Trump's Friend And Former Lawyer Rudy Giuliani Went From 'America's Mayor' And Person Of The Year With A $100 Million Net Worth To Penniless And Facing Prison — Ex-Wife Says 'They Were Burning Through $250,000 A Month On Sheer Fun'

At one time, Rudy Guliani was one of the country's most admired politicians, earning the title of "America’s Mayor" after his leadership during the 9/11 attacks. He graced the cover of Time Magazine as Person of the Year in 2001, but in the years that followed, his life took a drastic turn. 

He's known for his legal defense of former President Donald Trump, his controversial statements and his involvement in attempts to overturn the 2020 presidential election. Giuliani is now charged with 13 crimes related to the election and dealing with a slew of financial troubles. 

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Before taking the helm as mayor of New York City in 1994, Giuliani was a prosecutor, earning a modest salary from the state of New York and the federal government. He was far from being a millionaire.

After 9/11, he amassed significant wealth, thanks to lucrative book deals, high-priced speaking engagements and a flourishing consulting business. In 2003, during a divorce, he declared his net worth at $3 million. In 2007, during his bid for the presidency, his financial disclosure revealed a net worth of between $18 million and $70 million. A decade later, it was estimated to be as high as $100 million or more.

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But recent years have presented many challenges for Giuliani. Legal and financial woes have taken center stage. The IRS came knocking, claiming he owed nearly $550,000 in unpaid income tax for 2021 and slapped a lien on his $4.5 million Palm Beach penthouse. 

Giuliani had a golden opportunity to invest his considerable wealth in startups and ventures that could have turned his $100 million into a financial empire. Instead, he's now grappling with tax liens, financial instability and legal consequences. He could have been an early investor in Uber Technologies Inc., Tesla Inc. or Apple Inc. Instead, he wasted his millions. Anyone has the opportunity to invest in startups as a potential way to be an early investor in the next big thing, but seizing that opportunity requires foresight, risk-taking and wise financial management — qualities that Giuliani, despite his substantial resources, did not effectively use.

Andrew Kirtzman, a biographer who's been tracking Giuliani's journey, sheds light on the matter, emphasizing how Giuliani "squandered it." Kirtzman referenced Giuliani's extravagant lifestyle, citing divorces and monthly expenses that would boggle the mind. He said, "Giuliani has squandered it. He's had several divorces. He lived very high, his ex-wife said that they were burning through $250,000 a month on sheer ‘fun.' A month! I mean, he lived very well, and now he's penniless and facing prison."

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