Chalk up 2023 as Rudy Giuliani’s annus horribilis. On the other hand, 2024 may even be worse. The man once known as “America’s mayor” faces financial ruin and criminal prosecution with no end in sight to his woes. The hair-dye dripping down his face at a 2020 press conference ominously presaged what would eventually follow. It took less than two decades for the former federal prosecutor and contender for the 2008 Republican presidential nomination to morph into a punchline, full-time defendant and deadbeat.
Back in the day, Giuliani garnered a reputation for crime-busting – perp-walking Wall Street bankers and sending mobsters to jail. In summer 2023, a Fulton county, Georgia, grand jury indicted him on state-law racketeering charges along with the 45th president and a host of supporting characters.
As the year closed, Donald Trump’s henchman-in-chief lost a $148m defamation verdict in federal court for sliming two Georgia election workers. Days later, he filed for bankruptcy. Yet even before that he was banging a tin cup.
Reports repeatedly surfaced of Giuliani personally begging his godfather to pick up his legal tab. Long story short, that didn’t happen. Instead, Trump threw a $100,000-a-plate fundraiser to help pay his legal bills, but apparently little else.
Giuliani’s sell-by date had long expired. Then again, Trump had already done plenty for – and to – his sometime sidekick.
Depressed and drinking to excess after his failed-presidential run, Giuliani secretly recovered at Trump’s Palm Beach home years earlier. “We moved into Mar-a-Lago and Donald kept our secret,” Giuliani’s third wife, Judith Giuliani, said in Andrew Kirtzman’s 2022 book, Giuliani: The Rise and Tragic Fall of America’s Mayor.
Even knowing Giuliani’s capacity to go off the rails, Trump had considered him for a cabinet position, then effectively deputized him as his personal emissary to dig for dirt in Ukraine on Hunter Biden and subsequently tapped him as counsel in Trump’s efforts to overturn the 2020 election.
In a word, Giuliani isn’t the only one with seemingly addled judgment. As luck would have it, Rudy’s relationship with alcohol has gained the attention of federal prosecutors. His conduct and possible inebriation on election night 2020, could undermine a Trump defense based upon reliance on counsel.
“The mayor was definitely intoxicated,” Jason Miller, a senior Trump adviser and a veteran of Giuliani’s presidential campaign, told the House special committee last year. “But I do not know his level of intoxication when he spoke with the president.” For the record, Giuliani excoriated Miller and denied his contentions.
Rudy’s bankruptcy filing lists his assets as between $1m and $10m, his debts between $100m and $500m. Under the category of “Taxes and certain other debts you owe the government”, he is on the hook to the IRS for more than $720,000 and to New York state for over $260,000.
Beyond that, he is fighting over legal bills that amount to millions, and lists Ruby Freeman and Wandrea Moss, the plaintiffs in the $148m defamation case, as creditors. Other cameos include Smartmatic USA Corp; US Dominion, Inc; Robert Hunter Biden, the president’s wayward son; and Noelle Dunphy.
Freeman and Moss are not alone. Giuliani also allegedly defamed Smartmatic, Dominion and their respective voting machines in connection with the 2020 election. As for Hunter Biden, think of it as a cage match.
Dunphy’s claims, however, offer another window into Rudy’s strange universe. In May 2023, Dunphy, a former Giuliani associate, sued him for $10m, alleging “abuses of power, wide-ranging sexual assault and harassment, wage theft and other misconduct” including “alcohol-drenched rants that included sexist, racist and antisemitic remarks”.
Her pleadings add, “Many of these comments were recorded.” According to Dunphy, he chugged Viagra non-stop. “Giuliani would look to Ms Dunphy, point to his erect penis, and tell her that he could not do any work until ‘you take care of this’.”
Dunphy’s complaint also alleges that Giuliani asked Dunphy “if she knew anyone in need of a pardon” because “he was selling pardons for $2m, which he and President Trump would split”.
She also asserts that she was “given access to emails from, to, or concerning President Trump, the Trump family … and other notable figures including … President Recep Tayyip Erdogan of Turkey …” With the Middle East on fire, that thread may prove more than simply interesting.
In 2017, in the early days of the Trump administration, Giuliani represented Reza Zarrab, a Turkish-Iranian gold trader charged with helping Iran to dodge US sanctions and launder hundreds of millions.
During a “contentious” Oval Office meeting, Giuliani pressed for the release of Zarrab as part of a potential prisoner swap with Turkey. In turn, Trump reportedly urged the US Department of Justice to drop its case. Eventually, Zarrab accepted a plea deal and emerged as a cooperating witness.
Recently, Erdoğan has defended Hamas and compared Hitler favorably to Benjamin Netanyahu, Israel’s prime minister. Meanwhile, Iran is now trying to take credit for the horrors of 7 October.
Giuliani is “used to willing people to do his bidding, the same way Trump is”, Ken Frydman, a former Giuliani campaign press secretary, told CNN earlier in December. “And it’s not working any more. So he’s just flailing around … desperately trying to stay out of jail.”
There’s family history there. Rudy’s father, Harold Giuliani, was a stick-up man and leg-breaker for the mob. He also did prison time at Sing Sing, a correctional facility in upstate New York.
Lloyd Green is an attorney in New York and served in the US Department of Justice from 1990 to 1992
