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The Reason Oprah Winfrey’s Ex Randolph Cook Sued Her After Their Break-Up

The Reason Oprah Winfrey’s Ex Randolph Cook Sued Her After Their Break-Up

Oprah/Instagram.

Oprah Winfrey is a renowned media personality, talk show host, philanthropist, and influential figure in the entertainment industry. Her journey has been punctuated by legal challenges of various kinds, ranging from business disputes to personal entanglements. The renowned talk show luminary has faced many lawsuits, from former romantic partners to business adversaries. 

In 1998, some Texan cattle ranchers took legal action, seeking to attribute the dramatic plummet of beef prices to Winfrey’s actions. This plunge, which amounted to an $11 million loss in revenue for the ranchers, was associated with Winfrey’s discussion of contentious practices in the beef industry on her show. Despite the allegations of defamation against the industry, a jury’s verdict vindicated Winfrey, affirming the power of free speech.

In another episode, Winfrey’s philanthropic pursuits in late 2007 led to a distinct legal clash. Her establishment of a boarding school for girls near Johannesburg, South Africa, was marred by a scandal involving a dorm matron accused of numerous counts of sexual abuse. Amid the turmoil, Winfrey blamed the school’s headmistress, Lerato Nomvuyo Mzamane, for purportedly failing to communicate the allegations. In response, Mzamane filed a defamation lawsuit against Winfrey in 2008. Subsequently, the two parties reached an out-of-court settlement in 2010, ending the legal strife.

While most legal disputes intersected with Winfrey’s professional pursuits, few delved into her personal affairs. Notably, one such case was brought forth by Randolph Cook, a self-proclaimed former boyfriend, who aimed to unearth Winfrey’s undisclosed secrets. Cook’s claims added another layer to the array of legal challenges after Oprah Winfrey’s endeavors.

Randolph Cook’s Legal Battle: Claims He Tried to Tell the Story of Living with Oprah Winfrey

Randolph Cook says he lived with Oprah Winfrey in Chicago from January to May 1985. During this time, they used drugs, as reported by the Chicago Tribune. Cook wanted to write a book about their time together when they went their separate ways. But Oprah stopped him, so Cook took her to court in January 1998. Cook said, “Upon notification of my intent to publish my life story, Ms. Winfrey expressed outrage to the disclosure of truth and fact.”

Cook wanted $20 million because he believed Oprah Winfrey had slandered his reputation by falsely accusing him of lying. The National Enquirer quoted Oprah from court papers as saying, “I will fight this suit until I am bankrupt before I give even a penny to this liar.” Cook also said Oprah caused him distress. He added, “She threatened everyone involved with my intended publication, causing great financial loss.” After some time, Cook changed his case to say that Oprah hurt his reputation and stopped him from making money.

Kathy Hutchins/Shutterstock.

The court didn’t agree with Cook’s case, but some of their choices were changed when he asked them to look again. In a book by Kitty Kelley called “Oprah: A Biography,” it says that the case was supposed to be decided by a group of regular people, but Cook stopped the case before they could decide. He did this because his mom was very sick. In 2007, Cook finally shared his side of the story in a book called “The Wizard of ‘O’: My Life With Oprah, The L. Randolph Cook Interviews.”

However, Oprah still maintains she was never in a relationship with Cook.

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