Even Trump is said to find Giuliani an embarrassment – so why does he keep him around?

The terrible twosome are both clinging to the mast of their wrecked vessel

Harriet Alexander
New York
Wednesday 16 December 2020 21:35 GMT
Rudy Giuliani's hair dye drips down his face during press conference

For a reality TV star president who is writing his own script within the White House, it is a matter of great importance that your stars look the part.

On the first day of his presidency, Donald Trump heaped his highest imaginable praise on his then-defence secretary, Jim Mattis. “This is central casting,” he said. “If I was doing a movie, I pick you, general.”

Mike Pence, his vice president, was also deemed "central casting". "So wonderful to work with, a real talent, a real guy,” said Mr Trump. "And he is central casting, do we agree? Central casting. He's been great."

Brett Kavanaugh, his nominee to the Supreme Court, was another case in point. “I said, you are so central casting,” he recalled at a Tennessee rally. “Great marks, great schools, the best everything, the best of everything.”

So what must the director have felt watching one of his stars quite literally melt down in front of him? Rudy Giuliani, head of his "elite strike-force" of election lawyers, stood before the cameras sweating profusely, with hair dye dripping down his cheeks. That was after his memorable press conference at the Four Seasons Total Landscaping, on 7 November.

He raged against ballot machines switching votes surreptitiously, and about dead-of-night crews entering the polling stations to meddle with the tallies. His face, cruelly captured at its most wild-eyed and lunatic moment, was on the front page of newspapers around the world.

Even for a showman lawyer, working for a showman president, the spectacle was too much. Mr Trump thought the 19 November presentation made him “look like a joke,” The Washington Post reported one campaign official who discussed it with him as saying.

The president felt "humiliated" by Mr Giuliani's performance, said the Associated Press's White House reporter, Jonathan Lemire. Mr Trump was "growing angry and frustrated" with Mr Giuliani, according to Mr Lemire. He was still talking to him but had told people around him in recent days he "felt like Giuliani had oversold his legal case”.

“The president was humiliated by watching Giuliani on stage in that news conference with the hair dye streaking down his face. He recognised that there was really no ‘hail Mary’ coming here; he’s angry at Giuliani he had led him down this path.”

The hair dye press conference came in the midst of an astonishing two months – astonishing even by the standards of someone who has had a remarkable romp through the decades.

In October he had made a stomach-churning cameo in Sacha Baron Cohen’s new Borat film, getting very cosy during an interview with a “journalist” and then retiring to the bedroom with drinks and beginning to undo his trousers. He insisted it was because he was removing his microphone. Then came the Four Seasons press conference, followed by the hair dye escapade. 

He hitched his wagon to a Wacky Races cast of characters, which include the leopard-print loving, conspiracy theory obsessed attorney Sidney Powell, to the Michigan IT worker who decided to spar with the state politicians hearing her account and later had to confirm she was not drunk.

Hair dye runs down Giuliani’s cheek during a bizarre appearance at a press conference (Getty)

He criss-crossed the country championing Mr Trump’s cause, catching Covid-19 in the process and forcing the closure of the entire Arizona state legislature amid fears of an outbreak sparked by his visit.

Mr Giuliani’s biographer Andrew Kirtzman wrote: “He has become a punchline, captured in a bedroom with a young woman in a movie; staging a news conference at the wrong Four Seasons; dripping hair dye and introducing a stream of cartoon characters as witnesses in a political conspiracy case that the courts aren't buying. His credibility is dissolving, one disaster at a time.”

Yet, against all odds, Mr Trump refuses to discard Mr Giuliani. As the rats abandon the sinking Trump presidency, only set on saving themselves, Mr Trump and Mr Giuliani are sticking together, clinging to the mast of the wrecked vessel.

