“I made a lot of d—— mistakes to where I lost my family and didn’t have anyone. I was an idiot… I lost my whole family. I’m in a 100,000-square-foot house by myself.” It’s a rare thing to hear a giant sound so small. But that’s Shaquille O’Neal, the larger-than-life Hall of Famer, getting brutally honest about the one loss that still haunts him—not on the court, but at home. For a long time, Shaq was seen as the guy who had it all: four championships, blockbuster movie roles, a platinum rap album, and what looked like the perfect family. But in a recent, raw conversation with Mike Tyson on “The Big Podcast with Shaq,” the NBA legend pulled back the curtain on the painful aftermath of his divorce from Shaunie Henderson.

For years, their marriage seemed like a rock in the chaotic world of pro sports. They married in 2002 and built a family of six children, but Shaunie later wrote that she saw the marriage “beginning to crumble” long before the public knew. She described a husband struggling to be a “world-famous, thirty-something multimillionaire… and a father at the same time.” The breaking point came in 2009 when, visiting Shaq in Cleveland, a housekeeper told her, “The missus will be back soon.” It was a devastating moment that made her feel like a stranger in her own life, and the divorce was filed soon after.

While the divorce was years ago, the regret is still fresh for Shaq. And now, as a father, he’s trying to turn that pain into a lesson for his children. But as he revealed in his conversation with Mike Tyson, that’s easier said than done. “When I separated from my family for living my foolishness—especially the boys—I had to open up to the boys and say, ‘Hey, this is who I am, this is what I did. Never want you to be like me. Want you to learn from my mistakes.’,” Shaq explained.

But Tyson, a man who knows a thing or two about life’s hard lessons, quickly interjected with a dose of reality. “But it doesn’t work like that,” he said. “They don’t learn—they gotta touch the fire to know it’s hot.” It was a moment of profound, and perhaps painful, truth. Shaq admitted it was a “good point,” but it highlighted the central struggle of his post-career life: how do you protect your children from the same mistakes that cost you so much?

Shaquille O’Neal explained that he’s tried to be an open book with his kids as they’ve gotten older. “When they got—like right now, [my son is] 22—I talk to him like he’s not even my son. So when they got older, I opened up the books and said, ‘Hey, this is the foolishness that I did. This is how I lost the family. These are things you should never do.'” He said he learned that approach from his own father, who always told him, “I don’t want you to be like me. I want you to be better than me.”

But again, Tyson offered a different, more sobering perspective. “Well, Shaq, can I be honest with you? From my experience in life—they’ll probably make more money and they’ll probably be more successful, but they’ll never be better. That’s just how it is.”

It’s a heavy thought, but it gets to the heart of Shaq’s parenting philosophy. He’s famously tough on his kids when it comes to money. “In order to get my cheese, you have to present me with two degrees,” he once said. He clearly wants to give his children the one thing he couldn’t give himself: a life without the same mistakes. But as Mike Tyson reminded him, some lessons can only be learned in the fire.

But long before the rings, the movies, and the empty mansion, there was just a kid with a ridiculously big dream.

Shaquille O’Neal’s rise to riches and dominance

Inspired by Magic Johnson’s game-changing $25 million contract, a young Shaq had a simple goal. “When I was coming out of high school, I wanted to make $8 million for 10 years,” he said on the Off the Record podcast. But when you’re a 7’1″ force of nature, your dreams tend to get bigger. After being drafted No. 1 overall, his agent came to him with a new number: $70 million. Shaq’s reaction? “I was like, ‘What did you say to me?’”

He ended up with a seven-year, $40 million deal with the Orlando Magic—a number that looks like a bargain today. But by 1996, the game had changed. His agent’s new prediction? “You’re gonna be the first $100 million player.” While a couple of other guys beat him to it, the Lakers came calling with a deal that would change his life, and the league, forever.

The story of how it went down is pure Shaq. He was at a strip club during the 1996 Olympics when his agent called. “I get to the hotel, Jerry West is in a Versace pimp coat, he said, ‘Man, I got some good news for you’,” Shaquille O’Neal remembered. West slid a piece of paper across the table. “All I saw were zeroes,” Shaq said. “I was like, ‘What is this?’ He’s like, ‘120 for seven, and after four you can renegotiate again’. So now I’m already pre-thinking, ‘S—, if I’m getting 120 now, next one I’m gonna get 180’.”

But West was selling more than just money. He was selling a vision. He told Shaq about a high school kid he’d just traded for, a kid from Charlotte. “I just signed this kid out of Charlotte. Pshhh… you and him…” That kid, of course, was Kobe Bryant. The rest is history.

It was a partnership that would bring three championships to Los Angeles and define an era of basketball. But looking back, it’s the story of two different Shaqs. There was the young guy who chased and conquered every professional goal. And then there’s the older, wiser man, having lost the one thing that money and fame couldn’t buy back: his family. It’s that painful human journey that truly defines his legacy.