“They need to change the rule that whoever drafts you, you gotta stay with them your whole career” – Shaq admitted he regrets leaving Orlando originally appeared on Basketball Network.
In one way or another, every NBA player lives with regret: regret for the college they chose, regret for the relationships they fractured, regret for the teams they signed with and regret for the sacrifices they didn’t make.
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Shaquille O’Neal has been open about the many regrets that have tormented him since his retirement. He wore his heart on his sleeve during his career, but his ego often got in the way, preventing him from sometimes achieving his full potential or the upside he had with teammates.
One of those instances was his tenure with the Orlando Magic, which, according to O’Neal, happened to be the best years of his life.
Shaq’s regret
To his credit, instead of running away from all the contentious decisions throughout his career or choosing not to discuss them, O’Neal has been as candid as you can be after his playing career has concluded. It doesn’t matter if it’s a podcast appearance or him speaking his mind on National television; the four-time champion is never shy about broadcasting to the world the many mistakes he made along the way.
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Coming into the Association, O’Neal was one of the most highly touted prospects in league history, and the Magic selected him with the first overall pick in 1992. It was a no-brainer, especially since the organization was craving a franchise cornerstone who could take them to the next level.
Needless to say, Shaq didn’t disappoint, and put together one of the greatest rookie campaigns ever by averaging 23.4 points, 14.0 rebounds and 3.5 blocks per game. It was rare to see that level of dominance from a teenager, and it earned him All-Star honors in his first season, becoming the first player since Michael Jordan in 1985 to do so.
O’Neal’s ascension would continue over the next few years, firmly establishing himself as one of the greatest players in the world. The individual accolades came pouring in, and he powered the Magic to their first Finals appearance in franchise history in 1995.
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It was all sunshine and rainbows in Florida until the team prioritized running partner Penny Hardaway’s contract over his own in the summer of 1996, bruising O’Neal’s ego and causing him to want out.
In the years that followed, the legendary big man confirmed that his decision may have been emotionally driven instead of logically sound, and he still regrets not continuing in Orlando after a successful first four years.
“I hate the business of basketball,” O’Neal said. “They need to change the rule that whoever drafts you, you gotta stay with them your whole career. My first four years there were probably the best years of my life.”
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A different legacy?
O’Neal will always have a special place in his heart for the Magic, and it’s safe to say that affinity grew even stronger when he became the first player in franchise history to have their jersey retired last year.
But even with his admirable sentiment towards the organization and his hope that he had stayed there longer, it’s safe to say that if O’Neal had remained in Orlando for the entirety of his career, his career and, subsequently, his legacy would have transpired far differently.
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For one, there’s a chance that Shaq would have never won a championship. He and Hardaway made the Magic a contender, but since their tenure, the franchise has had only one other occasion in which it made the Finals. Additionally, O’Neal would likely never put together a three-peat as he did with the Los Angeles Lakers between 2000 and 2002. During that stretch, the seven-footer collected three consecutive Finals MVPs, and to this day, those three seasons are considered perhaps the most dominant in league history.
If Shaq didn’t take his talents to Los Angeles, it’s hard to imagine the Magic front office continually surrounding him with enough talent to compete for titles year after year like the Lakers did. Hardaway was constantly hurt not long after their split, and it’s safe to say O’Neal would have never had another teammate as talented as Kobe Bryant while donning an Orlando jersey.
Without the rings, Shaq’s ranking among the all-time greats would undoubtedly be impacted, too. Currently, he is universally locked as a top-10 player of all time, but that changes without the championship success. In an alternate universe, would he be remembered as a dominant force that could never get over the hump? Or a player who was too loyal to a franchise that never built the right team around him?
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When legacies are on the line, it’s a completely different conversation. Yes, it’s nice for O’Neal to say the Magic years were the best in his life and he wished a rule existed that you remained with the franchise that drafted you throughout your entire career, but he’s clearly never undergone the mental exercise of projecting the consequential impacts on his legacy.
This story was originally reported by Basketball Network on Aug 14, 2025, where it first appeared.