Even being admitted to hospital with Covid-19 on 7 December couldn’t distract Mr Giuliani from his crusade. Less than 24 hours after entering Georgetown University Hospital he was back on Twitter: “A MUST WATCH – VIDEO EVIDENCE FROM GEORGIA!” he wrote. It's the final chapter in a scriptwriter’s-delight of a saga.

From the beginning, they were close – geographically, at least. The two men grew up around 10 miles from each other – Mr Giuliani in the East Flatbush area of Brooklyn, Mr Trump in palatial splendour in Jamaica Estates, Queens.

Their lives charted parallel patterns: both men married three times, revelling in the tabloid circus that followed them around, battling their former flames, mistresses and ex-wives in the press.

In the early days of the Trump presidency, Mr Giuliani – mayor of New York between 1994 and 2001, “America's mayor”, given an honorary knighthood by the Queen for his leadership after the 9/11 attacks – bought Mr Trump a perception of political clout.

Mr Trump, meanwhile, gave Mr Giuliani access to the White House – something he had long coveted, a dream which culminated in a failed 2008 primary bid. Yet while for Mr Trump the presidency is the pinnacle, for Mr Giuliani it represents an ignominious end.

Giuliani is elected mayor of New York in 1993 after losing his previous attempt (AFP/Getty)

"He's the one who was prosecuting under the Rico act, the way I understand it," said Robert De Niro – a reference to the Racketeer Influenced and Corrupt Organizations Act that the former "mob buster" used to great effect against organised crime. "And now he's representing a mob family. It's crazy. I don't know what happened to him. I feel bad for him."

Late-night comic Stephen Colbert noted: "Telling your kids that Rudy Giuliani was once respected is like explaining that OJ Simpson was once a football player."

Yet respected he was.

Mr Giuliani worked his way up as a prosecutor in the Southern District of New York – one of the most influential jurisdictions in the US – and was appointed to head it in 1983 by Ronald Reagan. He is remembered as a charismatic and forceful leader, who bolstered the reputation of the office with his high profile and headline-grabbing prosecutions.

Giuliani attempts to shush alleged voter fraud witness

Among those he "took down" were the five heads of the New York crime families – a feat that, to some, seemed impossible. The Mafia Commission Trial gripped New York from February 1985 until November 1986 – Time magazine described it as the most important mob trial since the Chicago mafia was broken up in 1943.

He attracted attention to white-collar crime cases, not without controversy, by ordering “perp walks” of Wall Street executives being led in handcuffs from their bustling trading floors.

Mr Giuliani, ever the showman, also took centre stage in some of his trials. He was the lead prosecutor in the high-profile public corruption trial of Stanley Friedman, the chairman of the Bronx Democratic Party, who was charged with racketeering and bribery. Mr Giuliani cross-examined Mr Friedman, who testified in his own defence, and secured his conviction.

His deputies included former FBI Director James Comey, who wrote about his former boss in his 2018 memoir, A Higher Loyalty.

“As a young prosecutor I found his brash style exciting, which is part of what drew me to his office,” Mr Comey wrote. “I loved it that my boss was on magazine covers, standing on the courthouse steps with his hands on his hips, as if he ruled the world. It fired me up.”

Mr Giuliani got so much attention, Mr Comey wrote, because he demanded it. "The most dangerous place in New York is between Rudy and a microphone," he said.

Mr Giuliani enjoyed the fame, leveraging the role into one of even greater power – that of mayor of New York, ruling the nation's largest city.  

Outside the wrong Four Seasons, a press conference that is now notorious (Getty)

In 1989, he made his first run for mayor. Mr Trump at that point was a brash and self-aggrandizing real estate mogul who placed full-page ads in New York newspapers calling for the death penalty for the Central Park Five, a group of black and Latino teenagers from Harlem who were accused, convicted and imprisoned for a rape it later turned out they didn’t commit.  

That year, Mr Trump co-chaired Mr Giuliani’s first campaign fundraiser, and donated $3,000 (£2,200) to Mr Giuliani’s campaign. Mr Giuliani lost to David Dinkins, but won on his second attempt, in 1993.  

