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 irrelevance. (The couple divorced in 2019.) The outburst forced him to lower his gaze from how to amass power to how to hold on to what he had left. When he offered a reporter a rare autopsy during the race in 2009, he betrayed his concern. “I think I should have fought harder against Iowa,” he told New York magazine. “That was the beginning to become irrelevant.”
After he approved John McCain in late January, Mr. Giuliani disappeared from view. Eager to escape the gloomy February cold in New York, he and his wife packed their bags and headed to Florida to stay at her parents’ two-bedroom apartment in Palm Beach that Mr. Giuliani had bought for them. They lived in Palm Beach Towers, a luxury high-rise apartment complex, overlooking the crystal clear 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 listlessly on the couch in his in-laws’ living room, sleeping late in the bedroom or smoking cigars in his bathrobe on the patio overlooking a parking lot.
Ms. Giuliani said he refused to socialize or eat, even when her mother, Joan, tried to tempt him with his favorite dish, pasticcio. “It really started to worry me because he only woke up if I woke him up,” she said. He became melancholy and self-pity (“You should leave me”), she said. Her response – “You still have children who love you, you have me, you have your health” – couldn’t take away his sense of failure. “He just couldn’t get over it,” she said.
She said he started drinking more heavily. While Mr. Giuliani always liked to drink a whiskey with his cigars, his friends never saw him as a problem drinker. Mrs. Giuliani felt that he was drinking to numb the pain. The situation was worrisome enough to send the couple looking for a more discreet spot for his recovery, as the press misunderstood their stay at Palm Beach Towers and photographers began to crop up.
Looking for a friend to go to, they found one in Donald Trump. “We moved to Mar-a-Lago and Donald kept our secret,” said Ms. Giuliani.
Mr. Trump provided them with a shelter secluded from the press and passers-by, a safe haven for an ailing friend who was a magnet for photographers. He had a perfect place for them: a bungalow across the street from Mar-a-Lago. A small tunnel ran under South Ocean Boulevard, a narrow two-lane highway, allowing the Giulianis to walk to dinner outside the glare of the press. “He thought he was done,” she told me. His drinking accelerated, she said, beginning a series of episodes in which he fell and injured himself. “He always fell into shit somewhere,” she said.
