What an interesting thought! What if… what if Shaq had stayed in Orlando with the Magic for his entire career? Talking with The Basketball Network recently, the big man said something very interesting: “They need to change the rule that whoever drafts you, you gotta stay with them your whole career.” Wow… really?
Every NBA player carries a few “what ifs.” Maybe it’s a college choice they’d take back, a contract they wish they’d signed, or a teammate relationship they let sour. For Shaquille O’Neal, one of his biggest regrets is crystal clear — leaving the Orlando Magic.
Shaq has never been shy about admitting the mistakes he made along the way. Whether on a podcast, in an interview, or live on TV, he’s the first to say his ego sometimes got in the way. And when it comes to his time in Orlando, he calls those years “the best of my life.”
The Magic Years
When Shaq entered the league in 1992, he was one of the most hyped prospects in NBA history. The Magic had the first overall pick, and it was an easy call — they wanted a franchise cornerstone, and Shaq was it.
He didn’t disappoint. As a rookie, the 7-foot-1 phenom averaged 23.4 points, 14 rebounds, and 3.5 blocks per game. He was so dominant, so fast, that he became the first rookie since Michael Jordan to make the All-Star Game.
Shaq’s rise only continued. By 1995, he had powered the Magic to their first NBA Finals appearance. Orlando was on the map, and Shaq was a superstar.
But in 1996, contract negotiations got messy. The team focused on locking up Penny Hardaway before Shaq, and the big man felt slighted. Hurt feelings led to a big decision — leaving Orlando for Los Angeles. Looking back, Shaq admits it may have been more of an emotional move than a smart business one.
“I hate the business of basketball,” he’s said. “My first four years [in Orlando] were probably the best years of my life.”
What Could Have Been
Shaq will always have love for the Magic — and that bond grew even stronger last year when the team retired his jersey, the first player in franchise history to receive the honor. Still, he can’t help but wonder how things might have been if he’d stayed.
On one hand, the Magic were contenders with him and Penny. But would they have won titles? Shaq’s three championships with the Lakers — and three straight Finals MVPs from 2000 to 2002 — were built on a partnership with Kobe Bryant, one of the greatest duos in NBA history. In Orlando, Penny’s injuries piled up, and it’s unlikely Shaq would have had that same kind of co-star.
Without those rings, Shaq’s place in basketball history might look very different. He’s now universally ranked among the top 10 players of all time, but without championship success, would people remember him as the dominant big man who never got over the hump?
It’s fun to imagine the alternate reality — Shaq as a lifelong Magic player, towering over downtown Orlando as the city’s permanent basketball king. But even he knows the business decisions, the moves, and yes, the regrets, all shaped the legend we know today.