Running on a "tough on crime" ticket, it was a job he relished – rushing to the site of crimes and catastrophes, with the press trailing in his wake.

“As mayor, Giuliani transformed New York City from a permissive and disordered society in which criminals, vagrants, bureaucrats, racial charlatans, and public-sector unions ran roughshod over taxpayers, to a socially healthy and financially solvent metropolis worthy of its “Capital of the World” moniker,” gushed Craig Trainor, a criminal defence and civil rights attorney in New York City, in an article for the conservative Federalist Society.  

Out of hours, he would relax at Club Macanudo, an Upper East Side cigar bar, and hold court beneath a large painting of well-known cigar smokers living and dead, including John F Kennedy, Sigmund Freud, Jack Nicholson and Julie Andrews.

He toyed with running for the Senate in 2000, and Mr Trump endorsed him as “the greatest mayor in the history of the city of New York”, again donating to his campaign. “He’s the best,” said Mr Trump.  

Corruption starts with ‘yes-men’ and women, the cronies who create an echo chamber of lies and subservience to maintain their proximity to power

In a sketch for the 2000 Inner Circle Show, a satirical performance put on by New York City’s political reporters, the friendship between the two brash publicity seekers was hammed up for the delighted crowd.

Mr Giuliani was in drag, and smooched by Mr Trump, who then buried his face in Mr Giuliani’s faux bosom. Mr Giuliani reacted in mock horror, in a video which refuses to die on the internet.

When the Twin Towers were hit, Mr Giuliani was at his finest. He had been at a breakfast in midtown Manhattan when the plane hit the first tower, and sped south to the site. At 9.59am, when the first tower came down, Mr Giuliani was two blocks away, in an office on Barclay Street, trying to get the vice president on the phone. His deputy, Rudy Washington, back at City Hall, didn't know if he had survived.

The mayor emerged blinking from a basement tunnel, his head and shoulders dusted white with ash in yet another, unintentional this time, made-for-tv moment. He walked and talked for two miles, comforting a police officer, marshalling reporters and calling in to a television station to urge calm.

The terrible twosome: Giuliani and Trump walk down the runway during the NYC2000 fashion show (AFP/Getty)

At a press conference later that day, he was asked how many had died. “The number of casualties,” he said, “will be more than any of us can bear ultimately.”

It was what the city needed – honesty, guidance, reassurance, visible leadership. For his role, the Queen gave him an honorary knighthood. But, as ever, there was an edge.

"That time was absolutely the best and worst of Rudy," said Frederick AO Schwarz Jr, the city’s former corporation counsel under mayor Edward Koch. “Rudy stood up strong and rallied us. But that confidence created the very dangerous idea that we couldn’t survive without him.”

Cracks had, of course, already begun to show long before 9/11. When his police chief, Bill Bratton, saw his profile rocket, in the light of successful crime-reducing policies, Mr Giuliani was unamused. His popularity in opinion polls exceeded that of any local public official, including Mr Giuliani. A 1996 Time magazine cover for Mr Bratton was the final straw; in March 1996, Mr Bratton submitted his resignation.

Then there was his private life. In May 2001 his second wife, of 16 years, journalist Donna Hanover, found out at a press conference that he was leaving her.

The couple had two children – Andrew, now 34, working at the White House and Mr Trump's golf partner of choice, and Caroline, now 31, a filmmaker busy attacking her father in Vanity Fair.

Mr Giuliani made a public announcement referencing his long-rumoured mistress, who he had met in 1999. He had taken her everywhere with him since they first met – to Yankees games in the summer of 1999; to eat openly at restaurants; to the millennium celebration in Times Square; and to Town Hall meetings.

"Judith Nathan is a very, very fine person," he said at that press conference. "And I’m going to need her more now than maybe I did before."

Ms Hanover called in the divorce lawyers, kicked him out of Gracie Mansion – the mayor's residence – and the tabloids went wild.

