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Friends and foes of Rudy Giuliani ponder a similar question these days: is there method to the seeming madness of his defence of Donald Trump?
The debate has been raging since Mr Giuliani joined Mr Trump’s legal team last April and then embarked on a series of bewildering public appearances that, in legal terms, can charitably be described as unconventional.
One-time admirers wince each time he takes to cable television. Even longtime opponents express a kind of sadness at Mr Giuliani — the fearless prosecutor who took down the mafia, the commanding mayor who cleaned up a crime-ridden New York and the hero of 9/11 — becoming an object of ridicule in some quarters.
“I take no joy,” said Hank Sheinkopf, a Democratic political strategist who advised former president Bill Clinton, among others. “This is a guy who broke up the mafia! You’re talking about a serious, serious person . . . What he looks like now is a shell of himself talking gibberish.”
The president’s legal troubles appear to have entered a critical phase with the arrest on Friday of his longtime confidant Roger Stone for allegedly lying to congressional investigators probing Russia’s meddling in the US election. Mr Stone has denied wrongdoing and dismissed the investigation as a witch hunt.
As the pressure has intensified, Mr Giuliani’s response has startled veteran defence lawyers. Earlier this month he opened the door to possible collusion between the Trump campaign and Russia, telling CNN in a tetchy exchange: “I never said there was no collusion!” — denying only that the president was involved.
Then a few days later, he claimed Mr Trump had told him that negotiations to develop a Trump Tower in Moscow continued “from the day I announced [my campaign] to the day I won”.
That contradicted the Trump team’s longstanding insistence the talks had ended months earlier, drawing a clear a line between candidate Trump and the business ties to Russia that are a central focus of special counsel Robert Mueller. As jaws dropped, Mr Giuliani the next day tried to backtrack, calling his comments “hypothetical”.
Months earlier, he appeared to implicate his client in a campaign finance violation when he volunteered to Fox News’ Sean Hannity that Mr Trump had reimbursed his personal lawyer, Michael Cohen, for a $130,000 payment to adult film actress Stormy Daniels that, prosecutors say, was meant to buy her silence during the campaign.
Mr Giuliani even called the pay-off “a very regular thing for lawyers to do” — to the chagrin of Greenberg Traurig, the law firm that employed him until he joined the Trump defence.
He has also spoken, tantalizingly, of the existence of “tapes” that might prove Mr Trump’s innocence — before rowing back — and blasted FBI agents he once championed as “stormtroopers”.
“I just don’t see how what he’s doing is helping,” said Roland Riopelle, a New York criminal defence lawyer. The standard operating procedure for defence attorneys in such matters, he and others agreed, is to stick to the facts, avoid speculation and refrain from any statements that might antagonise prosecutors.
One school of thought is that Mr Giuliani is trying to soften the blow for any eventual legal findings against Mr Trump by first airing them on television — either to lessen their sting or purposefully muddy the waters. Having concluded that a sitting president cannot be indicted, this thinking goes, Mr Giuliani is not mounting a classic legal defence but instead putting up a political one — rallying Mr Trump’s supporters in the hope that their electoral support will help head off a possible impeachment.
Speaking to The New Yorker magazine, Mr Giuliani hinted at such a strategy, saying of Mr Trump’s case: “I thought legally it was getting defended very well. I thought publicly it was not getting defended very well.”
Even so, Mr Riopelle argued, Mr Giuliani had bungled the job by making so many conflicting statements that his own credibility was now shredded.
A long-serving city official quipped that a cunning Mr Giuliani was either trying to “make [Trump] look like the sane one” or “tie up the news cycle so they don’t report on other things”.
As Mr Giuliani, now in the midst of his third divorce, has appeared more erratic, whispers about his sessions at New York cigar bars have grown more insistent. Speaking to Politico last year, he denied imbibing before his media appearances or being anything more than a social drinker. “It’s extremely insulting,” he said. “There’s no proof at all that I take too much alcohol.”
Mr Giuliani did not return a call for comment.
Some dismiss claims over his drinking as reckless speculation. They focus instead on the possibility that Mr Trump, who is known to keep his own counsel, is hindering his lawyer by refusing to share all the details of his case.
