Rudy in Brazil

Palácio do Planalto

Former Mayor Rudolph Giuliani during a 2019 visit to Brazil.

Nothing swirling around Rudolph Giuliani now is out of step with the person depicted 26 years ago in a 464-page vulnerability study, a report that he commissioned for his second run for mayor.

If Richard Nixon’s deep paranoia and Bill Clinton’s insatiable sexual appetite drove earlier impeachment episodes, Giuliani’s apparent fall from grace is central to the Trump-Ukraine psychodrama. A crusading prosecutor, mayor/savior of a crime-ridden Metropolis, and sudden hero on America’s darkest day might go down in history as the ringleader of a transnational scheme trading military aid for political dirt. Many a media report in recent months has cast Giuliani’s demise as some sort of Greek tragedy.

Except, that’s nonsense. Little in the current allegations against the mayor is a surprise to anyone who remembers a few of the darker, more bizarre moments when Giuliani was Emperor of the City: the public humiliation of his second wife; the unapologetic rush to smear Patrick Dorismond, slain by an undercover cop; the ouster of Police Commissioner Bill Bratton, who had become Gotham’s crime-reduction cover boy; and, yes, the personal attack he unleashed on a ferret-friendly caller to his radio show.

What the vulnerability study reveals is how many of these “issues” were apparent before Giuliani became mayor—and well before he became counsel to the 45th president of the United States.

The study was opposition research Giuliani ordered to be done on himself. It was prepared for his 1993 mayoral campaign, a rematch of the race he lost narrowly to David Dinkins in 1989. The aim was to “inoculate” him against all potential attacks from his opponent. The result is a roadmap to the traits that have placed Giuliani at the center of our nation’s political crisis.

An Internal Report

The Rudolph W. Giuliani Vulnerability Study (posted in full below) was so incisive that, according to Giuliani biographer Wayne Barrett, the candidate ordered all copies destroyed once it had been absorbed by his closest aides. This compilation might fall into the wrong hands and give enemies the intelligence needed to dismantle him. (Apparently, at least one copy survived.)

Sun Tzu is quoted on the cover page: The art of war teaches us to rely not on the likelihood of the enemy’s not coming, but on our own readiness to receive him; not on the chance of his not attacking, but rather on the fact that we have made our position unassailable.”

Produced by Republican consultant Christopher Lyon and a lawyer named Ronald Giller, the report catalogues the chinks in Giuliani’s behavior and professional record. It is a thick ledger consisting of clippings from newspapers, periodicals and interviews along with letters and memos that inventory Giuliani’s exposure in four areas: Political, Department of Justice, Private Practice and Personal.

No weakness is left unturned. Questions are raised about a “weirdness factor” in Giuliani’s 12-year (or was it 14-year?) marriage to a second cousin, about his temperament and soundness of judgment, and about the bold tactics he used in vaulting to Associate AG in Ronald Reagan’s DOJ and appointment as U.S. Attorney for the Southern District of New York.

Each section is a trove that presents the “charges” Giuliani might face in his bid for office. Anticipating the attacks, the report offers rebuttal strategies to refute a criticism, ignore it or re-spin it into a credit. For example, “You say Rudy is overzealous, I say he hates criminals.” And the “ruthless” rap pinned on him should be parried by pointing to his accomplishments: “Rudy is a no-holes-barred crime fighter who shook things up and achieved unprecedented success.”

Unrestrained Aggression

Reading the scrupulous research into Giuliani’s entire public-service career back then—the posts he held in two stints with the DOJ (1970-1976 and 1981-1989)-—it’s easy to draw parallels between problems he faced in 1993, the issues that cropped up during and beyond his terms in office, and those that persist in his service to the Trump administration.

It’s not new, for instance, for Giuliani to be accused of involvement in “dirty tricks” described as “nefarious.” Today the accusation is that he coordinated a whispering campaign against a U.S. ambassador and dangled military aid to squeeze the Ukrainian government into investigating former Vice President Joe Biden. In the 1993 report, however, a less spectacular allegation was seen as potentially threatening to Giuliani’s chances to become mayor.