With Ms Nathan, a former nurse, came further excess.

He married her in May 2003: his third wedding was held at Gracie Mansion and was one of only two performed by mayor Michael Bloomberg. Among those attending was Mr Trump; when he married Melania two years later, Mr Giuliani would be there.

Mr Giuliani had tried to abolish term limits as mayor; when that failed, and he left City Hall, he set up a security consultancy and a law firm; wrote a book, Leadership; and struck out on the lucrative speaking circuit.

‘He’s a guy who really craves relevance and attention, and the media spotlight – and power really’ (Getty)

The son of a plumber and bartender, whose mother was a housewife, Mr Giuliani developed a taste for the high life. He used his worldwide speaking engagements to amass millions of dollars, six homes and 11 country-club memberships for the high-flying couple.  

They lived in a palatial $5m (£3.7m) nine-room Upper East Side apartment, described in Vanity Fair as having its dining room "walnut-panelled and crammed with crystal, china, and linen from (luxury department store) Scully Scully". The apartment had its own cigar room, complete with a bust of Winston Churchill, who Mr Giuliani liked to liken himself to.

His efforts to remain in the spotlight worked. At the end of 2006, Mr Giuliani was the most popular politician in the country: when, in March 2007, he formally announced his White House campaign, he was the early favourite to win the Republican primary contest, with 44 per cent of support nationwide.

John McCain, the eventual nominee, was second with 20 per cent. Mr Giuliani kept ahead of Mr McCain throughout the year, and raised the most money, campaigning on the slogan: “Tested. Ready. Now.”

He seemed destined to represent the Republican Party in the November 2008 election. But his lack of focus and preparation saw him come unstuck, coupled with an ill-conceived political plan of ignoring Iowa and New Hampshire and focusing on Florida, which ultimately rejected him.

After losing Florida, he threw in the towel. “Giuliani has a history of kind of overestimating his political appeal, and also over-reaching,” said Robert Polner, who covered Mr Giuliani’s mayoralty as a reporter for Newsday, and later edited a book on Giuliani: America’s Mayor, America’s President?  

“He’s a guy who really craves relevance and attention, and the media spotlight – and power really.” And so it was perhaps inevitable he would be drawn into Mr Trump's inner circle.

Returning to the spotlight after a decade, Mr Giuliani gave such a passionate defence of Mr Trump and denouncement of Hillary Clinton that people started questioning his sanity.

As the rats abandon the sinking Trump presidency, only set on saving themselves, Mr Trump and Mr Giuliani are sticking together

At first his role was advising him, during the campaign, on law and order policies. When Mr Trump wanted to institute a "complete and total shutdown" of Muslims entering the country, he turned to Mr Giuliani for advice on how to do it.

“When he first announced it, he said Muslim ban,” said Mr Giuliani, on Fox News. “He called me up, he said: ‘Put a commission together, show me the right way to do it legally.’”  

Mr Giuliani was openly angling for a job – perhaps attorney general, he modestly suggested. “There's probably nobody that knows the justice department better than me,” he told CNN the week after the election.

A month later, though, he had changed his tune. The media was poring over his work in the years after he left City Hall, and Mr Giuliani did not like it, so put himself out of contention.

He had said the role of secretary of state “was the only one I had any real interest in”; when that went to Rex Tillerson, Mr Giuliani said he was no longer keen to join the cabinet. Mr Trump instead made him a cybersecurity adviser, in January 2017.

Mr Giuliani, of course, made the role his own – enthusiastically embracing the idea that Barack Obama's administration spied on the Trump campaign, and diving in to Mr Trump's accusations that Mr Biden was corrupt and compromised by business dealings with his son, Hunter. He became Mr Trump's own private eye – trench coat optional. 

