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.