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Should the Celtics consider trading Jaylen Brown for Ben Simmons?

How desperate are the Celtics for a roster shake-up?

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Boston Celtics v Philadelphia 76ers Photo by Drew Hallowell/Getty Images

There’s something off about this team and it is hard to put a finger on exactly what it is. The fanbase grumblings are rumbling to a roar after a three-game losing streak and many are calling for a major shake up.

Jayson Tatum still appears to be the likely face of the franchise, so perhaps the biggest shake up that could be done is dealing Jaylen Brown. I’m not personally in favor of that, but this is a discussion that has to be had at this point.

Taking this another logical end, the most available star on the market is Ben Simmons (and all his baggage). John Hollinger suggests that the Sixers call up the Celtics in his latest column for The Athletic.

While the Sixers still hold out hope for Damian Lillard or Bradley Beal, those options remain unlikely. 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…)

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. 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.

The U-turn on most Philly trade scenarios is that in a Brown deal, the Sixers are likely the ones who would need to cough up players and/or picks. Brown is still signed for two more years at reasonable money and made the All-Star team last season.

There’s a lot to unpack here, but I’ll start with this. Just the fact that this is a discussion point is a big loss for the Celtics. Before the season, I’d have laughed off an idea like this in a heartbeat. Now it isn’t so easy to brush off.

I agree with Hollinger that picks and/or players would need to be coming back to Boston. Complicated three team deals could certainly be in play. Brad Stevens has been bold and unafraid of making moves, so maybe he’ll get creative.

What about the fit? In this scenario, we’d still have Marcus Smart on the team. Simmons certainly doesn’t help our shooting and spacing issues, but he is a connector player, meaning he moves the ball effectively, which is something this team desperately needs. He’s also a Defensive Player of the Year candidate who would further cement this team’s identity as a defense-first focus. Ime Udoka even has history working with him.

In an overhaul like this, Brad might even consider moving Horford, Schroder, and perhaps even Smart in separate deals.

So the question is, just how much of a shakeup are you willing to advocate for? How crazy do you want to get?