Rudy in Reverse: A Retrospective of Wretchedness

The father went to Sing Sing for sticking up a milkman. The son is even worse.

MAKER OF MYTHS, exploiter of national trauma, disseminator of Russian propaganda, spreader of plague, friend of organized crime, ruthless opportunist, fallen crusader, media whore, Trump apologist, feckless performance artist, and, above all, selfish asshole. To fully appreciate the abject wretchedness of Rudolph William Louis Giuliani—in the event that he dies of covid-19, and sympathetic obituaries whitewash him—it helps to work backwards, Benjamin Button style…


After showing symptoms for five days, a period in which he traveled and spoke extensively, Rudy Giuliani tests positive for the novel coronavirus. It is December 6, 2020. “I’m…feeling good,” he tweets, from a hospital bed at Georgetown Medical Center.


In his capacity as personal attorney for Donald John Trump, Giuliani is the driving force of a quixotic crusade to overturn the election results and keep the president in the White House. It is late autumn, 2020. In service to Trump’s “rigged election” campaign, which will raise some $200,000,000 in two months for the outgoing president, Rudy repeatedly beclowns himself. He brings an “actress” to a hearing in Michigan that is immediately spoofed by SNL. He argues before a judge for the first time in decades, and his suit is thrown out with prejudice. Hair dye oozes down his cheeks as he sweats during a press conference. He appears in the second Borat feature on his back, on the bed of a hotel room, unzipping his pants, in the company of a woman young enough to be his granddaughter, with whom he is aggressively flirting. He holds a press conference at the Four Seasons in Philadelphia—the Four Seasons Total Landscaping, a lawn and snow removal operation located between a crematorium and a sex shoppe—only to have half the reporters leave when the election is called for Biden.


In an attempt to manufacture “dirt” on Joe Biden and his son Hunter, Giuliani pressures the Putin-aligned Ukrainian oligarch Dmitri Firtash, whom the U.S. wants to extradite to face corruption and bribery charges, for help. It is the summer of 2019. Firtash is made to understand that in exchange for retaining the services of Rudy’s attorney pals—Victoria Toensing and Joseph diGenova—and helping investigate the Bidens, Rudy will make his legal issues go away. This all culminates in the Trump phone call to Ukrainian president Zelensky in July for which he will be impeached. In August, Toensing and diGenova argue before Attorney General Bill Barr that Firtash’s charges should be dropped.


After 18 months of radio silence, Giuliani turns up on the talk shows to announce that he is Trump’s personal attorney, perhaps to take advantage of attorney-client privilege. It is May 2018. The Mueller investigation is in full swing. Rudy fills the information void, and begins crafting the anti-Mueller messaging, hammering home the theory that a sitting president, even a seditious one, cannot be indicted, and that the investigation is illegitimate—a witch hunt.


Giuliani Security, Rudy’s cybersecurity company, is in Kharkiv, Ukraine, to ink a “security” deal with the mayor, Gennady Kernes, formerly a bigwig in the Party of Regions, and an ally of the disgraced pro-Putin president Viktor Yanukovych—Paul Manafort’s old client. It is May 2017. James Comey has just been fired, and Russian jackals are yukking it up with Trump in the Oval Office. Giuliani will continue servicing various cities and politicians in Ukraine. His appearances in the media coincide with meetings Trump takes with Putin or Putin’s ambassadors.


Fearful of a formal Senate confirmation hearing, which would require him to answer uncomfortable questions under oath, Giuliani is named Trump’s informal cybersecurity advisor. It is January 2017. This is widely mocked; the website of Giuliani Security is not even secure.


After campaigning more or less openly to be Trump’s Secretary of State, Giuliani abruptly withdraws from consideration. It is December 2016.


With a shit-eating grin, Rudy Giuliani announces an imminent October Surprise. It is October 2016. He turns out to be right: soon after, James Comey sends his memo to Congress, advising that a new laptop has been found at the home of Anthony Weiner, and the investigation into Hillary Clinton’s emails has been reopened. Internally, this was the work of rogue agents in the FBI’s “Trumplandia” New York field office, who painted Comey into a corner. Rudy appears to have had advance knowledge of this.


At the Republican National Convention, Giuliani delivers an ugly, impassioned speech, calling out Islamic extremism. It is July 2016. “It’s time to make America safe again,” he says. “It’s time to make America one again.” And: “What I did for New York City, Donald Trump will do for America.” (Ironically, this will prove true, insofar as what Rudy did for New York was fuck up the emergency planning and crisis management so badly that many people needlessly died).


Giuliani leaves the venerable law firm at which he is a partner, Bracewell Giuliani. It is January 2016. During his tenure there, Rudy was lead counsel for Purdue Pharma, makers of OxyContin, and arguably the corporation most responsible for the nation’s opioid crisis. As soon as he cleans out his office, the firm reverts back to its original name, Bracewell LLP.


After a promising start, Rudy Giuliani withdraws from the 2008 presidential race. It is January 2008. His campaign is almost $4 million in the red. The torpedo that sinks the campaign is the indictment of his close associate and one-time driver, Bernard Kerik, the former New York Police Chief and one-time nominee for Homeland Security Secretary, on 16 counts of tax fraud and other federal charges. Kerik would later serve four years in prison.


Giuliani Partners enters into a joint venture with Sabre Technological Services to start an environmental decontamination company called Bio ONE, which is tapped by American Media, Inc. to clean its Boca Raton facility that had been the victim of an anthrax attack. It is January 2004. The plan is for Bio ONE to render the offices so clean that they themselves would occupy them going forward; Giuliani himself would be the first to enter the newly-cleaned building. Thus does Rudy’s outfit get unfettered access to the National Enquirer’s mammoth vault of photographs, including untold thousands that had never and would never run. Bio ONE is ultimately unable to successfully decontaminate the facility.


