Bill Simmons labels ex-Philadelphia ace the NBA’s biggest disappointment in 25 years

Photo by Amy Sussman/Getty Images the New Yorker

Bill Simmons labels ex-Philadelphia ace the NBA’s biggest disappointment in 25 years

Originally posted on HITC | By Luca Rosano | Last updated Nov 27, 2025 9:17 AM ET

The Philadelphia 76ers suffered their heaviest defeat of the season, falling badly to the Orlando Magic.

Even without Joel Embiid and Paul George, the Sixers have usually managed to keep things competitive this season.

But Tyrese Maxey could not pull them through this time, and the loss really highlighted some deeper issues within the team.

Over the years, disappointment has been a recurring theme for the 76ers. Their history is marked by a long list of letdowns, from playoff runs that ended too soon to players who failed to meet expectations.

Bill Simmons names Ben Simmons as the NBA’s biggest disappointment of the last 25 years

Photo by Ezra Shaw/Getty Images

One of the more frustrating storylines in 76ers history is that Ben Simmons never became the player many expected him to be.

Early on, he was praised for his combination of size and skill, with some even suggesting he could take over from LeBron James as the face of the league.

Simmons got off to a promising start in Philadelphia, winning Rookie of the Year and earning three straight All-Star selections. He also made back-to-back All-Defensive teams.

But then things fell apart. After leaving Philadelphia, his confidence never returned, and since being traded to Brooklyn, he has struggled to find a consistent role.

Consequently, Ben Simmons was labelled by Bill Simmons as the NBA’s most disappointing player of the past 25 years.

“I think my number one most disappointing guy the last 25 years is Ben Simmons.

“I think he was there for like a year and a half, when it was like, I see the vision of what Ben Simmons [is], I think he can be the one of the 10 best guys in the league. It’s right there.

“You kind of look like LeBron sometimes when you have a head of steam downhill, and defensively you might be one of the three best guys in the league, and you are a foundation block of a team that could maybe win a title.

“And then it just, that Atlanta series, it went sideways and I’m disappointed by it,” the podcaster stated.

Ben Simmons is still looking for his next opportunity

Last season, Simmons was with the Los Angeles Clippers, but he has not landed a new team since then.

Back in September, just before the season kicked off, his agent Bernie Lee cut ties with him.

Reports suggested it was because Simmons turned down an offer from the New York Knicks, which was his only one of the offseason.

Soon after, a fan asked him on Instagram if he had retired. Simmons replied simply: “no”.

With OG Anunoby missing time due to a hamstring injury that will be re-evaluated when they return home, there is a chance New York might look back in his direction.

This article first appeared on HITC and was syndicated with permission.

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