Mr. Giuliani’s ex-wife Judith, who was with him at the time, told me that what gnawed at the former mayor most was a creeping fear of irrelevancy. (The couple divorced in 2019.) The flameout forced him to lower his sights from how to amass power to how to hold on to what he had left. When he offered a reporter a rare post-mortem on the race in 2009 he betrayed his concern. “I think I should’ve fought Iowa harder,” he told New York magazine. “That was the beginning of becoming irrelevant.”
After endorsing John McCain at the end of January, Mr. Giuliani disappeared from public view. Eager to escape the dreary cold of February in New York, he and his wife packed their bags and went to Florida to stay at her parents’ two-bedroom condo in Palm Beach, which Mr. Giuliani bought for them. They lived in Palm Beach Towers, an upscale high-rise apartment complex, with views of the crystalline blue Intracoastal Waterway, a swimming pool, landscaped gardens and nearby golf courses — a natural place to relax after a brutal campaign. But he rarely left the apartment, spending his time sitting listlessly on his in-laws’ living room couch, sleeping late in the bedroom or smoking cigars in his bathrobe on the terrace facing a parking lot.
Ms. Giuliani said he refused to socialize or sit for meals, even as her mother, Joan, tried to entice him with his favorite dish, pasticcio. “It started to really worry me because he was waking up only if I would wake him,” she said. He became melancholy and self-pitying (“You should leave me”), she said. Her response — “You still have kids that love you, you have me, you have your health” — failed to assuage his sense of failure. “He just could not get over it,” she said.
She said he started to drink more heavily. While Mr. Giuliani was always fond of downing a scotch with his cigars, his friends never considered him a problem drinker. Ms. Giuliani felt he was drinking to dull the pain. The situation was concerning enough to send the couple searching for a more discreet locale for his recuperation, as the press caught on to their stay at Palm Beach Towers and photographers started popping up.
In search of a friend to turn to, they found one in Donald Trump. “We moved into Mar-a-Lago and Donald kept our secret,” Ms. Giuliani said.
Mr. Trump provided them with a hideaway that was secluded from the press and passers-by, a safe space for an ailing friend who was a magnet for photographers. He had a perfect spot for them — a bungalow across the street from Mar-a-Lago. A small tunnel ran underneath South Ocean Boulevard, a narrow two-lane highway, allowing the Giulianis to walk to dinner beyond the glare of the press. “He thought he was finished,” she told me. His drinking accelerated, she said, the beginning of a series of episodes in which he fell and hurt himself. “He was always falling shitfaced somewhere,” she said.