Jordan did have demons. In 1993, he admitted to suffering heavy losses from gambling, and became further disenchanted with basketball following the murder of his father that same year.
On the back of three straight titles, he retired that offseason, saying he no longer had passion for the sport. He didn’t stay out of the spotlight for long, however, making a surprise shift to minor-league baseball in 1994. (Spoiler: He wasn’t quite as good on a diamond.)
In 1995, he officially un-retired with a two-word statement: “I’m back.” The Bulls promptly went on to win another three straight titles, and Jordan kept padding his credentials as the greatest basketball player in history.
In early 1999, a month shy of his 36th birthday, he retired for a second time. Or so we thought.