The impeachment show has reached prime time. On Wednesday 13 November, millions tuned in to watch two senior US diplomats testify in the first public hearing of the inquiry into President Donald Trump’s behaviour in office.
At the core of the Democrats’ case is a phone call in August between Trump and Ukrainian president Volodymyr Zelensky. On the call, Trump dangles $400 million in US military aid to Ukraine as leverage in order to pressure Zelensky to investigate former vice president Joe Biden, his potential 2020 presidential rival. The call took place in July, one day after the Congressional testimony of Robert Mueller – the special counsel whose two-year investigation laid out evidence of obstruction of justice by Trump but stopped just shy of accusing him of actively colluding with Russian interference in the 2016 election. The impeachment inquiry was triggered after a whistleblower report – which the White House tried to suppress – leaked to the press. In response, Trump himself released an incomplete transcript of the call. He thought it exonerated him. It did not. Trump is shown responding to Zelensky’s mention of military aid: “I would like you to do us a favour though,” an apparently clear quid pro quo request. And as the story grew, one man quickly emerged as a central figure: Rudy Giuliani. Giuliani, most famous for having been mayor of New York City on 11 September, 2001, had been working for free for Trump as the president’s personal lawyer since April 2018 – but he featured more in the Zelensky call than any US diplomat. “Mr Giuliani is a highly respected man,” Trump tells Zelensky on the transcript the White House released. “He was the mayor of New York City, a great mayor, and I would like him to call you.” In fact, Giuliani had already spent months pressuring the Ukrainian government for dirt on Biden. As early as May, according to the Associated Press, Zelensky – newly-elected, and not yet in office – was huddling with advisors trying to figure out how to deal with the pressure Giuliani was transmitting on Trump’s behalf. As more of the story was uncovered, it became clear that Rudy’s work for Trump also included acting as a sort of unofficial under-the-table shadow US envoy – a one-man rogue State department. But, as the story unfurled, Giuliani unspooled. He was already notorious for gaffe-ridden, raging TV appearances on Trump’s behalf during the Mueller investigation and its aftermath, but this was next-level stuff. In one extraordinary meltdown interview with CNN’s Chris Cuomo on September 19, Giuliani admitted, seemingly by accident, that he himself had pushed Ukraine to investigate Biden – and, floundering, called Cuomo “a total sell-out”. How did Giuliani go from being the man widely beloved as “America’s mayor”, the man French president Jacques Chirac called “Rudy the Rock”, the man who was given an honorary knighthood by Queen Elizabeth, to this grotesque caricature? How did he go from being Time’s Person of the Year to a rolling media car-crash, whose every new TV appearance seems to further incriminate either himself, the White House, or both? I spoke with some of his past political adversaries as well as close aides and former friends to ask the question: what happened to Rudy – or was this Rudy there all along? Rudolph Giuliani was born in Flatbush, Brooklyn, in 1944, the only child of Tuscan immigrant parents. Giuliani’s father Harold was a small-time mob enforcer who had served time in Sing Sing prison for assault and robbery – an ironic twist, considering his son would make his name early in his career as a prosecutor of organised crime; in 1997 the New York Times would describe Rudy as the “crime-fighting United States Attorney, archenemy of the Mafia”. Rudy went to NYU law school, where he was appointed to the prestigious Law Review. After graduating, he volunteered on Bobby Kennedy’s 1968 Democratic presidential bid. But in 1975 he switched his party allegiance to independent so he could be recruited into the Republican administration of president Gerald Ford as associate attorney general. After some years bouncing between the Department of Justice and private practice, president Reagan appointed Giuliani US Attorney for the prestigious Southern District of New York in 1983. He quickly developed a reputation as a ruthless prosecutor, wielding media attention as a weapon with “perpwalks” – the humiliating marching-out of suspects in handcuffs in front of the press and the public. He got results. He prosecuted Ivan Boesky, a Wall Street speculator, and Marc Rich, a commodities trader, for insider trading – at a time when such rules were rarely enforced – winning huge settlements of $100m and $200m. In 1986, Giuliani successfully prosecuted 11 organised crime figures, including the dons of the east coast Italian mafia’s leading “five families”, in what Time magazine called “The Case of Cases”. These high-profile victories propelled him to fame, and fuelled his political ambitions. He first ran for mayor of New York unsuccessfully in 1989, the