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The man once known as America’s Mayor may soon have to fork over some of his most prized possessions, including several New York Yankees World Series rings, to pay off a massive debt owed from a defamation lawsuit settlement.

During his tenure as New York City Mayor from 1994 to 2001, Rudy Giuliani became one of the most well-known political figures in the country. He was able to help revitalize the city’s economy and make it a premiere global tourist destination once again.

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The former district attorney also gained a lot of fans in the city through his unabashed love for the New York Yankees during their run as the sport’s lone dynasty team. It was the perfect marriage of sports and politics. And it benefited the team and Giuliani, as he was gifted honorary World Series rings from some of their championship seasons during that era.

However, with the rise of former President Donald Trump, the narrative on the legendary NYC mayor has changed over the last decade. Following Trump’s election defeat in 2020, Giuliani was one of the most public surrogates falsely pushing claims of election fraud. Especially in Georgia where he helped wage a campaign against a pair of election workers.

Court order is forcing Rudy Giuliani to give up Yankees World Series rings to pay off massive debts

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Those false claims led to a defamation suit last year from Ruby Freeman and Wandrea “Shaye” Moss. And an eventual ruling that Giuliani must pay the two plaintiffs $148 million in damages. The former mayor has cried poor since the ruling, and it was revealed by the Associated Press this week that lawyers for Freeman and Moss are asking a district court in New York to force Giuliani to hand over his apartment and other property to pay for the settlement.

“Lawyers for Ruby Freeman and Wandrea “Shaye” Moss urged the U.S. District Court in Manhattan to force Giuliani to turn over his Madison Avenue apartment, any remaining cash, and some of his prized New York Yankees memorabilia, including three World Series rings and a signed Joe DiMaggio shirt,” the AP reported.

“Freeman and Moss also staked a claim to about $2 million Giuliani has said Donald Trump’s 2020 presidential campaign owes him and they sought to take control of another Giuliani property — his Palm Beach, Florida, condominium — through another legal mechanism known as receivership.”

The long-time Yankees fan abruptly filed for bankruptcy days after the defamation suit settlement last year.

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