Although it has been almost a generation since Rudolph Giuliani was the mayor of New York, there is one place in the city where he still presides: the Grand Havana Room, a tatty cigar club that occupies the top floor of 666 Fifth Avenue. Giuliani is on the Grand Havana’s board of directors and is a regular presence at the club. The room is filled with overstuffed armchairs, oversized ash trays, and the persistent haze of smoke. Thick velvet drapes, many the worse for wear, block out the view of the city, and ventilation machines wheeze from the ceiling. One afternoon this summer, Giuliani sank into a chair, pulled the knot of his tie down to his chest, and removed a Padrón fiftieth-anniversary cigar (retail price: forty dollars) from a carrying case. At seventy-four, Giuliani often seems weary. He limps. He has surrendered his comb-over to full-on baldness, and, as his torso has thickened, his neck has disappeared. He lit the Padrón with a high-tech flame lighter. “It works in the wind—good for the golf course,” he told me. He drew his first puffs and placed an even larger stogie—a gift from his thirty-two-year-old son, Andrew, who works in the White House Office of Public Liaison—on a cocktail table in front of him. “Andrew got it when he was playing golf with the President this weekend,” Giuliani explained.

Cigars have played a recurring role in Giuliani’s career. When he joined the Grand Havana, the club was struggling to find members. In 2002, his successor as mayor, Michael Bloomberg, banned smoking in restaurants and bars. “Mike didn’t realize it, but he saved us,” Giuliani said. “It became the only place you could smoke.” Giuliani met his third wife, Judith Nathan, at another cigar venue, Club Macanudo. (The couple are now divorcing.) The Grand Havana has also been a point of good-natured contention for Giuliani in his latest incarnation—as an intimate of, and a defense attorney for, the President of the United States. In 2007, the family business of Jared Kushner, Donald Trump’s son-in-law, paid $1.8 billion for 666 Fifth Avenue, which promptly fell dramatically in value, imperilling the Kushner real-estate empire. One of Kushner’s plans to salvage the investment involved tearing down the building and displacing the Grand Havana. “I always tell Jared I’m rooting against him,” Giuliani told me, chuckling. “There’s nowhere else in the city that wants hundreds of cigar smokers.” (Kushner’s family recently received a financial lifeline from a real-estate investment firm, and current plans call for the club to remain.)

The actor Alec Baldwin, another Grand Havana board member, described the club to me as “Republican Manhattan—Wall Street guys, Yankees fans, Rudy’s people.” On the afternoon I met Giuliani there, members stopped by periodically to pay respects. He reflected on the tumultuous six months he has spent thus far representing Trump in the investigation led by Robert Mueller, the special counsel. Giuliani’s work has involved countless television appearances—often featuring false or misleading claims—as well as frequent phone calls with the President and months of negotiations with Mueller about the possibility of Trump testifying. In all, he had a favorable estimation of his own performance. “I enjoy being a lawyer more than I do being a politician,” he told me. “As a politician, a lot of people are better than me. This is what I think I do best.”

The addition of Giuliani to Trump’s legal team has been part of a larger change in the President’s strategy. During the first year of the Mueller investigation, which began in May of 2017, John Dowd and Ty Cobb, the lawyers leading Trump’s defense, took a coöperative approach, turning over as many as 1.4 million documents and allowing White House staffers to be interviewed. Their public comments were courteous, even respectful. But, just as the cautious and deliberate style of Rex Tillerson, Trump’s first Secretary of State, and H. R. McMaster, Trump’s former national-security adviser, eventually frustrated the President, so, too, did that of Trump’s legal team. Trump wanted a more combative approach. Giuliani told me, of the early defense, “I thought legally it was getting defended very well. I thought publicly it was not getting defended very well.”

Since joining Trump’s team, Giuliani has greeted every new development as a vindication, even when he’s had to bend and warp the evidence in front of him. Like Trump, he characterizes the Mueller probe as a “witch hunt” and the prosecutors as “thugs.” He has, in effect, become the legal auxiliary to Trump’s Twitter feed, peddling the same chaotic mixture of non sequiturs, exaggerations, half-truths, and falsehoods. Giuliani, like the President, is not seeking converts but comforting the converted.

This has come at considerable cost to his reputation. As a prosecutor, Giuliani was the sheriff of Wall Street and the bane of organized crime. As mayor, he was the law-and-order leader who kicked “squeegee men” off the streets of New York. Now he’s a talking head spouting nonsense on cable news. But this version of Giuliani isn’t new; Trump has merely tapped into tendencies that have been evident all along. Trump learned about law and politics from his mentor Roy Cohn, the notorious sidekick to Joseph McCarthy who, as a lawyer in New York, became a legendary brawler and used the media to bash adversaries. In the early months of his Presidency, as Mueller’s investigation was getting under way, Trump is said to have raged, “Where’s my Roy Cohn?” In Giuliani, the President has found him.

Giuliani can’t remember the first time he met Trump, but he recalls taking special notice of him in 1986. Ed Koch was mayor, and Giuliani, who was the U.S. Attorney for the Southern District of New York, in Manhattan, was planning his own mayoral run. For years, the city had been trying, without success, to renovate the Wollman skating rink, in Central Park. Trump volunteered to complete the project in just four months, at a lower price than the city was proposing to pay. “He embarrassed Koch,” Giuliani told me. After the project was finished, he said, “Young Donald says, ‘I want it named after me.’ Koch goes nuts. Koch must have felt he was blindsided, thought it was arrogant, and he said no. And then Trump got on the warpath against him.” Giuliani said that, as his campaign to become the Republican mayoral candidate kicked into gear, Trump “became a very big supporter of mine.” In the end, Koch didn’t win the primaries in 1989, and Giuliani lost that year to David Dinkins, whom he defeated four years later.

Naked aggression and a thirst for attention have been hallmarks of Giuliani’s career. As U.S. Attorney, he won plaudits for prosecuting insider trading on Wall Street and for his relentless pursuit of the Mafia. He racked up more than four thousand convictions, including those of Ivan Boesky and of four of the five heads of the New York Mafia families. But he was also criticized for his practice of “perp walking”—marching white-collar criminals, in handcuffs, through the financial district, often in front of reporters who had been alerted in advance. He sometimes arrested people in their workplaces and then dropped the charges, seemingly as a way to intimidate them and send a message to associates. He drew ridicule for donning a leather jacket to make a supposedly undercover drug purchase in Washington Heights.