Despite paying Off $300,000, Michael Jordan ‘Lawyered Up’ to Discourage Gambling Buddy’s $1,200,000 Demands

Jun 24, 2023; Nashville, Tennessee, USA; Team 23XI owner Michael Jordan looks on from pit road during qualifying before the Ally 400 at Nashville Superspeedway. Mandatory Credit: Christopher Hanewinckel-USA TODAY Sports

In the pantheon of sports legends, few names resonate as powerfully as Michael Jordan. Revered for his unmatched ability on the basketball court, the enigmatic superstar’s life has been in the spotlight for a long time. However, beyond the highlights and championships lies a lesser-known chapter—the intricate web of Jordan’s alleged gambling debts with Richard Esquinas, a San Diego businessman. Delving into one such financial entanglement, the Bulls legend even had to lawyer up on an occasion to protect himself from his own gambling friend’s demands.

 Esquinas made a claim for $1,200,000 to Michael Jordan, stemming from their high-stakes golf matches. Jordan, initially dismissive of the accusations, undertook a different course of action. He discreetly resolved a substantial portion—approximately $300,000—of the alleged debt, casting a shadow of uncertainty over the credibility of the claims. As the public spectacle escalated, Jordan found himself in a world of trouble, as per Slate.

Amidst the mounting turmoil, Jordan offered a rare glimpse into his psyche, characterizing his gambling habits as a manifestation of his relentless competitive spirit. For him, gambling was an extension of his unyielding determination to conquer any challenge. This revelation offered a peek beneath the surface of a sporting icon, revealing the intrinsic motivations that fueled his insatiable hunger for triumph.

Unmasking Esquinas’ Allegations: The Complex Reality

Enter Richard Esquinas, the figure at the center of the storm, asserting that Jordan owed a staggering $1.2 million in gambling losses. While MJ acknowledged the debt, he contested the astronomical figure. Esquinas’ narrative presented a long-winding tale, disclosing that the Bulls legend had indeed settled a significant portion—$300,000—of the debt before resorting to legal recourse. The reasoning behind Jordan’s decision to engage legal assistance remained shrouded in ambiguity, deepening the layers of intrigue surrounding the story.

The controversy took a sudden turn as Esquinas penned “Michael & Me: Our Gambling Addiction … My Cry for Help!” The tell-all book thrust readers into the world of high-stakes golf betting shared by Esquinas and Jordan. The publication provided an unfiltered glimpse into the dynamics of their relationship, shedding light on their shared exploits. This literary gambit rekindled public interest, propelling the story back into the forefront of conversations.

MJ was later clearly disappointed in the way he was presented in the book by someone he once considered a friend. He made his displeasure clear in an interview with Ahmed Rashad, where he made the following statement,

“I felt I was betrayed by this individual. He considered himself a friend. I don’t consider him a friend, because friends don’t do this to other friends.”

“I would be sick if I lost $1.2 million,” Jordan added. “And he would be sick if he reduced it to $300,000.” Jordan didn’t deny owing Esquinas $300,000, or paying him $200,000, but dismissed the $1.2 million figure as “preposterous” and overinflated. “He exaggerated to a point, and I’ve come up with my own conclusion to why he exaggerated … It sells books.”

To this day, it remains unclear what really happened between Michael Jordan and his former friend. However, no matter how preposterous the alleged debt sounds, Michael Jordan is also a competitor. So admittedly, anything is possible.

Michael Jordan loved gambling on the team plane too

During his time with the Chicago Bulls, Michael Jordan was a competitor to the highest level, whether he was on or off the court. His gambling came from this side of him, as the man would play Blackjack for hundreds and thousands of dollars a hand at the back of the plane. Meanwhile, there were some other teammates who never joined them, instead having their own games for just $1 a hand.

On one occasion, Jordan went to the front of the plane to play with them. When asked why he wanted to do it, here is what he said, as per Fadeaway World.

“So I can say I have your money in my pocket.”

Truly a different breed, the man wouldn’t even let the likes of Will Perdue and John Paxson keep their own $1 bills.