During his teeth-cutting years in the DOJ, Giuliani took over Project Haven, a probe into illegal use by U.S. taxpayers of offshore tax havens. It was one of a handful of IRS investigations that became the focus of later Congressional hearings concerning law-enforcement overreach. One Haven operation involved a confidential informant arranging for “female entertainment” to distract a Bahamian bank official visiting Miami, while the informant entered the man’s hotel room, stole his briefcase and returned it after IRS agents photographed the contents. When IRS commissioner Donald Alexander had concerns about such tactics and suspended the operation, Giuliani “reportedly attempted to convene a grand jury to investigate the impeccable IRS commissioner,” wrote Vanity Fair in 1989 and “nearly ruined Alexander.”

The study also mentioned Giuliani’s firing of DOJ officials because of party affiliation, but that didn’t draw much attention because it fell within the rules of hardball. Of greater worry was the need to address the charge that he was known for making deals with major wrongdoers in order to score wins, whether it was cutting defense contractor McDonnell-Douglas executives a break by absolving them of personal responsibility for paying $1.6 million in bribes to Pakistan, or writing a letter to support legendary drug pusher Nicky Barnes’s request for lighter sentencing.

Giuliani’s apparent insatiable need for the limelight, which comes at the cost of topping each incautious statement he makes on cable news these days, was visible a generation ago. He was seen as a shameless publicity seeker, whose hunger for headlines may have led to bad prosecutorial strategy.

There was, for instance, the choice of having a daughter gather information and testify against her mother, a co-defendant in the 1988 trial of former Miss America and one-time city commissioner Bess Myerson. The move failed, the case fell apart, and Giuliani’s team was accused of using “gutter” tactics.

It wasn’t his only time down there. In prosecuting disgraced Bronx Democratic boss Stanley Friedman, Giuliani wiretapped the opposing counsel’s pre-trial preparations. While Giuliani certainly won his share of white-collar crime convictions, he also perp-walked and humiliated Wall Street figures against whom no case ever materialized. A master at using the RICO statutes, he squeezed one small securities firm so hard it busted a few months before its conviction was overturned. “Cooperate or be destroyed” was the goal, according to the study.

From Haiti to the steps of City Hall

Giuliani’s performance in high-profile cases was not the only arena that left him open to potential problems. He also accrued liabilities in the DOJ as a policy maker/implementer/enforcer, and as a private attorney and mayoral wannabe between 1989 and 1993.

As #3 man in Reagan’s DOJ in charge of Immigration and Naturalization Services, Giuliani shaped and defended the administration’s racist policy toward the country being run by dictator Baby Doc Duvalier. He uttered blatant mistruths, claiming that political repression “simply does not exist now” in Haiti and falsely asserting that the Vatican’s man in Port au Prince, the papal nuncio, had told him as much. Giuliani’s argument was that the Haitian boat people were not granted asylum because they were not refugees fleeing persecution. They were portrayed as a threat to national security who should be deported.

Inhumane treatment followed: placement of thousands in detention camps; incarceration of women and children; splitting up family members. And Giuliani, seen as the architect of a racially motivated policy, “vigorously defended [it as] necessary to prevent Miami from being overwhelmed by crime and disease,” according to one UPI article quoted in the study.

The report devotes 32 pages to recount the angry 1992 protest against Dinkins’ proposed all-civilian police complaint review board that Giuliani helped stoke into a City Hall rampage. The study headlined the serious liabilities triggered by the affair: “Rudy Giuliani’s performance at the police rally demonstrates that he is temperamentally unfit to be mayor of the City of New York. His inflammatory profanity-laced screeching before thousands of gun-toting, off-duty New York City cops turned an overtly racist police rally into a dangerous police riot.”

The authors suggest that Giuliani try to limit the damage to his mayoral bid by citing instances when he went after corrupt cops—but they acknowledge the big problem was his unwillingness to rebuke those taking vicious “pot-shots at the mayor.” Mike McAlary described him as “The Human Scream Machine” in the Post, Sept. 18, 1992). And the New York Times opined that in berating the mayor, Giuliani was “apparently betting—irresponsibly—that divisiveness will win votes.”

