Rudy Giuliani was once warmly embraced on New York’s glamorous Upper East Side, mingling with press and public alike in its upmarket neighbourhood haunts.

He was a regular at Tony’s Di Napoli, a cavernous Italian restaurant just a few minutes from his apartment. Twenty years ago he was swarmed by reporters as he walked his mistress home from a meal there.

Now mentions of Mr Giuliani draw blank stares and quizzical looks from its waiting staff, who are otherwise happy to name-drop their celebrity regulars.

A waiter shook his head at a mention of the former New York mayor. “Giuliani?” he laughed and walked off. “I don’t like him.”

The reaction would have been unthinkable even a few years ago. Mr Giuliani burnished his reputation in the city, taking on the mafia as US attorney, tackling spiralling crime rates as mayor and racing for the World Trade Center when it was hit by the first plane on Sept 11 2001.

Today he is a bankrupt 80-year-old who faces potential jail time from two criminal cases.

Desperately short of cash, he is leaving the city where he built his reputation over decades.

At The Mansion, an Upper East side diner known for its big portions and expansive menu, Mr Giuliani has not been seen for about five years. He used to eat there often with his son Andrew.

The Mansion’s walls are filled with photographs 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 was scolded by a judge about his spending habits in May 2024.

America’s Mayor is now brand of coffee

Having led Donald Trump’s legal efforts to overturn the results of the 2020 presidential election, Mr Giuliani was recently served with a court summons in a second election interference case.

He was known as “America’s Mayor” for steering New York – and the rest of the nation – through the aftermath of 9/11. Now America’s Mayor is a brand of coffee he fronts for $30 (£24) a bag.

Ken Frydman, press secretary for Mr Giuliani’s successful mayoral campaign in 1993, was appalled at the decline of a man he admired into a “QVC-style” coffee seller.

His former boss has not reached rock bottom yet, he believes. “The bottom would come for Rudy if he’s convicted, sentenced and imprisoned,” he told The Telegraph. “From America’s Mayor to America’s Convict.”

Mr Giuliani, already facing criminal charges in an election interference case in Georgia, pleaded not guilty in a similar case in Arizona this week.

Prosecutors apparently struggled to find him to serve a court summons while he taunted them on social media. They eventually caught up with him as he left 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 said in May that he was “disturbed” that Mr Giuliani, having spectacularly overshot his $43,000-a-month budget, had done so little to sort out his finances. His lawyer suggested that no accountant would go near him.

His name has also been mentioned repeatedly at Donald Trump’s “hush money” trial in New York, allegedly as part of a pressure campaign on Mr Trump’s former “fixer”, Michael Cohen.

New Yorkers queueing outside the Manhattan Criminal Court for a front-row seat for Mr Trump’s blockbuster trial were dismayed at what had become of the former hero of 9/11.

One member of the public predicted he would “die broke and in jail”. Another said he could simply have stayed above the political fray, adding: “All he had to do was do nothing.”

Surrendering Manhattan apartment

Mr Giuliani is now surrendering 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 sacked from his job as a New York radio host after claiming that the 2020 election had been rigged by Joe Biden. He now intends to move to Palm Beach to continue his podcasting career.

It marks his final break with the city where he became famous. He dealt a stunning blow to organised crime as US attorney for the southern district in the 1980s by securing convictions for senior mafia figures, and cut crime massively while at city hall in the 1990s.

Another of his coffee brands, “Fighting for Justice”, references 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 “compelled to tell them he was the guy who turned the city around”.

He added: “He destroyed his own legacy with self-inflicted wounds. That’s a self-made tragedy.”