Michael Jordan is far from the first celebrity to struggle with gambling, but his habits are somewhat infamous. Take, for example, the time the ex-NBA player went on a 36-hour gambling spree, according to Sportscasting. In March 2021, fellow basketball star Antoine Walker appeared on an episode of "All Things Covered" to recount how he and Jordan were down nearly $1 million during a seemingly endless game of spades. At some point, Jordan nearly fell asleep at the table. "[Jordan] got too tired," Walker said. "We couldn't go no more." However, that story pales in comparison to the time that Jordan lost an alleged $1.25 million during a 10-day golfing binge.
San Diego businessman Richard Esquinas wrote a whole book about his gambling problem with Jordan in 1993, aptly titled "Michael & Me: Our Gambling Addiction ... My Cry For Help!" Esquinas believed he "was a controlled gambler" until he and Jordan "went berserk" and racked up more than $1 million in debt over a 10-day golf bender, according to The Washington Post. However, Esquinas claimed that Jordan had allegedly negotiated to have the debt reduced to $300,000. In the wake of the claims, Jordan's agent declined to verify Esquinas' story, and Nike — who sponsored Jordan at the time — criticized Esquinas. "It's so out of proportion here," the company's public relations manager said, per The Washington Post. "[Jordan] is ... being attacked by people who are using him to get publicity."
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