same year he stepped down from the Southern District at the end of the Reagan administration. Despite being a Republican, who even in the Reagan era were heavily outnumbered by Democrats in New York, he lost to popular incumbent David Dinkins by the narrowest margin in the city’s history. In 1993 he ran against Dinkins again – this time beating him by more than 50,000 votes, and carrying four of the city’s five boroughs. Rudy Giuliani’s rise and fall mirrors and, in a sense, prefigures that of Trump. The pair, born two years apart, have a lot in common. They are both New Yorkers but not Manhattanites by birth – Rudy from blue-collar Brooklyn and Trump from unfashionable Queens. They are both avid golfers. They are both multiple divorcées. Crucially, they both cut their teeth on a certain combative New York City style of news media, which gave both men a taste for fame – and the skills to cultivate it. Some of the parallels are downright eerie. The New York Times could have been describing Trump in 2019 when they wrote, during Giuliani’s 1997 re-election campaign, that the mayor “seems to believe in mayoral infallibility, at least so long as he is the Mayor. To question his righteousness is to risk his wrath. A devil’s advocate often seems regarded as the devil himself”. In the same article, former New York mayor Ed Koch said of Giuliani that “he can’t accept disagreement…When it occurs, he wants to destroy you. He goes for the jugular.” Asked what he was like as a political rival, Ruth Messinger, a former city councillor who was Giuliani’s Democratic challenger in the 1997 mayoral race, laughs. “Not fun,” she says. Describing Rudy’s political style as “nasty”, Messinger claims several supporters of her campaign received “threatening” phone calls from City Hall, and says she also remembers times when he threatened members of the press. “This is a man who divorced his wife at a press conference – that happened during the campaign,” she continues. “For me that always summed him up. You can’t expect what you think of as the limits of normal rational behaviour from this guy.” Messinger admits to a sense of schadenfreude from watching Rudy unravel on live TV. “I have to say I love watching it,” she says with relish. “He deserves to have some focused negative attention.” When she watches Giuliani today, Messinger says, “some of it – the focus on himself, he makes the rules, he draws the lines, interested in attention – some of that seems entirely familiar.” Nonetheless, she caveats, “some of it seems a little weird”. On the striking stylistic similarities between Giuliani and Trump, Messinger pointed to a common influence, Roy Cohn, the bombastic lawyer who was chief counsel to Joseph McCarthy and later worked for Trump. Giuliani’s approach was “very much Cohn’s style, the way he operated: pick people to pick on; assert your truth whether or not it’s the truth; and just be very strong and very centred about it, and you’ll cow a lot of people.” Rick Wilson, a Republican strategist who would become a vocal Trump critic after 2016, writing a New York Times bestseller called, Everything Trump Touches Dies, joined Giuliani’s reelection bid in 1997 as a media and advertising staffer. “The Rudy of 1997 was a guy trying to turn New York around,” he says. Wilson compares Giuliani to Batman: “People might not love his methods – but when there’s a crisis, they want Batman.” He says he never heard Giuliani mention Cohn when he worked at City Hall – though they were both New York characters on the legal scene and would certainly have been aware of each other, if not actually personally acquainted. Wilson also says that, though the Rudy and Trump moved in the same circles – as a deeply bizarre video of the pair (with Giuliani dressed in drag) from a charity event in 2000 shows – the two men had no long-standing friendship dating back before 2016, unless it was one they kept unusually secret. But the two men did share a rare and foundational life experience. Both ascended to fame in the same New York tabloid ecosystem, one defined by the New York Post and the gossip column Page Six. Both Trump and Giuliani “were very influenced by that as a model for media and public relations”, Wilson says. “It’s a school of… ‘Fuck you, I’ll say something more outrageous to distract you from the thing you thought was outrageous at first.’ That’s definitely an element of both men’s political approach, and Roy Cohn helped invent that”. But for Wilson, “Rudy is a serious person, or was; Trump is fundamentally unserious. Rudy is a guy who – for all his colourful presentation and affect – he really loved the city, he really loved it, and fought hard for it. Trump basically is a vampire squid who bleeds things until they’re corrupt of all value.” That leaves what Wilson calls the “weird unsolvable question”: what drove Giuliani to become, during the 2016 campaign, “the number one cheerleader, the number one advocate, the guy who absolutely would set himself on fire – and, in every way but literally, has – for Trump?”
