Rudy Giuliani had always been hard to miss at the Grand Havana Room, a magnet for well-wishers and hangers-on at the midtown Manhattan cigar club that still treated him like the king of New York.
In recent years, many close to him feared, he was becoming even harder to miss.
For more than a decade, friends conceded, Giuliani’s drinking had been a problem. And as he surged back to prominence during the presidency of Donald Trump, it was getting more difficult to hide it.
On some nights when Giuliani was overserved, an associate discreetly signaled the rest of the club, tipping back his empty hand in a drinking motion, out of the former mayor’s line of sight, in case others preferred to keep their distance. Some allies, watching Giuliani down Scotch before leaving for Fox News interviews, would slip away to find a television, clenching through his rickety defenses of Trump.
Even at less rollicking venues — a book party, a Sept. 11 anniversary dinner, an intimate gathering at Giuliani’s own apartment — his consistent, conspicuous intoxication often startled his company.
“It’s no secret, nor do I do him any favors if I don’t mention that problem, because he has it,” said Andrew Stein, a former New York City Council president who has known Giuliani for decades. “It’s actually one of the saddest things I can think about in politics.”
No one close to Giuliani, 79, has suggested that drinking could excuse or explain away his present legal and personal disrepair. He arrived for a mug shot in Georgia in August not over rowdy nightlife behavior or reckless cable interviews but for allegedly abusing the laws he defended aggressively as a federal prosecutor, subverting the democracy of a nation that once lionized him.
Now, prosecutors in the federal election case against Trump have shown an interest in the drinking habits of Giuliani — and whether the former president ignored what his aides described as the plain inebriation of the former mayor referred to in court documents as “Co-Conspirator 1.”
The office of the special counsel, Jack Smith, has questioned witnesses about Giuliani’s alcohol consumption as he was advising Trump, including on election night, according to a person familiar with the matter. Smith’s investigators have also asked about Trump’s level of awareness of his lawyer’s drinking as they worked to overturn the election and prevent Joe Biden from being certified as the 2020 winner at almost any cost. (A spokesperson for the special counsel declined to comment.)
The answers could complicate any efforts by Trump’s team to lean on a so-called advice-of-counsel defense, a strategy that could portray him as a client merely taking professional cues from his lawyers. If such guidance came from someone whom Trump knew to be compromised by alcohol, especially when many others told Trump definitively that he had lost, his argument could weaken.
In interviews and in testimony to Congress, several people at the White House on election night — the evening when Giuliani urged Trump to declare victory despite the results — have said that the former mayor appeared to be drunk, slurring and carrying an odor of alcohol.
“The mayor was definitely intoxicated,” Jason Miller, a top Trump adviser and a veteran of Giuliani’s 2008 presidential campaign, told the congressional committee investigating the Jan. 6 attack on the Capitol in a deposition early last year. “But I do not know his level of intoxication when he spoke with the president.” (Giuliani denied this account.)
Giuliani faces a racketeering charge (among others) in Georgia, a defamation case brought by two election workers and accusations of sexual misconduct from a former employee (he has said this was a consensual relationship) and a former White House aide (he has denied this account).
One of his lawyers has said Giuliani is “close to broke.” Another, Robert Costello, is suing him for unpaid legal fees.
Giuliani’s circle has shrunk as old friends have fallen away. His law license was suspended in New York. The Grand Havana Room closed in 2020.
Most days, Giuliani hosts a radio show in Manhattan, stopping for sidewalk selfies with the occasional stranger.
Most nights, he stays in for a livestream from the apartment he long shared with his third ex-wife, Judith Giuliani. It recently went up for sale.
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