How Rudy Giuliani and Donald Trump’s Toxic, Twisted Bromance Nearly Drove the Country Off a Cliff

Inside the Hive host Brian Stelter talks to Rudy Giuliani biographer Andrew Kirtzman and Vanity Fair executive editor Claire Howorth about the epic fall of “America’s Mayor” and his yearslong, symbiotic relationship with Donald Trump. “There’s something about Rudy that makes Donald Trump swoon,” says Kirtzman.

A veteran political reporter, Kirtzman considers the Giuliani saga to be “one of the great rise and fall stories of our lifetime.” He recalls Giuliani being an “extraordinary prosecutor” and was alongside him on September 11, remarking that the former New York City mayor acted as a “calm, fatherly general.” 

“The Giuliani that I watched from two feet away that whole morning was, if anything, more impressive than the Giuliani that people watched across the world on television,” Kirtzman says, adding that “there was a reason he became the most admired man in America for a short time.” But Kirtzman watched Giuliani spiral after his failed 2008 presidential bid, and sink even lower in the aftermath of the 2020 election.

When asked what happened to Giuliani, Kirtzman says that if “you had to boil it down to one word it would be ‘desperation.’ It would be desperation for power and money kind of on the way up, and then desperation to recapture his relevance, his fame after he lost the 2008 presidential race.” It’s after that letdown that Giuliani “went downhill into the clutches of Donald Trump’s arms, it was the flameout of his race for president.”

More recently, of course, Giuliani was central to Trump’s first impeachment, over pressuring Ukraine for dirt on the Bidens, and his second, in advising the president as he tried to overturn the 2020 election. Giuliani appears to be co-conspirator 1 in the DOJ’s latest indictment of Trump and may face charges himself in Washington, DC, as well as Georgia. 

“I think that Giuliani will never admit any kind of fault,” says Kirtzman, adding: “He is never going to admit that he was wrong about anything. And right now, he’s throwing spaghetti against the wall, just like hoping something will stick, hoping he can muddy the waters, but he’s in terrible trouble.”