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He has a net worth estimated at 45 million US dollars (62 million Australian dollars) and has never hesitated to spend his money.
But now, Rudy Giuliani, a notoriously successful Trump attorney, said he could not afford to pay his ex-wife's child support because divorce proceedings were becoming more and more ugly.
Mr. Giuliani, former mayor of New York City, separated from his third wife, Judith Nathan, in April, after 15 years of marriage.
He announced that he was attending the Republican Jennifer LeBlanc fundraiser in June, and also forged relationships with alleged mistress Maria Rosa Ryan.
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The couple's divorce is now before the courts – and apparently, the 74-year-old millionaire suddenly screams to poverty.
according to The daily beastMs. Nathan, 63, claims $ 63,000 ($ 86,600) in spousal support, which adds to the shelter costs of six homes and incidental expenses, including membership fees to several country clubs ".
But Mr. Giuliani, a father of two, said he currently has financial difficulties.
The two men appeared before the New York Supreme Court earlier this week, and Nathan's lawyer Bernard Clair said the father of two had spent more than $ 900,000 ($ 1,240,000). ) since the breakup in April.
Mr. Clair stated that Mr. Giuliani spent US $ 7,131 in fountain pens and US $ 12,012 (AU $ 16,527) in cigars during this five-month period.
He also spent $ 286,000 ($ 393,507) for his alleged mistress, $ 447,938 ($ 616,317) "for his own pleasure" and $ 165,000 ($ 227,023) for a personal trip.
He also claimed that Giuliani could not claim financial hardship because he had agreed to represent US President Donald Trump for free in April.
Mr. Clair stated that his client's ex-husband used "conduct that can only be described as SIDS … Sudden Income Deficit Syndrome".
"Mr Giuliani took the initiative to radically change the financial status quo that prevailed before this action," The daily beast reported Mr. Clair.
Documents also revealed that Mr. Giuliani earned US $ 9.5 million (A $ 13 million) in 2017 and US $ 7.9 million (A $ 10.8 million) in 2016.
At the same time, Giuliani's lawyer, Faith Miller, said his client had already paid Ms. Nathan about 1 million US dollars ($ A1.37 million US) in fees since the separation.
Mr. Clair stated that Ms. Nathan was not concerned with her ex-husband's new relationship.
"My client is not interested in romantic interest or otherwise, she really does not like it," said Mr. Clair, according to The daily beast.
"What matters to her is that these expenses for these people continue, while she has not received any direct assistance since August of this year, not a penny directly for her."
Giuliani also bitterly divorced his second wife, Donna Hanover, who was finally paid in 2002 for more than US $ 6.8 million (A $ 9.3 million).
He served as mayor of New York from 1993 to 2001, year when he tried unsuccessfully to enter the national political life.
The bulk of his fortune comes from his consulting firm, Giuliani & Company, which he founded towards the end of his tenure.
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