Rudy Giuliani contradicts himself on claimed meeting between Trump and Lev Parnas

It was Mr Giuliani who wined and dined two Ukrainians who said they had dirt on Hunter Biden. When Mr Trump set out to leverage the promise of a White House visit and millions in US assistance for Ukraine, in order to force Ukraine to investigate Mr Biden, it was Mr Giuliani who was his point-man.

Two of his associates, Lev Parnas and Igor Fruman, were arrested on suspicion of making illegal campaign contributions, and charged in October 2019. They are due to go on trial in the Southern District of New York in February, and the prospect of Mr Giuliani being swept up in a trial in the district he once led with such panache has shocked his former colleagues.

“He was like all of us. He's imperfect, but he was a very good and inspiring United States attorney who made major prosecutions,” said Paul Shechtman, a partner at law firm Bracewell LLP who worked under Mr Giuliani as a federal prosecutor, including as head of the office's appeals division.

He told CNN: “For those of us who worked for him, the fact that our old office is investigating him is a dark day.”

Alvin Bragg, another former prosecutor in the district, said that many of his cohort found Mr Giuliani's conduct startling, and sad.

“I think the biggest constant from the Southern District community has been, can you believe that Rudy Giuliani was ever US attorney? What an embarrassment,” he said. “I've heard that from several people. How repugnant and foolish his conduct has been.”

When, in the autumn of 2019, his third marriage fell apart, The New York Times headlined their story: “Giuliani Divorce: It’s Ugly, It’s Operatic. What Did You Expect?”

Their historic friendship is part of the reason why Trump allows him to stick around (Getty)

The pair fought in court over things as prosaic as her kitchen renovations and as rarefied as his splurges – $7,131 (£5,200) on fountain pens and another $12,012 (£8,800) on cigars.

“It is beyond me why either party in this case would have an interest in having all of this done publicly,” Justice Michael Katz said at an appearance last year in State Supreme Court in Manhattan. Settling privately, he advised, “would treat their relationship and marriage with more respect than divulging all our dirty laundry out for public consumption”. They did settle privately, in December 2019.

And then 2020 rolled around.

The Republican leadership always knew that legal challenges to the 3 November election were extremely likely, and so planned accordingly.

Mr Giuliani, officially Mr Trump's lawyer, was pointedly not part of those plans – instead it was tasked to Justin Clark, his deputy campaign chief, senior counsel and the only lawyer in a formal Trump campaign management role. Mr Clark had been working for several months to line up law firms ready for the expected fights, The Washington Post reported.  

David Bossie was supposed to lead the charge, until coronavirus put him out of action.

Yet Mr Giuliani and Mr Trump were not impressed with how the legal challenges were playing out. The feeling was mutual. Many of the other lawyers felt that Mr Giuliani seemed “deranged” and ill-prepared to litigate, a source told The Washington Post – that didn't stop him returning to court in Pennsylvania, appearing before a federal judge for the first time in almost 30 years.

He forgot the judge’s name, stumbled over the law and the facts, and called his opposing lawyer “that man who was angry at me”. He then needed the meaning of “opacity” explained to him by the judge.

The most dangerous place in New York is between Rudy and a microphone

There were no grudges, though: the judge ended by recommending Mr Giuliani, famously fond of a tipple, his favourite martini bars. It was blindingly obvious that Mr Giuliani and Jenna Ellis, his protegee, were “performing for an audience of one”.

Mr Trump held Mr Giuliani in high regard as “a fighter” and as “his peer”, the paper reported.

On 13 November, Mr Giuliani and Ms Ellis staged what a senior administration official called “a hostile takeover” of what remained of the Trump campaign.

Mr Trump called Mr Giuliani from the Oval Office while other advisers were present, including Mr Pence; White House counsel Pat Cipollone; Johnny McEntee, the director of presidential personnel; and Mr Clark, the deputy campaign manager who had laid the legal foundations for the challenges.

Mr Giuliani, on speakerphone, told the president that he could win and that his other advisers were lying to him about his chances. Mr Clark called Mr Giuliani “an expletive”, the paper reported, and said he was feeding the president bad information.

