After Rudy Giuliani's recent, potentially troublesome media tour as President Trump's new lawyer, the former New York City mayor's behavior has left many Americans shocked and confused. But on Sunday's Last Week Tonight, John Oliver argued that Giuliani's "always been this way," detailing his various controversies and bizarre public moments.
Before his deep dive into Giuliani's past, Oliver summarized the shocking comments from the former politician's recent TV blitz – including that Trump repaid his attorney Michael Cohen for a $130,000 hush-money payment to porn actress Stormy Daniels. Giuliani also "undercut the White House's official line on why James Comey was fired, prematurely announced the release of American hostages from North Korea (something that, as of this taping, has still not happened) and made [a] creepy comment about what would happen if prosecutors targeted Trump's daughter," calling her "a fine woman."
Many Americans who remember Giuliani as a steadying presence on 9/11 have found these statements disorienting. "People seem to be as shocked at finding out who Giuliani really is as a child at Disney World who accidentally saw Mickey Mouse pull off his head to reveal that he's actually Tilda Swinton," Oliver cracked.
From there, the host traced Giuliani's history – from his time as a federal prosecutor through his first marriage to a second cousin. "He didn't think it just a little bit weird at the wedding ceremony when one side of the church was both families and the other was just one nervous photographer who didn't take a single picture?" Oliver joked.
The host also touched on Giuliani's "unrelentingly abrasive personal style" as mayor – including his heated exchanges with constituents on a local radio show (including one notorious argument over ferret ownership) and his "tough-on-crime stance with a severely increased police presence and an aggressive crack-down on so-called 'quality of life crimes' like panhandling and jaywalking."
At one point, Giuliani moved out of the Mayor's residence amid accusations of an extramarital affair. During a news conference, he told the media that he intended to separate from his wife – without having informed her first.
Nonetheless, Oliver said, the former mayor "cashed in" on the public's goodwill after 9/11: writing a book, delivering speeches that earned up to $200,000 a pop, launching a consulting firm, becoming a partner in a law firm and even running for the 2008 presidency. Then, in January 2017, he arrived in Trump's circle as a cybersecurity adviser – a pairing that Oliver argued makes perfect sense.
"When you look at all of this in total, you realize that Giuliani's role as Trump's lawyer isn't an aberration: Everything in his life has led to this point," the host said. "And while he may well be providing terrible legal representation for Trump, he's actually the most honest representation of him in general. Because think about it – they're basically two versions of the same person. They're both New Yorkers coasting on their reputations; they both had three marriages; neither of them can shut up when in front of a camera; and, perhaps most importantly, they both want to fuck Ivanka – which is weird for Trump because Ivanka is in his family, and it's weird for Giuliani because she isn't."
Oliver isn't sure what will come of Giuliani's Trump tenure, but the host made preparations for one possibility: "Maybe he brings Trump down through sheer incompetence. Maybe he gets fired in the next two weeks. Although, to be honest, at the rate we're going, he is so fatally flawed as a human being that he's probably going to end up president. Although to do that, he'll need a campaign website, which he might find difficult. Because, for the record, Rudy, giuliani2024.com is no longer available because we bought it, and it links to a dancing ferret giving you the finger."