Rudy Giuliani was once warmly embraced by New York’s glamorous Upper East Side, mingling with press and public at upscale neighborhood haunts.
He was a regular at Tony’s Di Napoli, a huge Italian restaurant just minutes from his apartment. Twenty years ago, he was mobbed by journalists while driving his mistress home after dinner.
Mention of Mr. Giuliani now elicits blank stares and sneers from wait staff who are normally happy to mention the names of celebrity regulars.
A waiter nodded at the mention of the former New York mayor. “Giuliani?” he laughed and walked away. “I don’t like him.”
The reaction would have been unthinkable even a few years ago. Mr. Giuliani burnished his reputation in the city by taking on the mob as a U.S. attorney, tackling rising crime rates as mayor and running for the World Trade Center when the first plane hit on Sept. 11, 2001.
Today he is an 80-year-old bankrupt facing potential prison time in two criminal cases.
Desperately strapped for cash, the man leaves the city where he has built a reputation for decades.
At The Mansion, the Upper East Side restaurant known for its large portions and extensive menu, Mr. Giuliani has not been seen in nearly five years. He often dined there with his son Andrew.
The mansion’s walls are covered with photos of famous visitors such as former president George W. Bush, New York congresswoman Alexandria Ocasio-Cortez and her successor as mayor, Michael Bloomberg. A picture of Mr. Giuliani is conspicuously absent.
He was forced to declare bankruptcy in December 2023 after losing a defamation case and was reprimanded by the judge in May 2024 for his spending habits.
America’s Mayor is now the brand of coffee
Mr. Giuliani, who led Donald Trump’s legal efforts to overturn the results of the 2020 presidential election, was recently served with a subpoena in a second election interference case.
He was known as “America’s Mayor” for leading New York and the rest of the country in the wake of 9/11. Now America’s Mayor is a coffee brand he bought for $30 (£24) a bag.
Ken Frydman, the press secretary for Mr. Giuliani’s successful 1993 mayoral campaign, was appalled that a man he admired had become a “QVC-style” coffee salesman.
He believes his former boss hasn’t reached the bottom yet. “If Rudy is convicted, sentenced and jailed, that will be the end,” he told The Telegraph. “From America’s Mayor to America’s Prisoner.”
Mr. Giuliani, who already faces criminal charges in an election interference case in Georgia, pleaded not guilty this week in a similar case in Arizona.
Prosecutors apparently had a hard time finding him to serve the subpoena while he taunted them on social media. They finally caught him leaving his birthday party in Palm Beach, Florida.
He declared bankruptcy in December 2023 after being found liable for $148 million after defaming two 2020 election workers.
The judge in the bankruptcy case said in May that he was “troubled” that Mr. Giuliani had done so little to fix his financial situation, which had conspicuously exceeded his $43,000 monthly budget. His lawyer claimed that no accountant would approach him.
His name was also mentioned repeatedly at Donald Trump’s “hush money” hearing in New York, allegedly as part of a pressure campaign against Mr Trump’s former “fixer” Michael Cohen.
New Yorkers, who lined up front row outside Manhattan Criminal Court for Mr. Trump’s blockbuster trial, were horrified at what had happened to the former 9/11 hero.
One member of the public predicted that he would “die broke and in prison.” Another said he could have stayed out of the political struggle, adding: “All he had to do was do nothing.”
Turning in the apartment in Manhattan
Mr. Giuliani is now surrendering his three-bedroom Manhattan apartment to creditors, putting it up for sale this month for $5.7 million.
A few days ago, he was fired from his job as a New York radio host after claiming that the 2020 election was rigged by Joe Biden. He now plans to move to Palm Beach to continue his podcasting career.
This marks his final break with the city for which he became famous. As U.S. attorney for the Southern District in the 1980s, he dealt a stunning blow to organized crime by securing the convictions of top mob figures, and in the 1990s, while in city hall, he greatly reduced crime.
Another of his coffee brands, “Fight for Justice,” references his career as a crime fighter. The packaging features noire-style images of a young Mr. Giuliani, as well as gangsters and the New York skyline
“He was probably the most effective mayor in the history of the city,” Mr. Frydman reflects.
When he meets people who remember Mr. Giuliani only as Trump’s lawyer, “he has to tell them that he was the one who changed the city.”
He added: “He destroyed his own legacy through self-inflicted wounds. “This is a self-inflicted tragedy.”