Penny Hardaway has very few regrets about his basketball career, but one lingering disappointment revolves around Shaquille O’Neal. The missed opportunity to continue their partnership after Shaq joined the Lakers and teamed with Kobe Bryant left a void for both players. Hardaway has been open about his jealousy, especially seeing Bryant play alongside a dominant Shaq. Yet, contrary to what some might believe, this wasn’t the root of Hardaway’s rivalry with the Lakers legend.

Their rivalry dates back to their very first meeting, during Magic Johnson’s Mid-Summer Nights charity event. Speaking on the Out the Mud podcast, Penny shared, “Me and Kobe ended up getting into it during an All-Star game, like a Magic Johnson All-Star game. Kobe was one of those dudes where if you were the dude, he was gonna come at you, no matter what.”

At the time, Hardaway was a rising NBA star, known for his Memphis roots and fierce competitive edge. He wasn’t about to let the young Bryant challenge him without a fight. Hardaway elaborated, “And I got that Memphis in me, so as a young dude coming at me, I destroyed him and hit him in that game. He told everybody, ‘Wait for the season to start. I’ll kill his a**,’ right? I said, ‘Alright, bet.’ And that’s when we became rivals.”

Bryant, always confident in his abilities, didn’t back down. Their first regular-season showdown came in March 1997, with Hardaway getting the better of the rookie, outscoring him by 13 points. It was the beginning of an intense rivalry built on mutual respect and a shared drive to excel. While the Memphis spirit ignited the feud, Hardaway also holds one regret due to O’Neal.

Penny Hardaway weighs in on the fabled glory of gold

Penny Hardaway had a stellar career, but like many greats, he harbors one significant regret: not winning an NBA championship. For Hardaway, that unfulfilled dream is tied to his time with the Orlando Magic and his partnership with Shaquille O’Neal. Both players once envisioned leading the franchise to a title, but history had other plans.

Hardaway believes a championship was within reach had O’Neal stayed in Orlando. However, when Shaq made the move to join the Los Angeles Lakers, it left a void that was impossible to fill. Reflecting on this pivotal moment during the Let’s Be Clear Podcast, Hardaway shared, “I wanted to win a Championship. I felt like our Championship run was cut short when Shaq went from us to the Lakers. I knew that was going to be devastating. You lose a guy of that magnitude, but the only thing that I regret is not winning a championship.”

Adding to the sting was the way Hardaway learned about O’Neal’s decision, not through personal communication but via the media. The move not only dashed his championship hopes but also sparked a sense of jealousy, especially as he watched O’Neal dominate the league alongside Kobe Bryant.

“Watching him and Kobe together, for sure, there was some jealousy there because I felt like that should have been me and Shaq,” Hardaway admitted on The OG Point Forward. “It just didn’t happen, man. But I promise you, if we would have stayed together, it would have been a championship one.”

Though Hardaway never hoisted the Larry O’Brien trophy, his legacy as one of the most dynamic and versatile players of his era remains intact. Still, the what-ifs surrounding his partnership with O’Neal linger as one of the NBA’s great unanswered questions. What do you think about Penny Hardaway’s confession? Tell us in the comment section below!