low 14.8 points on reduced usage—numbers that would’ve been a quiet night in Portland. His playmaking, once a staple of 5+ assists per game, has evaporated under Joe Mazzulla’s motion-heavy system that prioritizes spacing over creation. The eye-popping 42% from three looks nice on paper, but it’s coming on catch-and-shoot looks rather than the pull-up daggers that defined his Blazers tenure.
Defensively? The concerns that followed him out of Portland have metastasized. Simons remains a traffic cone in Mazzulla’s switch-everything scheme, routinely targeted in pick-and-rolls and late-clock situations. The Celtics, already razor-thin on the wing, can’t hide him—not when their title defense hinges on suffocating perimeter D.
Boston shipped Holiday out precisely to duck the punitive second apron. Re-signing Simons at his next market rate—projected north of $25M annually—would slam them right back into luxury-tax jail. With his contract expiring in February, the Celtics face a binary choice: extract something in a trade or watch $27.6M walk for nothing.
“Boston wants to maintain financial flexibility… Simons gives them a large buffer to add depth,” wrote ClutchPoints’ Brett Siegel.
Translation: Simons is a depreciating asset in a seller’s market.
Rival executives know Boston’s leverage is dwindling. The longer Simons stays, the more his sixth-man production normalizes—and the less appealing he becomes to contenders seeking starters. Teams like Orlando, Detroit, or even a playoff-bound San Antonio could dangle a protected first or a pair of rotation players, but the Celtics can’t afford to wait until February’s 11th hour.
If no deal materializes, Boston may be forced to take back short-term salary (read: another expiring deal) just to avoid the cap hit. That’s not roster-building—that’s damage control.
Every Holiday chase-down block, every Simons benching, widens the gap in this trade’s ledger. The Blazers didn’t just shed a defensive liability—they acquired a culture-setter who’s mentoring Scoot Henderson and anchoring a playoff push. Boston, meanwhile, is learning the hard way that “three-point volume” and “three-point fit” are not synonyms.
The panic button isn’t blinking in Boston—it’s already been smashed. Unless the Celtics flip Simons for meaningful depth before the trade deadline, the Holiday heist will go down as the offseason’s most lopsided deal.