Private practice and lucre

Giuliani left the DOJ on Jan. 1, 1989 after serving more than five years as U.S. Attorney. He was getting ready to run for mayor.

He joined White and Case, a white-shoe law firm. The study raises two red flags about this association. First, W&C, “represented a long list of politically unsavory clients, including [Panamanian dictator and drug lord] Manuel Noriega…” Second, “Giuliani’s extraordinarily high salary for so little work raises the question: What did White & Case expect from Giuliani if elected mayor?” He received $16,250 per week, which came to $260,000 over four months, before taking a leave of absence. On a yearly basis, he was making ten times what he did as U.S. attorney. According to the report, his pay was much higher than what other partners earned.

It was far from the last time Giuliani cashed in. After leaving office in 2001, he parlayed 9/11 into large advances for books, millions in speaking fees and several enriching business ventures, like the consultancy Giuliani Partners, where he sold his self-proclaimed ability to fight terrorism and provide cyber security systems. Recent estimates of his net worth range from $45 million to $60 million.

Giuliani left a law firm where he made $4 million to $6 million in 2018 to become Donald Trump’s pro bono attorney, a point that he emphasizes. But this noble sacrifice does not take away his calling card as a power broker, as the man with direct access to the Oval Office and the levers of government.

Rudy and Donald

The only reference to Donald Trump in the report comes from a New York Post article (Nov. 21, 1987) in which Trump foresees Giuliani running for election. “If Rudy decides to run for public office, I hold Rudy in very high esteem and I would be very helpful to Rudy.”

He offered further praise: “The development community should love Rudy because he’s gone after organized crime and other things that adversely affect the development community.” In this coherent statement, it is clear that Trump appreciated how Giuliani’s major courtroom wins benefited builders and opened the door to opportune deals.

A recent New York Times article speaks of their relationship. “They had known each other for nearly 40 years. Mr. Trump was the gaudy, gold-veneered developer who somehow navigated the shoals of organized crime, labor racketeering and official corruption in the New York real estate market of the 1980s, even as Mr. Giuliani was becoming so well known as a federal prosecutor.” The article supplies the fact that Trump was co-chairman of Giuliani’s first campaign fund-raiser in 1989.

And suddenly, when impossible presidential long-shot Trump emerged, Giuliani became his most daring advocate, and arguably giving him the narrow margin of votes needed to snatch victory from Hillary’s grasp by promoting a last-minute FBI probe of her emails.

As a reward for his extreme loyalty, there was talk that world traveler Giuliani wanted to be Trump’s Secretary of State. That didn’t happen. Instead, he’s become the president’s lawyer, conspiracy theorist and political fixer.

Yet the Vulnerability Study reveals a fundamental contrast between the mayor and the president. Trump would never allow for such a self-doubting dossier. Giuliani knew he had flaws and had to anticipate criticisms. Unlike the president, he also has a history of articulating high-minded ideals—words that now seem tinged by irony.

“The cases I get the most emotional about are the political corruption cases,” he professed in 1987. “There’s something extra-aggravating when a person who holds political power violates his oath of office, because it has a tendency to unhinge public confidence in government.”

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Read the Study

Intro & “Political Vulnerabilities: Reagan Republican”

Political Vulnerabilities: “Racist”

Political Vulnerabilities: “Sexist,” “Anti-Gay,” “Ethnic Vulnerabilities,” “Flip-Flops”

“Dept. of Justice Vulnerabilities” (Operation Tailwind, Haiti and more)

Dept. of Justice Vulnerabilities: “Cases Lost”

Dept. of Justice Vulnerabilities: “War on Drugs,” “Tax Evaders,” “Overzealousness”

Dept. of Justice Vulnerabilities: “Ruthlessness,” “Publicity Seeker”

Section C: “Private Practice Vulnerabilities”

Section D: “Personal Vulnerabilities”

Section E: “Accusations and Accolades”

Section F: Appendix