Shaquille O’Neal’s fearless days on the court may be behind him, but his bold moves in the media world show no signs of slowing down. It’s part of why he remains one of the most talked-about NBA personalities, despite having retired over 15 years ago. Case in point, on a recent episode of his podcast, Shaq openly inquired about the relationship status of a woman 25 years his senior.
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The NBA legend turned heads when he publicly shot his shot at 78-year-old media mogul Cathy Hughes during a conversation with comedian Rickey Smiley, who had worked with her. That was all the opening Shaq needed.
For context, Hughes is a trailblazer in the media industry. She’s the founder of Urban One (formerly Radio One), one of the largest African American–owned media companies in the United States.
Hughes’ impact is enormous—and clearly, she’s caught Shaq’s eye. With a net worth of over $450 million, she ranks as the second-richest Black woman in America, behind only Oprah Winfrey. This wasn’t one of Shaq’s usual playful shots—he was aiming for what might be the biggest shot of his life. And once he heard she was single, there was no holding him back.
He said, “Cathy Hughes so fine.” Shaq soon found out she was 78 years old, and he immediately took off his glasses. Then he made a face that’s hard to describe—but let’s just call it his way of shooting his shot at the media mogul. As the big fella tried his best to impress her from afar, both Smiley and Adam Lefkoe (also on the podcast) burst into laughter, unable to contain themselves.
“We can change that thing [the name of her company] to TV 1-34 and Radio 1-34. Once you go Shaq, you never go back, Miss Hughes,” the Lakers legend added.
While the moment had everyone in stitches, it wasn’t entirely out of character. Shaq is known for his playful flirting with celebrities on his podcast, usually in a lighthearted, comedic way.
Who could forget one of his most viral moments—flirting with Daily Pop guest host Rocsi five years ago? That clip had the internet buzzing for days.
That said, Shaq has been candid about his personal life. During an appearance on Angel Reese’s Unapologetically Angel podcast, he admitted he’s likely to stay single—and explained why.
He said, “I’m gonna end up alone…Because y’all be making rules up as you go along. There is no handbook on how to be the perfect man or perfect husband … and y’all be making sh*t up without telling us.”
Shaq has had his fair share of experiences with women, and while he claims he can’t understand women, the reason why he’d probably remain single isn’t limited to that.
During an appearance on Mo Talk Radio, Shaq said, “I had two perfect women, and I messed it up.” He was referring to Arnetta Yardbourgh, the mother of his first child, and his ex-wife, Shaunie Nelson. Shaq has openly taken responsibility for the failure of both relationships, admitting that the guilt still weighs heavily on him—and it’s what keeps him from committing to anyone else.
