He used to be an Italian American icon.  As a federal prosecutor he brought organized crime to its knees.  Then, as mayor of New York he made the city safe and a financial boomtown.  The horrific attack on September 11th and his praiseworthy response earned him a Time Magazine cover and British knighthood.  He was once “America’s Mayor”; now he’s a man under siege.

I met Giuliani once when he ran for mayor.  It was an introduction arranged by a member of our Institute.  My fellow officer at the time, Rosario Iaconis, and I both shared the same disturbing feeling when we left the meeting.  Giuliani was not the glad-handing politician or jovial paesano we expected, but more like a suspicious prosecutor wondering who we were, running an organization with so many Italian American contractors as members.  We never honored Giuliani nor did he ever attend one of our Waldorf-Astoria galas.  In short, the meeting went nowhere.

In fact, we weren’t keen on Rudy as an Italian American when he began the transvestite phase of his life, doing drag in public.  It got worse when he hit the late show circuit imitating bosses of the Five Families. Then in 2000, he ended his marriage to Donna Hanover without telling her – Hanover read about it in a newspaper. Despite his peccadillos and drag, Giuliani’s star was in the ascent.  He was raking in the dough – enough that Hanover got a $6.8 million settlement.  He started a consulting firm and deepened his ties with megastar Donald Trump. 

The tag team of Trump-Giuliani clearly had advantages to both men.  Giuliani now had a powerful patron and Trump gained a fiercely loyal confidant and a super sleuth.  The prosecutor who shook up Wall Street with the Boesky-Milken insider trading conviction; who made RICO arrests in the thousands – 4,000 of them including five mob bosses; who sensationalized the ‘perp walk’, was packed off to Ukraine by Trump to get the goods on the Biden Crime Family.

The Ukraine trip provoked Trump’s first impeachment. Of course, that Nancy Pelosi-inspired circus led nowhere.  However, Giuliani was still a target 16 months later.  He had made himself more vulnerable when in 2020 he took possession of the infamous Hunter Biden laptop that was abandoned at a Delaware computer repair shop and released it to the conservative media.  In 2021, the FBI raided Giuliani’s office and apartment to seize his phones.  When Giuliani offered the agents copies of Hunter’s hard drive, they demurred. (The FBI has had the original hard drive since 2019 and suppressed it.)  This month, the feds returned Giuliani’s phones.  Apparently, they found nothing; the case has been put ‘on ice’, according to the NYTimes.

So far, so good for Rudy.  He had the goods on Joe “the Big Guy” Biden, the reputed boss of the Biden Crime Family, with the Hunter laptop and a trove of documents and photos showing Joe Biden perpetrating a huge global influence-peddling operation.  The problem was that the biased corporate and social media wanted no part of it.  If Giuliani believed his work would guarantee a Trump victory in 2020, he was rudely awakened when the votes were counted.  That’s when Rudy went off the rails.

Both Giuliani and Trump became obsessed with the 2020 election being stolen at the ballot box.  Giuliani went on national television with “proof” that votes were manufactured or cast illegally.  Worse, he accused two voting machine manufacturers of programming algorithms that converted Trump votes into Biden ones.  Currently he is being investigated for election meddling in Georgia; and being sued by the voting machine maker Dominion for slander to the tune of $1.3 billion.  His NYS law license has been suspended pending resolution of the cases.

And don’t mention the January 6th Committee.  He testified for nine hours, no doubt explaining his use of the term “trial by combat” as he harangued the Trump crowd just before the Capitol breach.

How will Rudy come out of these travails?  Only Donald Trump has more legal problems than him.  No matter the outcome, the attorney fees alone are enormous.  When Trump’s National Security Advisor, Michael Flynn, was tricked into lying during a “casual” FBI visit, it cost Flynn millions of dollars in legal bills.  He was forced to sell his house, lost his job, and saw his reputation sullied.  Only a pardon by Trump kept him out of jail.

Will Rudy fare any better?  -JLM