Time For Celtics To Actually Consider Jaylen Brown-Ben Simmons Trade?

The Celtics, by all accounts, hung up on the 76ers last month — figuratively, if not literally — when Philadelphia reportedly reached out about trading Ben Simmons to Boston for Jaylen Brown.

Well, maybe the Sixers should call back.

Because while there’s a strong argument to be made against such a deal, from Boston’s perspective, the Celtics have spent a lot of time lately licking their wounds. And those struggles aren’t completely connected to the COVID-19 outbreak that has made life even more difficult for the C’s.

There’s now a large enough sample size to suggest something needs to change for Boston to take the next step. The Celtics, who dropped to 16-19 with Wednesday night’s ugly loss to the Los Angeles Clippers at TD Garden, finished 36-36 last season. They’ve done nothing but regress for north of 100 games, a stretch in which they hired a new head coach, Ime Udoka, and replaced Danny Ainge with Brad Stevens as president of basketball operations.

Trading Brown to the Sixers in a blockbuster for Simmons might not cure all that ails the Celtics. Boston’s best course of action, albeit frustratingly tedious, might be to remain patient in the hopes of eventually adding a third star alongside Brown and Jayson Tatum.

But the Celtics’ mounting woes are such that it’s fair to start thinking, if not acting, boldly. And NBA analyst John Hollinger took that step Thursday for The Athletic in assessing seven players — including Simmons — who will dictate much of what happens before the trade deadline.

“While the Sixers still hold out hope for Damian Lillard or Bradley Beal, those options remain unlikely,” Hollinger wrote of a potential Simmons trade. “What are the realistic alternatives? The most prominent one is if Boston would consider shaking things up with a Simmons-Jaylen Brown deal. This would likely be a non-starter in Beantown were it not for the Celtics’ bizarre torpor of the past two seasons, but it’s getting to the point of ‘they might need to look at this.’ (As for reuniting Simmons and Al Horford? Ehhh…)”

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Look, Simmons is a problem in Philadelphia. That alone should give any team pause about relinquishing valuable assets and absorbing his hefty contract. Who’s to say swapping Brown for Simmons wouldn’t just create even more of a headache, with minimal on-court improvement to show for it?

The Brown-Tatum tandem simply hasn’t worked to this point in their respective Celtics careers, however. And maybe it never will. Simmons’ skill set, if nothing else, is less redundant alongside Tatum, who’s competing with Brown for shots on the wing as the Celtics lack a true point guard and front-court depth.

“Simmons would give Boston a real point guard and let Jayson Tatum take all the shots; Simmons might compromise spacing in lineups with Robert Williams, but the Celtics’ defense with Williams, Simmons and Marcus Smart could be ridiculous,” Hollinger wrote. “From Philly’s end, obviously, having an All-Star-caliber wing would be a big upgrade, although it still needs a plus passer or two.”

All in all, the negatives of trading Brown for Simmons outweigh the positives. So, it’s probably unlikely we’ll see the Celtics and 76ers swap All-Stars in the coming weeks, no matter how far Boston plummets down the Eastern Conference standings.

The conversation is far more fascinating now than it was at the beginning of the 2021-22 NBA season, though. Maybe to the point where Sixers president of basketball operations Daryl Morey can call the Celtics without immediately being greeted with a dial tone.