“I always tell my clients: the last thing you need is a lawyer who doesn’t know all the facts. It can cause a lot of trouble,” said Michael Bachner, a New York defence lawyer and former prosecutor, adding: “I don’t believe he’s losing it . . . He’s a brilliant guy, a brilliant lawyer.”
But others disagree. One former colleague pointed to Mr Giuliani’s age — he is 74 — and suggested that after growing wealthy in the private sector he no longer had the same hunger and discipline. “He’s less sharp than he was,” this person said.
Like Mr Trump, Mr Giuliani was a young man who stormed Manhattan from the outer boroughs. He was renowned as a prosecutor for not only convicting Wall Street financiers such as Ivan Boesky and Michael Milken but marching prominent bankers in handcuffs in front of television cameras. The Republican mayor was revered for his mastery of facts and detail. He could speak for hours on the intricacies of the New York City budget without notes.
What many fail to appreciate beyond New York is that his domineering approach and desperation for the limelight had deflated his popularity in the pre-September 11 world. Stunts such as informing his second wife of their divorce via a public news conference had long since prompted many New Yorkers to question his empathy and judgment.
Had there been an election on September 10 2001, Mr Sheinkopf said, Mr Giuliani would have been trounced. It was his galvanising response to the terrorist attacks that revived his reputation at home and made him a hero around the world.
“He couldn’t walk into a restaurant without people giving him a standing ovation,” recalled Andrew Kirtzman, author of the book Rudy Giuliani: Emperor of the City.
Since then, Mr Kirtzman and others argue, Mr Giuliani’s existence has been at times a desperate — but also well-paid — struggle to regain those heights and that sense of relevance.
While a 2008 presidential run fizzled out, Mr Giuliani focused his energy on the private sector. He had opened his own consultancy, Giuliani Security & Safety, in 2002, advising companies and governments on issues such as cyber security and crisis management.
He also enjoyed a decade-long partnership with Bracewell, the Houston law firm, before jumping to Greenberg in 2016 along with Marc Mukasey, a fellow former prosecutor. His consulting work has brought adulation and fees from high-paying clients around the world — although sometimes in less savoury locales such as Bahrain, Congo and Romania.
As Mr Trump’s outsider presidential campaign gained speed, Mr Giuliani found a way back from the wilderness. He took to cable news as a surrogate to defend his old friend, standing by him even when an old tape emerged of Mr Trump speaking in vulgar terms about groping women. The two have much in common: they are irascible, larger-than-life, thrice-married New Yorkers of a certain generation.
The culmination of Mr Giuliani’s campaigning was a thundercloud of a speech at the Republican National Convention in which he warned of the dark forces stalking the US and the danger of a Hillary Clinton presidency.
“Hillary Clinton is for open borders,” Mr Giuliani declared. “She is in favour of taking in Syrian refugees even though the Islamic State has told us they are going to put their operatives in these groups so they can carry out terrorist acts against us and our allies.”
After Mr Trump’s improbable victory, Mr Giuliani’s name surfaced as a possible secretary of state. In his book Fire & Fury: Inside the Trump White House, Michael Wolff wrote that the president-elect wanted to reward him but ultimately faced opposition from his team amid “whispers from the staff ‘about his health and stability’”. (In a 2007 Vanity Fair profile, Mr Wolff rendered his own judgment of Mr Giuliani: “He is nuts, actually mad.”)
Since joining the president’s legal team Mr Giuliani has made his way into the middle of the world’s biggest drama — a story that plays out around the clock on cable television and social media. “It’s irresistible for Rudy at this stage of his life,” the former colleague said. “This is his Icarus moment. He’s drawn to the flame of public attention.”
It remains to be seen for how long he will hold the spotlight. There have been conflicting reports in recent days that some administration officials are determined to muzzle Mr Giuliani. In the meantime, observers are left to debate whether his recent antics are part of a grand strategy and to puzzle over what has become of the man once celebrated as “America’s Mayor”.
Mr Kirtzman said: “His heroics on September 11th now seem very far away.”
