Giuliani's take-charge response to the terrorist attacks of September 11, 2001, won him much respect — not to mention requests to share his insights at well-paid speaking engagements, to the tune of $300,000 per pop (via Yahoo! Finance). In 2006 alone, he earned $11.4 million for 124 speeches. Note that this was one full decade before he became part of the inner circle of the 45th U.S. president. As of 2018, he was earning between $5 and $10 million a year, according to Time.
So what does "America's Mayor" spend all of his mega-millions on? His ex-wife's divorce attorney, Bernard Clair, told New York Justice Michael Katz that although at the time, Rudy had claimed he was having "financial difficulties," his expenses between April and November 2018 alone tallied more than $900,000 on a variety of personal indulgences. This included more than $12,000 on cigars, more than $7,000 on fountain pens, and close to $300,000 on his alleged mistress Maria Rosa Ryan (per New York NBC affiliate).
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