Rudy Giuliani was once dubbed “America’s mayor” by Oprah Winfrey, named “Person of the Year” by Time, and granted an honorary knighthood by the Queen of England. What happened?
But his work for Donald Trump has reportedly brought him to the brink of bankruptcy. When he tried to get paid for his services, Trump stiffed him. He now hawks collectible coins, health products, and cigars on his podcast, “Rudy Giuliani’s Common Sense,” and sells video messages on Cameo for four hundred dollars apiece. In April, he appeared on “The Masked Singer,” where he offered his rendition of “Bad to the Bone” in a rooster costume.
And alcohol does seem to be part of the story. Giuliani was always a red-meat, Scotch-and-cigars kind of person, but the drinking appears to have become serious after the debacle of his Presidential run, in 2008. That campaign was right out of the “New York mayor bombs on the big stage” playbook. In November, 2006, Giuliani was ranked the most popular politician in the country, and he went into the Republican primaries as the clear front-runner.
Florida, as it had for John Lindsay, dealt the fatal blow. The campaign had doubled down in the state , but Giuliani took only fifteen per cent of the vote, good for third place. He dropped out of the race, his campaign having burned through sixty million dollars and ended up four million in debt. He had one delegate. Giuliani’s career in national politics was over before it had properly begun. He and Judith were taken in by an old friend, who let them stay at his estate, Mar-a-Lago.
Because he governed the city during a period of recovery, and because his comportment on September 11th was exemplary, Giuliani came to be regarded as a paragon of leadership. This was not unjust. A lot of political success is timing and luck. If the city’s economy or crime rate had gone south owing to circumstances beyond his control, he would have had to take the blame.
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