Michael Jordan’s Saddest Moment Involved a Wesley Snipes Movie

It’s tough to think that Michael Jordan could have a bad day. After all, Hir Airness won six NBA championships and cemented a legacy as the greatest player in the history of the sport. And with $2.1 billion to his name, it’s not like he’s hurting financially. But even societal elites experience despair just like the rest of us.

For a man who literally soared to new heights, he hit his lowest moment inside a dingy hotel room in Alabama while watching a Wesley Snipes movie. As it turns out, Michael Jordan’s baseball days in Birmingham were much darker and emotionally draining than we all believed.

Michael Jordan abruptly retired in his NBA prime

From the moment the Chicago Bulls drafted him with the third pick in the 1984 NBA draft, Jordan changed the NBA forever. The North Carolina native was truly a transcendent talent capable of dominating the game in a way previously unseen.

The 6-foot-6 shooting guard made the All-Star team in each of his first nine seasons. During that prolific stretch, Jordan led the league in scoring in every season from 1986-1992. Paired with fellow future Hall of Famer Scottie Pippen, the Bulls built a dynasty that not even Steph Curry and the Golden State Warriors could measure up to.

Famous for his competitive drive, Jordan elevated his game in the postseason. He rarely got a breather, but that didn’t matter. The five-time league MVP carried the Bulls to three consecutive NBA championships. It seemed like Chicago could conceivably spend the entire decade as the kings of the NBA. But out of nowhere, the reigning NBA Finals MVP took his talents from the court to the outfield in one of the strangest (and brief) retirements in sports history.

Bulls legend attempted to play baseball

Michael Jordan and baseball had a strange relationship. On one hand, it was mightily impressive that he could even attempt to make a major league team. On the other hand, it all felt a little suspicious. Why would the greatest player in the NBA give up his title to become the lowest guy on the totem pole in the minor leagues? Many speculated it related to his notorious gambling addiction. The NBA legend later said his father’s death inspired the decision. Maybe he truly loved the game, but either way, it ranks as one of the most bizarre decisions an athlete has ever made in his prime.

Jordan left the Bulls behind in favor of the Birmingham Barons. The Double-A affiliate of the Chicago White Sox couldn’t have represented a more dramatic life shift. His Airness went from playing in front of millions of television viewers to playing baseball in the middle of Alabama. The transition proved extremely difficult, as Jordan hit just .202 with 114 strikeouts in 1994.

The saddest day in Jordan’s life

That odd year toiling away in the desolate land known as minor league baseball proved to be an incredibly tough time in Jordan’s life. He went from being the alpha male to just another guy in the clubhouse. And spending his nights in dingy hotels definitely didn’t inspire many smiles from the NBA champion.

Jon Greenberg of The Athletic spoke with Melissa Isaacson, who covered the Bulls during their dynasty days. The accomplished writer actually traveled down to Birmingham to visit Michael Jordan. She needed little time to realize how emotionally drained Jordan looked:

I remember him being seemingly glad to see me like I was visiting him at overnight camp. It was muggy and rainy, the locker room was what you would expect in a Double-A clubhouse and I felt like taking him back with me to his old life where he belonged. Especially after he described his minor-league experience by telling me there were good days and bad days and days like one he had had recently when, he said, “I cried all day long.”

For a man who had just lost his father, Jordan relayed how a Wesley Snipes movie where his character’s father also died led to the saddest day of his life.

“The room was dark and I was laying on the bed and I guess it hit the right buttons because all of a sudden, I couldn’t stop crying,” he said. “I talked to my wife. I called everyone I knew. And I still couldn’t stop crying. I never had a day in my life that I felt that sad.”

Michael Jordan returned to the NBA and won three more titles before retiring for another three-year stretch. He finished his basketball career with the Washington Wizards before purchasing an ownership stake in the Charlotte Bobcats in 2006.