Giuliani Partners is formed, to monetize America’s Mayor’s perceived success on 9/11. It is January 2002. Among the beneficiaries of Rudy’s mercenary boosterism: Merrill Lynch, then under investigation by New York attorney general Eliot Spitzer; WorldCom, the telecommunications company wracked by scandals and on the verge of bankruptcy; Aon, the insurance giant that had lost 176 employees in the attacks; Nextel, the telecom outfit whose lousy product contributed to the communication problems in New York on 9/11; and drug merchants Purdue Pharma.


It is September 2001. Rudy Giuliani is wandering around Lower Manhattan, covered in dust from the terrorist attacks. He is wandering around because his Office of Emergency Management command center has been destroyed. The command center has been destroyed because he insisted, despite near-universal objections, to locate it in the World Trade Center complex. As Dan Collins and Wayne Barrett write in their book Grand Illusion: The Untold Story of Rudy Giuliani and 9/11:

If the center had been elsewhere, all the dramatic visuals that turned the soot-covered Giuliani into a nomad warrior would instead have been tense but tame footage from its barren press conference room, where reporters had been corralled prior to 9/11 for snowstorms and the millennium celebration….Had he been able to get into and operate from a command center he says he “headed” for shortly after 8:46 that morning, he might have been more effective, but he also would have been less inspirational.


Mayor Giuliani is Cleaning Up New York—what we residents refer to as the “Disneyfication” of Times Square. It is 1999, and Rudy has his sights on the city’s strip clubs. Billy’s Topless has famously become Billy Stopless. Many of these establishments are fronts for the mob, against which Giuliani had waged a very public battle in the mid-80s. But if the goal is to “re-zone” and move gentlemen’s clubs to other parts of the Five Boroughs…why are Gambino-affiliated businesses spared? “Why was Scores,” Nia Molinari asks on PREVAIL, “which was allegedly Gambino-run, not shut down like the other clubs, even after being nailed for racketeering?”


Mayor Giuliani appoints Semyon “Sam” Kislin to New York City’s Economic Board of Development Corporation. It is 1996. Kislin was a big donor to Rudy’s first mayoral campaign in 1993, and will donate even more to his 1997 campaign. According to a 1994 confidential FBI report, cited by Robert I. Friedman in his book Red Mafiya, Kislin is a “member of the Ivankov organization”—the Russian mob. “These sources say that Kislin’s commodities firm has been involved in laundering millions of dollars, and co-sponsored a visa” for a notorious Russian hit man.


The Mafia Commission Trials are making Rudy Giuliani’s reputation as an anti-mob crimefighter. It is November 1986, the end of the trials which began the previous February. Eleven organized crime figures, including the heads of four of the five families, were convicted for extortion, racketeering, and murder for hire. And the fifth? The head of the Gambino family, Paul Castellano, was shot dead with his underboss, Thomas Bilotti, before he could be convicted.

This is a landmark trial, and a victory for the good guys over the bad guys—but only a partial one. John Gotti and Sammy “The Bull” Gravano, who replaced Castellano and Bilotti, would evade prosecution for another four years. More importantly, the decapitation of the Five Families allows the fledgling Russian mafiya to move into New York.


As the U.S. Attorney for the Southern District of New York, Giuliani pioneers the “perp walk,” whereby key perpetrators are arrested and brought it in very public, and humiliating, ways. It is 1983. Some of the “perps” are not actually guilty of wrongdoing, so this is largely political theater.


It is March 1981. Ronald Reagan, the new President of the United States, names Rudy Giuliani Associate Attorney General. One of Giuliani’s first official acts is to send a memorandum to the Acting Assistant Attorney General, Criminal Division, asking for a letter requesting a written report on “CIA Referral—Alleged Foreign Government Interference With 1980 Presidential Election.”

What does Giuliani know about election interference? As Lincoln’s Bible points out in her chat, Rudy’s closest contact in presidential politics is probably Rabbi Greenwald, a member of CREEP and, per Friedman, a close associate of the Russian mob, whom Giuliani knew from his time in New York.


Rudy, a Democrat who had voted for George McGovern in 1972, switches his party affiliation to Independent. It is 1975. He does this to work at the Department of Justice during the Ford Administration.


After serving as president of his class in his sophomore year at Manhattan College, Giuliani does not win re-election his junior year. It is 1963.


Leo D’Avanzo owns a Brooklyn bar called Vincent’s, out of which he runs a gambling and loan shark operation. It is 1948. He has need of muscle, an enforcer to collect money when needed. He decides to hire his brother-in-law: Harold Giuliani. Harold is the father of Rudy, who is four years old. Leo is Rudy’s uncle. Leo D’Avanzo is associates with Ralph Eppolito, allegedly a “made man” in the Gambino family.

The same Gambino family that avoided decapitation in the Commission Trials.

The same Gambino family whose strip clubs were spared during the “re-zoning” of New York in the late 90s.


On East 96th Street in Manhattan, a milkman is making deliveries. A man emerges from the shadows, gun in hand, and sticks up the milkman. It is 1934. The armed robber is Harold Giuliani, who is caught, convicted, and sent to Sing Sing.

The acorn, the tree.

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For further reading, please see the PREVAIL interview with Portlus Glam, who has done extensive research on Giuliani’s shenanigans in Ukraine; my guest post at Alexandra Erin’s Substack, “The Myth of America’s Mayor;” and Nia Molinari’s “F—k Giuliani” PREVAIL piece.

Photo credit: Gage Skidmore. Former Mayor Rudy Giuliani speaking with attendees at the 2019 Student Action Summit hosted by Turning Point USA at the Palm Beach County Convention Center in West Palm Beach, Florida.