Giuliani claimed he was broke with $7,100 to his name following his bitter 2002 divorce from second wife Donna Hanover.
In fact, his scandalous extramarital affair with Judith Nathan tarnished his career as a prosecutor who tackled the mob and as New York City Mayor.
He was one of the most hated politicians in New York City until Sept. 11, 2001. The terror attacks and his photo ops at Ground Zero resurrected his career. He became known as “America’s Mayor.”
Ironically, he was caught flatfooted by the attack.
Before the jetliners struck the World Trade Center towers, Giuliani reportedly never met with the U.S. Attorney to discuss the possibility of a terror strike.
After the attack, Giuliani didn’t know who Osama bin Laden was, even though the World Trade Center towers were the target of a failed terror attack by Islamic terrorists in 1993.
Yet, he wasted no time cashing in.
Giuliani did what all washed-up pols do, he hit the speaking circuit giving high-priced speeches to corporate audiences and foreign governments. In 2006, alone, he raked in $16 million, according to The New York Times.
He earned about $5 million from his law firm and consulting firm. He made more than $10 million from just 108 speeches to various audiences around the world.
His benefactors were the same Wall Street banks, corporations and special interest groups that paid both Bill and Hillary Clinton and likely a score of other former politicians who traded on their influence in the halls of government.
In 2006, the only year records are available, Giuliani made nearly $1 million from speeches before JPMorgan Chase, Merrill Lynch and Lehman Brothers, which helped trigger the 2008 financial crisis. He’s never released the texts of his speeches.
These days, Giuliani, the son of poor, first-generation Italian working-class parents, is firmly ensconced in the one percent of Americans who stand to benefit the most from Donald Trump’s administration.
His net worth is in the tens of millions of dollars and he has posh homes Palm Beach, Fla., New York City and the Hamptons, the city’s wealthy summer retreat on Long Island.
Among other things, The Times details a long list of clients who pose a potential conflict of interest should Giuliani accept a post in the emerging Trump administration. He’s rumored to be under consideration for Secretary of State.
During the campaign Trump charged that special interests “totally owned” rival Hillary Clinton because she disclosed that she had made more than $20 million in speaking fees over the years from the very same groups. It became part of his “crooked Hillary” mantra.
In a remarkable display of hypocrisy, Giuliani criticized Clinton because the Clinton Foundation had accepted donations from the government of Qatar, despite its poor record on human rights and the treatment of women.
But he failed to mention that Qatar had also given his firm Giuliani Partners a lucrative “consulting” contract.
While the complete record of Giuliani’s speaking fees and other income since leaving office are unknown, the former mayor did his best to make hay while he had the opportunity.
From 2001 to 2008, when he considered running for president, Giuliani was out of the office for 200 days a year, Anthony V. Carbonetti, a former New York City mayoral aid told The Times.
In fact, on several occasions, Giuliani spoke at the same event as Bill Clinton. On one list of speakers, Giuliani was ranked just below Clinton, according to The Times.
Giuliani was able to ride the gravy train of corporate speaking fees because he was widely viewed as a potential 2008 presidential candidate. When he withdrew from contention, his speaking fees dried up, according Salon.
Giuliani is also a johnny-come-lately to the Republican party. Until 1975, he was a Democrat. He switched to independent and switched again to Republican to capitalize on the election of Ronald Reagan in 1980, according to his bio.
The move paid off. In 1983, Giuliani was appointed U.S. Attorney for the prestigious Southern District of New York, where he made a name for himself as a tough prosecutor.
When he first ran for Mayor in 1989, he changed stripes again. His platform included traditionally liberal issues such as “affirmative action, gay rights, gun control, school prayer and tuition tax credits,” according to reports at the time.
He lost that election to Democrat Dave Dinkins, but finally won four years later, defeating Dinkins’ bid for a second term. Giuliani won his own second term in 1997 and became the only Republican to win re-election.
In 2000, Giuliani ran for U.S. Senate. His opponent was… Hillary Clinton. The two candidates jockeyed for the lead in polls until the wheels came off Giuliani’s campaign.
In a four-week period before the election, Giuliani learned he had prostate cancer. Then, his scandalous extramarital affair with Nathan was exposed in the media. He withdrew from the campaign in May 2000, and carried a grudge against Clinton into the 2016 presidential election.
Even jaded New Yorkers were shocked by the level of vindictiveness Giuliani displayed. He even announced the split to the media before telling his wife, in an attempt to blunt news about his extramarital affair. Nathan is now his third wife.
The divorce was so bitter his children didn’t speak to him for years, and it’s unclear if they do now, according to Roger Friedman, who wrote about Giuliani for The New York Post during his mayoral terms.
In 2008, The New York Times reported on Giuliani’s dark reputation for vindictiveness. He ruthlessly attacked critics, challengers, detractors and even whistle-blowers, in many cases ruining their lives and reputations, according to the report.
Giuliani’s vindictive streak surfaced again after President Obama’s election in 2008. He became a hatchet man for the Republican party, making sharply negative attacks against the President.
At a 2015 GOP fundraiser, Giuliani uttered one of his more infamous character assassinations.
“I do not believe, and I know this is a horrible thing to say, but I do not believe that the president loves America,” he said at the gathering.
“He doesn’t love you. And he doesn’t love me. He wasn’t brought up the way you were brought up and I was brought up, through love of this country.”
Guiliani returned to that role in the 2016 campaign.
The former prosecutor who put away members of the mafia for less, defended Trump against allegations of racism, sexual assault and not paying federal income taxes for as long as two decades.