The same question but two different friends are the cause of Shaq’s lingering regret. Once again he wondered aloud how many rings he could’ve won had he stayed with Kobe or with Penny. But while Penny Hardaway, Shaquille O’Neal’s ‘Kobe before Kobe,’ was on The Big Podcast, the latter regret was stronger. Far from his hotheaded playing days, O’Neal has the benefit of hindsight to admit he let ego break up two of his best on-court partnerships. We know how he left the Lakers to Bryant. But leaving Orlando to Penny was a whole other story.

It was Shaq’s first team and he quickly emerged as Orlando’s Superman. He had the pull to make the Orlando Magic draft Penny Hardaway a year into his NBA career. The duo was the reason Magic was the last team to ever beat the Michael Jordan-led Bulls in a playoff. They made it to the 1995 Finals and lost. That’s when things fell apart.

Shaq’s contract was up after the finals. Famously, he wanted to beat his rival Alonzo Mourning’s $100 million contract that year. But Orlando wouldn’t give it to him. As Shaq recounted to Adam Lefkoe, they didn’t let him down easy. “When they said it wasn’t my team no more, it hurt a little bit. So since they said it wasn’t my team, it’s his [Hardaway] team now, let’s see what the other teams going to offer me. So the other teams offer me more than what my team was willing to offer and I took advantage of it.”

As O’Neal’s then-agent Leonard Armato told Essential Sports, The Lakers upped their offer from $95 million to $120 million, also getting draft picks in the bargain through which Jerry West got Kobe Bryant in 1996. Shaq took the offer because he knew he was worth it and he’d go on to win three consecutive titles with Bryant before they’d part on bitter terms too.

Shaq told Lefkoe, his departure from Orlando and LA were the few times he let his “professional jealousy” come in the way. In Orlando, he was bothered that Penny was also more popular, evident from his jersey sales beating Shaq’s. So when it wasn’t ‘Shaq’s team’ anymore, he left.

Magic’s Shaq has grown up

The what-ifs regarding Penny and Kobe still bother Shaq and he blames it all on his ego. He’s glad he’s outgrown that, but he regrets what happened in the ’90s. He said he selflessly urged Penny to get a better extension from Orlando. ““I stuck up for him. When I signed and was sitting out out maybe he was sticking up for me,” Shaq said.

As history went, Shaq left for the West. Three decades later, he says he’s no longer that egoistic and hungry for titles and approval. It’s a lesson Penny could also share in as he too admitted he was jealous of what Shaq and Kobe formed.

Not to dig up old wounds for Shaq but how many titles you think he and Penny could’ve won.

Stay tuned for more such updates, and to follow what Shaq’s ex-agent, Leonard Armato, has to say about the infamous Shaq-Kobe feud, Caitlin Clark’s Olympic snub, and more, watch this video.