As President Donald Trump and White House aides expressed their discomfort over Rudy Giuliani’s free-wheeling interviews, those who know the former mayor from his native New York City and who’ve seen him at recent events suggest it’s just Rudy being Rudy.

They described a man whose once-powerful legal career long ago morphed into a role of attracting clients for law firms and using his contacts to help emerging businesses. Much of that work was conducted in loose social settings, with Giuliani drawing attention for his outrageous statements — frequently directed at his favorite target, Hillary Clinton — while delighting some listeners and offending others.


On Tuesday, however, MSNBC’s Joe Scarborough went so far as to state on live television that Trump didn’t initially hire Giuliani for a Cabinet post because he was “losing it,” “falling asleep five minutes into meetings” and “drinking too much” — charges that Giuliani himself rejected in his own combative style in an interview with POLITICO.

“None of that is true,” Giuliani said of Scarborough’s remarks in an interview Tuesday afternoon. “I’m not sleeping now. I’m in Dallas. I’m wide awake. I’ve handled numerous cases including some sensitive cyber matters. I’m a lot more aware and intelligent than Joe has ever been and a lot more accomplished. Joe hasn’t been knighted by the Queen of England. He hasn’t run a U.S. attorney’s office, much less a city that he turned around or went through 9/11.”

As for the allegations about his drinking, Giuliani acknowledged being a social drinker but said he doesn’t have alcohol early in the day.

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“I’m not drinking for lunch,” he said. “I may have a drink for dinner. I like to drink with cigars.”

Giuliani’s conduct since joining the Trump legal team has been the subject of several private conversations in recent weeks among current and former Trump advisers and attorneys involved in the Russia investigation who have been asking one another about the lawyer’s drinking and other erratic behavior. The concern: whether it’s causing more problems for a president who already had a pile of legal and political problems. Many say they’ve been reassured there’s nothing to be worried about.

“Rudy does have pretty good political instincts, but no one hits a home run every time they’re at the plate,” said Barry Bennett, a former Trump campaign aide. “I don’t think drinking is an issue.”

Several Giuliani friends noted that much of his business is conducted in settings in which drinks are served, and that Giuliani’s flamboyant personality only gets more colorful when he imbibes.

In New York, a favorite hangout is the Grand Havana Room at 666 Fifth Ave., where he is frequently seen in the evening puffing cigars with friends like defense attorney and law-firm partner Marc Mukasey. Two New York political insiders familiar with Giuliani’s activities said he was at the Grand Havana before his now-infamous Fox News interview with Sean Hannity, in which he shocked much of Washington by blurting out that Trump had known after all about Michael Cohen’s payoff to porn star Stormy Daniels — something the president had denied.

Giuliani said he thinks he was at the Grand Havana after his Hannity interview but couldn’t remember the specifics. “I sometimes go before,” he said. “I sometimes go after.”

A person familiar with the interview said Hannity didn’t smell alcohol on Giuliani’s breath or otherwise notice that the Trump lawyer had been drinking. Giuliani also dismissed the question of whether he’d had any alcohol before going on Hannity’s program. “I’m insulted,” he said. “It’s extremely insulting. There’s no proof of any kind that I take too much alcohol. That’s ridiculous.”

In Washington, Giuliani also has some favorite hangouts. He’s been spotted at Shelly’s Back Room cigar bar on F Street, a plush setting two blocks from the White House with wood paneling and leather armchairs.

From his favorite bars he sometimes moves on to social events, as his workday morphs into his evening. There, the colorful former mayor often entertains listeners with his tart observations on the political scene.

In March, Giuliani reportedly raised eyebrows at Mar-a-Lago when, in a room full of wealthy Republicans including the president, he joked about having seen Hillary Clinton at Trump’s wedding and “she actually fit through the door.” According to Axios, which reported the event, the fat joke drew a foul look from his wife, Judith — who last month filed for a contested divorce — while Trump later quipped to the crowd that he was glad he didn’t say it.

