While Shaquille O'Neal and Michael Jordan had plenty of intense battles, they were never able to face off in the postseason on a level playing field. O'Neal's Orlando Magic defeated Jordan's Bulls in 1995, but Jordan only came out of retirement in the middle of the season. When Jordan was winning his final two championships, O'Neal was waiting for a teenaged-Kobe Bryant to develop enough to get him back to the NBA Finals. The two never duked it out under ideal circumstances with the right teammates.
But if they had? O'Neal is betting on himself. When asked on SportsCenter if his three-peat Lakers from 2000-02 could defeat the Bulls at their peak, he didn't hesitate. "Of course," O'Neal said. "Yes. Easily."
What makes Shaq so confident in this outcome? "I would have killed Luc Longley, Bill Wennington, Cartwright, yea." The Bulls were hardly known for their size. Two-time Defensive Player of the Year Dennis Rodman might have made a difference, but O'Neal eviscerated a four-time winner of that award in Dikembe Mutombo when the Lakers defeated the Philadephia 76ers in the 2001 NBA Finals.
If one thing were to slow down the Lakers, in O'Neal's mind, it would be his free-throw shooting. With Phil Jackson coaching the Bulls, Shaq is almost certain they would have gone to the now-largely defunct hack-a-Shaq strategy of sending him to the line every possession. O'Neal shot 52.7 percent from the free-throw line during his career. A long enough stretch of misses could swing a game, which could swing a series.
Jordan's Bulls never faced a duo nearly as accomplished as O'Neal and Bryant, though it could be argued that their three championships were a result of the power vacuum Jordan left behind by retiring. Their lack of size would be problematic in such a matchup if Rodman (or Cartwright depending on which version of the team is in this series) could hold his own against Shaq at his apex. It's a series we unfortunately never got to see. The 1995-96 Bulls posted the greatest non-Warriors regular-season record of all time at 72-10. The 2000-01 Lakers posted the greatest non-Warriors postseason record of all time at 15-1. If nothing else, this would have been one of the greatest series in NBA history.