In 2022, Shaquille O’Neal and Penny Hardaway sat side by side and recalled their rise and fall. It’s not an unheard story. Shaq and Penny were almost the Shaq & Kobe of the ’90s. Until O’Neal and the Orlando Magic had a bitter divorce to partner with Kobe Bryant. Over the years, Hardaway made his hard feelings public. While the former Orlando duo has ended that fallout, O’Neal is clinging to this friendship for a heartbreaking reason.

The Lakers legend got candid about his teammates on Dax Shepard’s Armchair Expert this week. Which meant we saw him get emotional over Kobe Bryant once more. (Yes, they’re calling him a ‘hater’ for his recent Kobe comments, but this isn’t about that.)

Two losses changed how Shaquille O’Neal looked at his relationships – his sister, Ayesha Harrison-Jex, in 2019, and Kobe Bryant in 2020. While Kobe’s was understandably abrupt, Ayesha battled cancer for three years. O’Neal admitted to Shepard that he wasn’t prepared for his sister’s passing, as family and doctors hid the severity of her diagnosis from him. So Shaq prioritized a business deal in LA while his sister passed away in Orlando.

“I never got to tell her I love her. But if I would have stayed there with her all day, maybe the doctor would have been like, ‘Hey, you have stage 4.’ Then I would have [said], ‘I love you. I love you. I love you. I love you.’,” Shaq said. TNT paid tribute to Ayesha in October 2019. Less than four months later, the entire NBA world is mourning the passing of Kobe Bryant and his daughter, Gianna, in a helicopter crash.

Regret once again hit Shaq for never properly ending his feud with Bryant. But the late Black Mamba remained close to the O’Neal kids and was present at Shaq’s youngest, Me’Arah’s game, a day before the crash. As the big guy put it, “Kobe was good to my kids. They love him. He’s Uncle Kobe… I always tell people this is dad’s beef.”

After losing Ayesha and Kobe, O’Neal practiced and preached his new mantra, “Hey man, reach out.” Two years after grieving, Shaq publicly showed an example of that.

Shaquille O’Neal has no regret about Penny Hardaway

After snagging Rookie of the Year in 1993, Shaquille O’Neal had the guns to tell the Orlando Magic to draft his Blue Chips co-star, or he would walk. That’s how Penny Hardaway arrived in Orlando. The team-up worked till 1996, and then it was Hardaway carrying the team. However, it was Shaq who was winning championships in the West with a new sidekick. Some reports then claimed that Shaq abandoned Penny for a $120 million.

It’s a good thing that O’Neal won’t hold on to this regret. “We are good,“ Shaq told Shepard about where he stands with Hardaway today. “It was just that we were, I was young and dumb…. Remember the ego thing?”

In recent years, Hardaway admitted he was jealous of Kobe Bryant. But in the 2022 HBO documentary, SHAQ, O’Neal and Hardaway both admitted egos came in the way. O’Neal talked about the breakdown of his partnership with Kobe in this series, too. Today, he tells Dax Shepard that the heart-to-heart with Penny also left him heavy.

There have been many public moments of Shaq and Penny back to their old camaraderie. A poignant moment in their friendship was when Hardaway came on The Big Podcast, where O’Neal made an emotional apology for leaving. If, perhaps, Orlando had taken a different decision 30 years ago, Shaq and Penny believe they are the championship-winning duo that never was.