Once upon a time, Rudy Giuliani was one of the most respected politicians in the country. Following his conduct as mayor of New York City after the 9/11 attacks, he was a national hero. He parlayed that fame and heroics into a fortune through book deals, personal speaking fees and a lucrative consulting business.

Prior to being elected mayor of New York, Rudy had spent about two decades earning a modest salary as a prosecutor for the state of New York and Federal government. He was not a millionaire when he served as mayor from 1994 to 2001.

Thanks to the aforementioned book deals, speaking fees and consulting business, by 2003 when he was going through a divorce, Rudy estimated his net worth at $3 million.

Just four years later, when he was running for President in 2007, Rudy’s financial disclosure estimated his net worth in the range of $18 to $70 million. A decade later his net worth was perhaps as high as $100 million.

As you know, Rudy’s life and reputation have taken a bit of a weird turn in recent years. And according to longtime Giuliani biographer Andrew Kirtzman, in a recent interview with CNN, Rudy’s legal problems have left him “penniless.”

That accusation may explain why Giuliani was recently sued by his former lawyer Robert Costello over $1.36 million in alleged unpaid legal fees in various cases against him, primarily the charges in Georgia over his involvement in attempting to overturn the 2020 presidential election on behalf of Donald Trump. Giuliani was one of several alleged conspirators charged in that case, and he’s also facing a civil court for his alleged defamation of two election workers. Kirtzman laid it all out like this:

“Costello has represented him through four investigations – three of them criminal – 10 civil suits, two disbarment hearings. And I don’t even know if that includes the sexual harassment suit by a former employee. I mean, Giuliani has just this deep attraction to danger and you know, he has no one to blame but himself.”

Chip Somodevilla/Getty Images

Facing the kind of legal hot water that Giuliani is can be pretty tough even when you’re rich, but according to Kirtzman, Giuliani is nowhere close to where he was 20 years ago in terms of personal finances:

“Well, I mean, Giuliani’s going broke. He’s going broke and he’s facing prison. And, you know, his catastrophic fall is just one of the great, kind of, rise and falls of our generation. I mean, Giuliani was once worth $100 million. His Giuliani Partners was founded right after 9/11 to capitalize on his 9/11 fame. The place made $100 million over five years.”

Kirtzman went on to point out that Giuliani’s financial fall isn’t attributable solely to his recent legal troubles or any other single factor. Instead it’s a culmination of forces he says have been swirling around the former New York mayor for years:

“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. It’s an extraordinary story.”

What’s Giuliani doing to make ends meet? It’s been reported that in July he listed his upscale Manhattan apartment for sale with an asking price of $6.5 million but hasn’t yet managed to find a buyer. He’s also become active on the custom video platform Cameo. And earlier in September, Donald Trump reportedly held a $100,000-a-plate fundraising dinner for his beleaguered associate at his golf club in Bedminster, New Jersey.

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