Juanita Vanoy and Michael Jordan's Divorce Cost Him $168 Million — inside Their Split

Michael Jordan isn't just the biggest icon in basketball history; he also paid out the biggest divorce settlement.

In 2006, NBA icon Michael Jordan forked out the biggest divorce settlement in sporting history, handing over a stupendous $168 million to ex-wife Juanita Vanoy.

The couple had been married for 17 years and shared two sons, Jeffrey and Marcus, and a daughter, Jasmine. The couple's relationship had been rocky due to the NBA star's infidelities, but they had always reconciled.

Just 3 months after his wedding to Juanita, Jordan started a torrid affair with a woman named Karla Knafel

Michael Jordan and Juanita Vanoy at the New York City Essence Awards 2000 | Source: Getty Images

Michael Jordan and Juanita Vanoy at the New York City Essence Awards 2000 | Source: Getty Images

THE FINAL STRAW

The marriage of NBA's biggest star had been dragging through successive allegations of infidelities, and Jordan's involvement in his career which kept him distant from his growing family.

The final straw that drove Juanita to file for a divorce was a blackmail attempt by a woman Jordan had had an affair with, just 3 months into their marriage.

 NBA legend Michael Jordan and his mother Deloris Jordan in 1988 | Source: Getty Images

NBA legend Michael Jordan and his mother Deloris Jordan in 1988 | Source: Getty Images

MEETING JUANITA

When Jordan met Juanita he was already an NBA rising star, constantly harrassed by female fans. His mother, fearful that Jordan would be swept up in a licentious lifestyle, chaperoned him everywhere he went.

 Michael Jordan #23 of the Chicago Bulls plays against the Philadelphia 76ers in 1996 | Source: Getty Images

Michael Jordan #23 of the Chicago Bulls plays against the Philadelphia 76ers in 1996 | Source: Getty Images

The 20-year-old player met Juanita Vanoy and was struck by her cool maturity. Juanita was 24, and she didn't seem impressed by Jordan's superstar status. They started dating, and with his family's approval, they became engaged.

UNEXPECTED PREGNANCY

In early 1988, Juanita discovered that she was pregnant. Even though they were engaged, Jordan's reaction was negative. He just didn't feel ready to become a father.

To protect herself and her unborn child, Juanita instructed her lawyers to draw up a settlement agreement whereby Jordan would take care of their financial needs. Months of complex negotiations over the terms ensued between the two legal teams.

GETTING MARRIED

Then one day Juanita called her lawyers and instructed them to start working on a prenup -- she and Jordan had decided to get married before their baby was born. 

LAS VEGAS WEDDING

But the prenup was never signed because Jordan and Juanita flew to Las Vegas with some friends and ended up getting married in an all-night chapel at 3:30 in the morning.

PRENUP TO POSTNUP

Juanita's lawyers got one more surprise call, advising them that the couple had married without a prenup in place and that they should now draft a postnuptial agreement.

WELCOMING THEIR FIRST CHILD

The wedding was in September, and on November 18, 1988, the Jordans welcomed their first child, a son, named Marcus. But fatherhood didn't help Jordan settle down.

FIRST INFIDELITY

Just 3 months after his wedding to Juanita, Jordan started a torrid affair with a woman named Karla Knafel, an affair that was to last 3 years, and cost him $250,000 to get out of.

From then on, the man who was a soaring angel on the basketball court started slipping into a life of licentiousness and vice. Behind the scenes, the devoted father was a habitual philanderer and a gambling addict.

 Michael Jordan and wife Juanita at the world premier of "Michael Jordan To The Max" in 2000 in Chicago | Source: Getty Images

Michael Jordan and wife Juanita at the world premier of "Michael Jordan To The Max" in 2000 in Chicago | Source: Getty Images

HOLDING IT TOGETHER

Despite it all, Juanita, now the mother of three children, Jeffrey, Marcus, and Jasmine, didn't give up on her marriage. In fact, many of Jordan's colleagues cite Juanita as the stabilizing influence that helped the NBA icon reach his full potential.

FALLING APART

By 2002, Juanita, who kept out of the limelight as much as she could, had had enough. She hired a private investigator who registered the player as seeing over 7 different women in just one week.

Juanita filed for a divorce citing irreconcilable differences, but Jordan talked her around, and she agreed to give their marriage another chance. However, their reconciliation was shortlived.

Juanita Vanoy attends the Simone I. Smith Trunk Show at Neiman Marcus Atlanta in 2012 | Source: Getty Images

Juanita Vanoy attends the Simone I. Smith Trunk Show at Neiman Marcus Atlanta in 2012 | Source: Getty Images

HAUNTED BY THE PAST

Karla Knafel was back, and she wanted $5 million from Jordan and claimed she had given birth to his child. The case went to trial, and the judge dismissed Knafel's claims after a paternity test proved her child was not Jordan's.

Michael Jordan and daughter Jasmine Jordan at Jordan All-Star With Fabolous 23 in 2012 in Florida | Source: Getty Images

Michael Jordan and daughter Jasmine Jordan at Jordan All-Star With Fabolous 23 in 2012 in Florida | Source: Getty Images

TAKING MICHAEL JORDAN TO THE CLEANERS

It was more than the long-suffering Juanita could bear, and in 2004 she once again filed for a divorce.

It would be two more years before the writ of divorce was approved by the courts, but Juanita's postnup and the evidence of Jordan's serial infidelities won her a mind-boggling settlement of $168 million.

The former couple has since worked out an amicable relationship, and are loving and devoted co-parents to their three children.

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