The Boston Celtics are teetering on the edge of a financial and strategic maelstrom, with their blockbuster offseason trade for Anfernee Simons already sparking talk of another seismic move. The dynamic 27 _
-year-old guard, acquired in the deal that sent Jrue Holiday to Portland, could be flipped before ever donning the iconic green and white, as the Celtics scramble to dodge a crippling luxury tax bill that threatens to reshape their roster and future.
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Simons, a sharpshooting guard with a knack for offensive creation, was brought in to help fill the void left by star Jayson Tatum, who is set to miss the upcoming season. With a $27.7 million salary in the final year of his contract, Simons offers Boston a potent scoring punch and youthful upside. At just 27, he’s still blossoming into a potential cornerstone, capable of generating buckets in crunch time—a critical need for a team now lean on star power. Yet, the Celtics’ front office is reportedly exploring options to reroute Simons in a desperate bid to ease their salary cap nightmare, with CBS Sports’ Brad Botkin predicting the move is all but inevitable.
“Now, the move I do believe the Celtics will make is to flip Anfernee Simons,” Botkin wrote. “With the Celtics trying to duck under the luxury tax, they are exploring the idea of rerouting Simons before he ever suits up as a Celtic.” The financial stakes are staggering: Boston’s luxury tax bill looms like a guillotine, with Simons’ hefty salary pushing them deeper into the red compared to Holiday’s more manageable, multi-year deal.
The Celtics have already made waves this offseason, parting ways with Kristaps Porzingis and letting Luke Kornet walk in free agency while trading Holiday. These moves signal a team in transition, grappling with the delicate balance of staying competitive while managing a ballooning payroll. Losing Tatum’s scoring prowess only heightens the urgency to find offensive firepower, making Simons a tantalizing asset—yet one the Celtics might not be able to afford to keep.
So, what’s next? Flipping Simons could open doors to address another glaring need: a starting center. With Al Horford expected to depart, Boston’s frontcourt is dangerously thin. A trade could see Simons, on his expiring deal, dangled to cap-rich teams like the Brooklyn Nets, who might absorb his contract for a draft pick or other sweetener. Botkin also notes potential interest from the Los Angeles Clippers or a multi-team deal where Brooklyn serves as a facilitator. Such a move could land Boston a rim-protecting big man to anchor their defense, keeping them in contention despite their roster upheaval.
Still, trading Simons isn’t without risk. His youth, scoring ability, and playmaking could make him a long-term fit alongside Boston’s core, especially if he continues to develop. Letting him go to save a few million might haunt the Celtics if he blossoms elsewhere while they’re left patching holes in a championship-caliber roster.
As the Celtics navigate this high-stakes chess game, the clock is ticking. Will they hold onto Simons and bet on his potential to keep their offense afloat? Or will they sacrifice the $100 million guard to escape the luxury tax “death blow” and rebuild around a new vision? One thing’s certain: Boston’s front office is in for a wild ride, and the NBA world is watching.