“A lot of people ask me today: has Rudy changed? And my answer is: not really,” Norman Siegel, who was in Giuliani’s class at law school and later tangled with his mayoral administration as executive director of the New York Civil Liberties Union (NYCLU), tells me. “Those of us who battled with him as the mayor knew he was problematic back then, and he’s extremely problematic today.” The NYCLU was involved in an unprecedented 30 lawsuits against the Giuliani administration during his mayoral tenure – and were successful in 26 of those, Siegel tells me. Siegel says he saw in Giuliani’s mayoralty hallmarks which would later come to be core to Trumpism – in particular a combative relationship with the media that blended contempt with a desperate need for attention, as well as a scorched-earth approach to political warfare and a certain flexibility in their approach to the truth. Siegel, who briefly served on a mayoral task force on police misconduct until Giuliani abruptly shuttered it five months in, says euphemistically that Rudy was “not very empathetic to people who were – why don’t we say, racially different than he was”. He spells it out: “…which means people of colour.” Sal Albanese, another New York City councillor, says he admired Giuliani at first for his work prosecuting mafia bosses. “He did make some very good gains in terms of organised crime and corrupt political leadership…and then he became mayor,” he says. Then it was “constant battles with his administration over policy, the fact that they were chronically lying…he was just generally a liar”. “He would not hesitate to use information about folks who oppose him; leak to the press,” Albanese says. “I know at least one city council member who criticised Giuliani was brought into the office and a file was opened, and they warned him that if he continued they would leak this information to the press.” “If you crossed him in any way he would go all out to destroy you.” Albanese says. Like Siegel, he says that when people ask him, “what happened to Rudy?” he answers: “Well, nothing happened to Rudy. He’s still the same Rudy. Mean. Vindictive. He’s a chronic liar, and will do anything to gain whatever his objective is – in other words, the ends justify the means.” After Giuliani beat Messinger to win reelection in 1997, Wilson went to work for him in City Hall. Nominally in an advisory capacity, he was really there to start “battlefield preparations” for Giuliani’s planned New York Senate race – which would have pitted him against Hillary Clinton in 2000. That bid didn’t pan out, partly because Giuliani developed prostate cancer, “which was horrifying in every way,” Wilson says, and partly because the mayor spent much of the year embroiled in a messy and public divorce from his second wife, Donna Hanover. Which is why, when Giuliani entered the final months of his second and last mayoral term, it seemed as if he was at the end of his career in public service. “There’s a good argument you could make that Rudy would have gone off and had a radio show, and been a lawyer again,” Wilson says, almost wistfully. “If 9/11 hadn’t happened.” Most people I spoke to for this story, even many of his political opponents, praise Giuliani – to at least some extent – for his leadership after the terrorist attacks in New York on September 11, 2001. “After 9/11, we have to give him credit, he was a real good leader here,” the NYCLU’s Siegel says. “History sometimes calls people, and they sometimes answer, and that was his moment,” Wilson says. “No matter what his flaws were as a mayor sometimes, he was the right man at the right moment at that day.” Giuliani, Wilson says, attended every funeral of the hundreds of firefighters and police who died in the attack. “Every single one. Every single funeral. Did the last honours for all those guys.” “It makes the current tragedy more painful to watch,” Wilson adds. “The guy from those days that went out there and cried with the families, and laid these guys to rest, and took on some of that horrible terrible weight. For all of his flaws, he got from the public an enormous sense of both gratitude and latitude.” For Wilson, that still carries weight. “There is a deep sense of tragedy about all this,” he says of Giuliani’s humiliation in the Ukraine scandal. “There’s a sadness about it.”
