by Rudy Giuliani was once ensconced on New York’s glamorous Upper East Side, mingling with both the press and the public in his upmarket neighborhood.
He was a regular at Tony’s Di Napoli, a terrible Italian restaurant just minutes from his apartment. Twenty years ago he was swarmed by reporters as he walked his master home from a meal there.
References to Mr. Giuliani now draw white stares and quizzical looks from the wait staff, who are otherwise happy to name their celebrities.
A waiter shook his head at the former New York mayor. “Giuliani?” he laughed and walked away. “I do not like it.”
The reaction would have been unimaginable even a few years ago. Mr. Giuliani lost his reputation in the city, taking on the mafia as US attorney, tackling spiraling crime rates as mayor and racing for the World Trade Center when the first plane hit it on September 11, 2001.
Today he is an 80-year-old bankrupt with possible prison time for two criminal cases.
He’s short on cash, and he’s leaving the city where he built his reputation over the years.
At the Mansion, an Upper East Side restaurant known for its large portions and extensive menu, Mr. Giuliani has not been seen for about five years. He often dined there with his son Andrew.
The walls of the mansion are filled with photos of famous visitors including George W Bush, the former president, New York congresswoman Alexandria Ocasio-Cortez and Michael Bloomberg, his successor as mayor. Mr. Giuliani’s picture is conspicuously absent.
He was forced to declare bankruptcy in December 2023 after losing a defamation case, and a judge scolded him about his spending habits in May 2024.
Mayor of America is now a coffee brand
After spearheading Donald Trump’s legal efforts to overturn the results of the 2020 presidential election, Mr. Giuliani was recently served with a subpoena in his second election interference case.
He was dubbed “America’s Mayor” for leading New York – and the rest of the nation – through the aftermath of 9/11. America’s Mayor is now a coffee brand fronted by a $30 (£24) bag.
Ken Frydman, press secretary for Mr. Giuliani’s successful 1993 mayoral campaign, was horrified by the decline of a man he admired as a “QVC-style” coffee vendor.
According to him, his former boss has not arrived yet. “Rudy would be devastated if he was convicted, sentenced and jailed,” he told the Telegraph. “From America’s Mayor to America’s Criminal.”
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 trouble getting him to serve a court summons as he taunted them on social media. They eventually confronted him as he was leaving his birthday party in Palm Beach, Florida.
In December 2023 he declared bankruptcy after being found liable for $148 million after defaming two 2020 election workers.
The judge in his bankruptcy case in May said he was “disturbed” that Mr. Giuliani, after spending too much on his $43,000-a-month budget, had done little to fix his finances. His lawyer advised that no accountant should go near him.
His name was also repeatedly mentioned at Donald Trump’s “hush money” trial in New York, allegedly as part of a pressure campaign against former “fixer”, Michael Cohen.
New Yorkers queuing outside Manhattan Criminal Court for a front-row seat to Mr Trump’s high-profile trial over what happened to the former 9/11 hero were disappointed.
One member of the community predicted that he would die broke and in prison. Another said he could have stayed above the political scene, adding: “He just had to do nothing.”
Manhattan apartment to give up
Mr. Giuliani is giving up his three-bedroom Manhattan apartment to his creditors, putting it on the market for $5.7 million this month.
A few days earlier, he was fired from his job as a radio host in New York after he claimed that the 2020 election was rigged by Joe Biden. He now plans to move to Palm Beach to continue his podcasting career.
It marks his final break with the city where he rose to fame. He dealt a major blow to organized crime as US attorney for the southern district in the 1980s by securing convictions for senior mafia figures, and he greatly reduced crime while in city hall in the 1990s.
Another of his coffee brands, “Fighting for Justice”, refers to his career as a crime fighter. The packaging shows a young Mr Giuliani alongside noire-style images of mobsters and the New York skyline
“He was probably the most effective mayor in the history of the city,” Mr Frydman believes.
When he meets people who only remember Mr Giuliani as Trump’s lawyer he is “forced to tell them he was the man who turned the city around”.
He added: “He destroyed his own legacy with self-inflicted wounds. That is a self-inflicted tragedy.”