The following day, 14 November, Mr Trump tweeted that Mr Giuliani, Ms Ellis, Sidney Powell and others were now in charge of his legal strategy.  Ms Ellis arrived at the campaign’s Arlington headquarters and told employees that they must now listen to her and Mr Giuliani, the paper reported.

“They came in one day and were like, ‘We have the president’s direct order. Don’t take an order if it doesn’t come from us,’” a senior administration official recalled. Mr Clark and Jason Miller, an aide to the president, objected and so Ms Ellis threatened to call Mr Trump – to which Mr Miller replied: “Sure, let’s do this,” said a campaign adviser.

Rudy Giuliani appears to threaten Donald Trump on national television that he has 'insurance' in case he tries to throw him under the bus

Ultimately Mr Giuliani and Ms Ellis were victorious in taking control of Mr Trump’s legal strategy.

On 23 November the president reluctantly allowed the General Service Administration to approve the release of funds for the Biden transition team, and grant them permission to speak to government officials.

Permission was granted, however, after Mr Trump's aides told him that it didn't mean he had to give up his legal fight, or concede. Mr Trump and Mr Giuliani, after more than 30 years together, are not going to quit now. Even if their fight is increasingly ridiculous.

The strategy, according to a senior administration official, is: "Anyone who is willing to go out and say, ‘They stole it,’ roll them out. Rudy Giuliani, Jenna Ellis, Sidney Powell. Just roll everybody up who is willing to do it into a clown car, and when it’s time for a press conference, roll them out.”

So why does Mr Trump keep him around?

Part of it is their historic friendship; Mr Trump puts enormous value on loyalty. He knows that Mr Giuliani is all-in on the cause; he has thrown his lot in with the Trumps, and knows that this is his swansong. He is not working with one eye on his next act.

The president also reportedly considers Mr Giuliani a peer. He is someone he can talk freely to, and someone who feeds his ego, agrees with his theories. They are in their own comfortable echo chamber: it's them against the world.

Rudy Giuliani in Drag flirting with Donald Trump for the Mayors Inner Circle press roast

For both men, the personal and professional cost is inestimable.

“I got about five friends left,” Mr Giuliani was overheard telling a reporter for the New York Daily News, in what was embarrassingly termed "a butt dial". He thought he had hung up after their conversation, but his phone was still connected.

Caroline Giuliani, before the election wrote: “If being the daughter of a polarizing mayor who became the president’s personal bulldog has taught me anything, it is that corruption starts with ‘yes-men’ and women, the cronies who create an echo chamber of lies and subservience to maintain their proximity to power.”

After the election, she trolled her father with "self care" tips in Vanity Fair, including: “Avoid charcoal products or anything with artificial dyes, which may result in your face oozing as you make false claims of voter fraud in Philadelphia, for example.”

“Take stock of your failures,” she wrote. “Only sociopathic narcissists have delusions of grandeur, blaming others for their failings, often with tragic consequences.”  

Mr Giuliani was reported by The New York Times to have demanded $20,000 (£14,600) a day – a figure he insists was a lie. But even if he was paid $20,000 a day, would it be enough?

“If I could get him in in a candid moment where he'd really tell me what he thought, I'd ask him why he's doing this,” said Jeffrey Harris, who worked with Mr Giuliani while they were young attorneys in New York.  

Mr Giuliani was a junior federal prosecutor in the 1970s, and Mr Harris was the deputy associate attorney general, who told NPR that Mr Giuliani at the time was “among the very, very best – the top two or three”.  

“What's going to be the first paragraph in his obituary, if we sort of put it in those terms,” Mr Harris said. “I’d say to him: ‘Rudy, why did you take such an excellent career where you got accolades every step along the way, and associate yourself with these kinds of activities?

“Where, other than the hardcore Trump supporters, most people think you have become a joke.”

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