10 Biggest "What If?" Questions In NBA History

This one has been explored for nearly two decades, including in an excellent ESPN 30 for 30 documentary, This Magic Moment, but it's no less fascinating to think about: had Shaquille O'Neal not left the Orlando Magic in 1996, could he and Penny Hardaway have won a championship together, as they had come so close to doing in 1995?

The Shaq and Penny-led Orlando Magic famously suffered a humiliating sweep at the hands of Hakeem Olajuwon and the Houston Rockets in the 1995 NBA Finals. The next season, they were ejected from the playoffs by the almighty '96 Chicago Bulls. However, despite those losses, they were still young and were playing at an astonishingly high level. Had they grown together, Shaq would have developed into the bruising monster he became in Los Angeles and the extra help would have allowed Penny to better preserve his body. Add in some team building by the front office and the Magic definitely could have snagged a ring or two in the post-Jordan era of 1998 and beyond.

Although Shaq went on to achieve great success in Los Angeles, it's hard not to think he left something truly special on the table in Orlando.