Jon Sale, a former federal prosecutor and law school classmate of Giuliani’s, said his friend knew how to maintain control of a situation. “I’ve never seen him impaired. Anybody who says he has a drinking problem doesn’t know him or has an agenda,” Sale said.

For his part, Giuliani insisted it’d be big news in his hometown if drinking were an issue. “You’d have 50 gossip columns on Page Six with the scrutiny I get in New York,” he said.

The White House did not respond to a request for comment about Giuliani’s behavior — which also drew notice on MSNBC last Friday when host Chris Matthews suggested that the Trump lawyer’s interview with Hannity was a misstep.

“Would you go on national television after dinner? I worked in the House, where these guys all got in trouble. You know what I’m saying. Wine is served in the House dining room. And they go on and have to go back and take the words down,” Matthews said. “Don’t go to dinner first if you’re going on national television.”

In the wake of POLITICO’s report on Monday that Trump was angry about Giuliani’s performance as the public face of his legal team, some former associates note that the president, who has known Giuliani for decades, is as familiar as anyone with the former mayor’s ad-hoc style, and that he must have decided that it’s what was needed on his defense team.

“So if he’s doing the New York thing of hanging out in the late afternoon and having some drinks, that isn’t unusual,” said veteran New York political operative Hank Sheinkopf, referring to Giuliani. “What is unusual is people trying to find an explanation for Giuliani’s historic behavior, which is off-the-cuff and very ballistic. His basic style hasn’t changed since the day he was elected mayor [in 1993]. Why should he change? It worked.”

Yet critics who have observed Giuliani over the years say he appears less sharp than he was as mayor, if every bit as outrageous.

“The serious issue here is that Rudy Giuliani, at least during the national convention speech and watching him on TV through the fall, seems like he’s lost more than one card in the deck,” said Lanny Davis, a Washington lawyer who helped manage the Clinton White House’s response to independent counsel Kenneth Starr’s investigation.

“They should change his name to Rusty Giuliani,” quipped Sol Wisenberg, a former deputy counsel on Starr’s prosecutorial team. “He’s rusty on the law, he’s rusty on the facts.”

Giuliani told POLITICO that his early forays on television as Trump’s lawyer — to defend the president on the Daniels payments — had forced him to sideline his attempts to get up to speed on the Mueller case. He has since shifted back to the Russia probe and going forward plans to continue doing media interviews only “selectively, and when we want to set the agenda.”

“It’s far better that I draw the fire than the president,” Giuliani said. “That’s what a lawyer is for. Some lawyers don’t think so. I think he’s very comfortable now that someone is doing that for him.”

Trump’s allies initially heralded Giuliani’s arrival last month as a big-name attorney who could help bring order to a personal legal team short-handed after the resignation of John Dowd. Former Trump campaign manager Steve Bannon called Giuliani and Emmet Flood, who was hired last week as a new White House attorney on the Russia case to replace Ty Cobb, the president’s “wartime consiglieres.”

Several sources also spoke about Giuliani’s loyalty to Trump during perhaps his worst moment of the 2016 campaign: the release of the “Access Hollywood” tape, in which the Republican can be heard bragging about sexual assault. While many Trump surrogates abandoned their presidential nominee, Giuliani agreed to defend Trump on multiple national television programs.

“That’s the type of man Rudy Giuliani is,” said former Trump campaign manager Corey Lewandowski.

After Trump’s election, Giuliani wanted to be appointed secretary of state, according to several of his friends. But Trump passed him over for the diplomatic job. Giuliani’s friends say he didn’t want to return to law enforcement and took his name out of consideration to head the Justice Department or Homeland Security to remain at the law firm Greenberg Traurig — though he has since taken a leave of absence from the firm’s New York office for the assignment as Trump’s most prominent personal lawyer.

But the reaction to Giuliani’s time on television since taking the Trump lawyer job has been a mixed bag. He’s certainly helped the president dominate the national conversation, but the president has griped to associates that Giuliani has failed to shutter the Daniels saga and his media appearances keep raising more questions.

“I think there’s a master strategy at play here,” said a former Giuliani colleague. “But whether it’s a legal strategy is an open question.”

Eliana Johnson contributed to this report.

