The former mayors theatrical, combative style of politics anticipatedand perfectly aligns withthe Presidents.
Giuliani, like the President, is not seeking converts but comforting the converted.
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 Havanas 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 windgood for the golf course, he told me. He drew his first puffs and placed an even larger stogiea gift from his thirty-two-year-old son, Andrew, who works in the White House Office of Public Liaisonon 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 Giulianis 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 didnt 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 incarnationas an intimate of, and a defense attorney for, the President of the United States. In 2007, the family business of Jared Kushner, Donald Trumps 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 Kushners plans to salvage the investment involved tearing down the building and displacing the Grand Havana. I always tell Jared Im rooting against him, Giuliani told me, chuckling. Theres nowhere else in the city that wants hundreds of cigar smokers. (Kushners family recently received a financial lifeline from a real-estate investment firm, and current plans call for the club to remain.)