Jordan's legend is a combination of raw talent, aggressive captivating persona, one of the best marketing and propaganda campaigns in capitalist history, and being at the right place at the right time.
Add in the fact that, often lost in the clutter, is the fact that Jordan is, at absolute worst and most denigrating, a top five player in NBA history.
The thing was, he is a hyper competitive monster, which is what sports fans tend to root for and cherish. That's why so many people hate on Barkley, Vince Carter, TMac, and other guys who never lived up to their potential, and why people hated on LeBron for not having "the will to win."
Once he retired, and his reign was thoroughly in the past, that was when people started to realize that yeah, Jordan won more games, but Charles Barkley would be way more fun to hang out with.