On October 10, 2019, two Soviet-born businessmen with ties to Giuliani – Igor Fruman and Lev Parnas – were arrested at Washington DC’s Dulles international airport with one-way tickets out of the country. According to court documents, the pair had made half a million dollars in illegal campaign donations to the Trump campaign and associated Political Action Committees, apparently in the hope that it would buy them assistance from Trump and Giuliani in setting up a scheme to sell liquefied natural gas to Ukraine. In order to do that, they wanted the removal of Marie Yovanovitch, who was then the US ambassador to Kiev, in favour of a diplomat who would look more favourably on the endeavour. Trump, on the phone call at the centre of the Ukraine scandal, describes Yovanovitch as “bad news”. Reached by the Associated Press for a response at a baseball game, Giuliani claimed: “I have not pursued a deal in the Ukraine. I don’t know about a deal in the Ukraine. I would not do a deal in the Ukraine now, obviously. There is absolutely no proof that I did it, because I didn’t do it.” But according to CNN, Giuliani had been in contact with Parnas since November 2018. Reuters reported in October that Parnas’ company – Fraud Guarantee, based out of Boca Raton, Florida – paid Rudy’s consulting firm, Giuliani Partners, $500,000 for “business and legal advice”. The way Rudy tells it, Parnas introduced him to Ukraine’s former chief prosecutor, Viktor Shokin, who told him that he had been forced out of his job in 2016, at then vice president Biden’s urging, because, Shokin claimed, he was investigating a company where Biden’s son sat on the board. The core story does not hold up: Giuliani has produced no evidence that Biden’s son Hunter was under investigation at all, let alone any evidence of any wrongdoing, and Joe Biden was one of many global leaders calling for Shokin’s removal on corruption grounds at the time. Either Rudy truly believed the story, or he didn’t care whether it was true – perhaps because he thought it would bear political fruit against Biden, who was the Democratic frontrunner to face Trump in November 2020. Whichever of those is true, the result is the same: Giuliani’s pursuit of that narrative via back-channels backfired so hard that it triggered an impeachment inquiry. What drew Giuliani to Trump’s flame? He was wealthy – after his second term as mayor was over in 2002, Giuliani started his own consulting firm; he later also joined a white-shoe New York law-firm, catering to big business. His post-9/11 celebrity made it easy for him to make a fortune; according to tax documents revealed as part of court proceedings in 2018 pertaining to Rudy’s divorce from his third ex-wife, Judith Nathan, Giuliani made $7.9 million in 2016 and $9.5m in 2017. Despite this, rumours are swirling in Rudyworld that Giuliani may now be on the verge of bankruptcy. Contesting Nathan’s claim against her ex-husband in court, Giuliani’s lawyer claimed that since agreeing to represent Trump for free, the former mayor lacked the funds to maintain his ex-wife’s lifestyle. At the same time, his public behaviour has been the subject of speculation; in television studios, Giuliani can come across as barely under control. The wild-eyed and ranting Rudy we see regularly on TV these days, a former senior aide says, was someone they recognise, but used to only see rarely – at the end of the occasional long evening, after one or two cocktails too many. According to the Washington Post, Trump and Giuliani speak all the time on the president’s private phone. The former mayor’s stock with Trump had been high as he successfully shielded him from Mueller with a strategy of minimal personal co-operation. Trump and Giuliani’s hardball Roy Cohn-esque approach of attacking Mueller and his inquiry as a “hoax” and a “witch hunt” may have worked in the fallout from the Russia collusion inquiry. But Giuliani’s dealings in the Ukraine, trying similarly to smear Biden, has got them into much deeper trouble – so much so that former National Security Advisor John Bolton described Rudy in Ukraine as “a hand grenade who’s going to blow everybody up”. How does this end for Rudy? “I think Trump will fuck him,” Wilson, Giuliani’s former ad man, says. “They will make him the fall guy. Trump has no loyalty to anyone. No matter what they do for him, no matter how hard they work for him, he will fuck over every single person in his path, and I don’t think there’s any scenario where Rudy doesn’t lose.” Portrait photograph Spencer Heyfron / Redux / eyevine, all other photographs Getty Images