Though he had to wade through a feud with Kobe Bryant, he still built his legacy with the Los Angeles Lakers, earning three rings in a row from 2000 through 2002. His 1999-00 campaign (29.7 points, 13.6 rebounds, 3.8 assists and 3.0 blocks per game) in particular remains one of the greatest ever submitted by any player at any position.
But if O'Neal could do it over again, he'd keep wearing pinstripes—four titles be damned.
"Knowing what I know now, I would've stayed," the legendary center told the assembled masses at his Orlando Hall of Fame induction ceremony Friday, per Josh Robbins of the Orlando Sentinel. "I would've stayed and fulfilled my seven years and then looked at it differently after my seventh year."
As Mike Bianchi, a colleague of Robbins', explained, this ceremony is "an intensely bittersweet moment" for Orlando fans, who had to deal with him leaving. But for O'Neal, it's an opportunity for regret.
It's common knowledge that the big man's tenure with the Lake Show didn't exactly end on amicable terms. It was either him or Bryant in the end, and Los Angeles rolled with the younger shooting guard. But would he really have passed up on those chances to build his legacy in favor of the team that selected him out of LSU in 1992?
Given the emotion he showed while being honored, it's hard to say he wouldn't.
He also went on to clarify his reasons for wanting to make such a retroactive decision, via Robbins:
It was all business. Do I regret it? I never fully answered. I regret it sometimes. This is where I started, where I should've stayed. I actually wish that they [had] made it a law that whoever drafted you, you've got to stay there your whole career. No trades. No nothing. No free agency. No anything like that. Do I regret it? I regret it only because the DeVos family, they deserve a couple [of NBA titles]. …
I just wish I would've had more patience. It was all about I wanted to be protected from the bashing. What I mean by that [is] I wanted to win then. Even when I got there [to L.A.], I still got bashed and it still took four years to win. But I was very impatient. I was very young, and I thought that if I go there with those guys out there, that I could win right away. And that wasn't the case.
Of course, this all begs another question: Would the Magic have been able to win a title if O'Neal remained in place rather than fleeing in free agency?
That leads us down a rather deep rabbit hole, as one superstar staying leads to entirely different draft choices and a new direction. But if we assume that O'Neal's teammates largely remained the same, it's still likely that he could've gotten over the hump.
After all, O'Neal and the Magic had made it to the NBA Finals in 1995, eventually falling to Hakeem Olajuwon and the Houston Rockets. One year later, Michael Jordan was back in the league, and his Chicago Bulls took out Orlando before Shaq and Co. could make a repeat appearance on the sport's biggest stage.
The future could've been very different. Penny Hardaway would only keep growing, and the supporting cast wasn't exactly a shabby one—comprised of players like Nick Anderson, Horace Grant and Dennis Scott. Give that dynamic young duo of Hardaway and O'Neal a few more chances, and maybe they get the job done, especially if having a dominant center leads to Hardaway not feeling the need to push his physical limits.
If nothing else, the Magic would be an appealing destination for marquee free agents.
Any way you cut it, history would have been quite different.
Would Bryant have won rings for the Lakers and made his push toward his attempted status as a second Jordan? Would Wade have gotten to the free-throw line roughly 782 times in the 2006 NBA Finals and built his own legacy before LeBron James came to South Beach? Would we remember O'Neal as a top-20 talent in NBA history if he never got to adorn one of his fingers with jewelry?
On the flip side, would O'Neal have pushed closer to "Greatest of All Time" status if he'd remained in Orlando throughout his career and helped establish a Floridian dynasty?
We'll never know. But at least we're now aware that championships don't rule out regret.