‘It just went sideways’: Australian Ben Simmons rated the most disappointing NBA player of the 21st century
Australian basketball star Ben Simmons has been named the most disappointing NBA player of the 21st century.
Prominent analyst and historian Bill Simmons, speaking on his podcast, viewed the Aussie as the clear choice above all other candidates.
Selected by Philadelphia with the No.1 pick in the 2016 draft, Simmons won rookie of the year in his first season in 2018 and would go on to make three straight All-Star rosters, make an All-NBA third team and two All-Defence teams, between 2019 and 2021.
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One of the best defenders in the league, the Victorian was also a powerful scorer and passer in transition given he was effectively a 209cm point guard.
Ben Simmons of the Los Angeles Clippers in 2025. Getty
Simmons drew comparisons to LeBron James for his size, skill and athleticism and looked on his way to becoming one of the game’s biggest stars, even signing a max contract with Philadelphia worth $241m.
His only issue was his complete reluctance to shoot from three point range, something that developed into a clear stigma during his time the with the 76ers, ultimately leading to free throw shooting yips as well.
In the 2021 playoffs, he famously passed up a wide open shot under the ring as the 76ers melted down as huge favourites against the Atlanta Hawks in the second round, likely fearing the potential of being fouled and needing to shoot more free throws.
Things spiralled from there.
He was blamed by coach Doc Rivers and star teammate Joel Embiid for the loss to the Hawks, with the awkward decision not to shoot highlighted by both.
Simmons would refuse to play for the 76ers the next season, holding out despite having four years to run on his max contract. Things only became more and more awkward, and he was eventually traded to Brooklyn for James Harden.
However, his career was never the same. Back injuries and a lack of confidence turned an All-NBA level point-forward into a back-up centre, and things fizzled out from there with the Nets, before playing a role for the Clippers in 2025 on a minimum contract.
The 29-year-old has not signed with a team for the 2025-2026 season, despite confirming via Instagram that he has not retired.
Ben Simmons during his time with the Brooklyn Nets. NBAE via Getty Images
Bill Simmons, while discussing Memphis Grizzlies guard Ja Morant and his own issues across the last few seasons, unpacked his disappointment with the Aussie.
“It’s been 25 years of the 21st century, I was thinking back a little bit to everything we’ve seen and I was thinking about Ja Morant who I just have have been so disappointed by for so many different reasons the last couple years,” he said on his self-named podcast.
“I was wondering. Has he thrown his hat in the ring for one of the most disappointing stars of the past 25 years?
“And what are the qualifications? Jay Williams hurt his leg in a motorcycle accident, that doesn’t count. Greg Oden I can’t be disappointed by.
“I made a list of the guys I was most disappointed by … I think my number one most disappointing guy of the last 25 years is Ben Simmons. Because I think he was there for like a year and a half.
“It was like I see the vision of Ben Simmons, I think he can be 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 in that Atlanta series, it just went sideways and I’m disappointed by it.
“He was third team All-NBA.”
Ben Simmons and Doc Rivers. Getty
It remains unclear if Simmons even wants to sign with an NBA team this season, rejecting pre-season interest and firing his agent. Simmons is the highest earning Australian basketballer in history at $305m.
The New York Knicks have been strongly linked with him at stages, but nothing has developed yet.
He never represented the Boomers, pulling out of every Olympic and World Cup pursuit, usually at the last minute.
Others mentioned by Bill Simmons among the most disappointing players since 2000 included Pelicans forward Zion Williamson, Serbian basketballer Darko Miličić, point guard Steve Francis, Timberwolves forward Derrick Williams, Sacrmanento guard Jimmer Fredette and floated the possibility of Lakers championship centre Anthony Davis making the list for not living up to his full potential.
