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I Once Backed Rudy Giuliani. And I Know What’s Happened to Him.

He always danced on the razor’s edge between authority and freedom—until he stopped dancing and embraced the dark side.

Spencer Platt/Getty Images
Giuliani looked worse for wear at a rally for NYC mayoral candidate Curtis Sliwa in 2021.

If the wheels of justice turn slowly but grind exceedingly fine, they’re grinding at last toward Rudy Giuliani. In the hearings of the House of Representatives’ Select Committee to Investigate the January 6th Attack on the United States Capitol, Giuliani has taken center stage. On June 9, Vice Chair Liz Cheney mentioned him three times as a leader in planning Donald Trump’s attempt to overturn the 2020 election and conduct a coup d’état against the government. In the June 13 hearing, Cheney cited Republican witnesses who’d watched an “apparently inebriated” Giuliani urge Trump to declare victory on election night, long before the election had been called. Even if the House committee reports no indictable offenses, other investigations and lawsuits involving him may well indict, convict, and/or bankrupt him.

Still more fateful and instructive for the rest of us than Giuliani’s own prospects is his emblematic and substantive public role—second perhaps only to Trump’s—in fomenting today’s crisis of faith in liberal democracy in the years since Oprah Winfrey dubbed him “America’s Mayor” and Queen Elizabeth knighted him for his performance on and after 9/11. Let me offer a couple of modest suggestions about why Giuliani’s and Trump’s assaults on democracy have become so much more aggressive and unapologetic than they were 20 years ago, with worse likely to come, either from them personally or from younger offenders who have learned from them. The “why” involves certain destructive elements of personal character in Giuliani that some of us who knew him and wrote about him in the 1980s and ’90s noticed but underestimated in his performances as U.S. attorney for the Southern District of New York and as New York City’s mayor. These characterological elements that drive his excesses now were at work in those days too, and they’d converged even then with those of Trump and others before metastasizing today.

Rudy and Donald have been frenemies since well before 1987, when Trump told a reporter that “if Rudy decides to run for public office … I would be very helpful.” Two years later, Trump co-chaired fundraising for Giuliani’s first, and losing, mayoral campaign. They’re still joined at the hip, this time in public investigations and in lawsuits against them. But their assault on liberal democracy began decades ago, for personal and political reasons that they finessed back then but can no longer deny. Much has been aired about the racist, residually fascistic inclinations of Trump’s father, Fred, who made his son wealthy even as a child and sent him to a military academy before enfolding him early into his fledgling real estate development empire. But less has been said about Giuliani’s equally perverse nurture by the Brooklyn Mafia family into which he was born in 1944. His father, Harold Giuliani, an enforcer for family members’ loan-sharking, was convicted of armed robbery and imprisoned a decade before Rudy’s birth. But it wasn’t until 2000, when the late investigative reporter Wayne Barrett discovered that family secret, that anyone outside the family knew of it. Having watched Rudy as a ferocious prosecutor and mayor in the years before the secret was made public, I believe that he made his career in law and public governance partly to constrain the dark impulses in his family past but also partly because the law enabled him to reenact that vengeful force upon others under the sober cover of justice.

Giuliani and Trump at the groundbreaking for the Trump International Hotel and Tower in New York on June 21, 1995
Rose Hartman/Getty Images

You don’t have to be a psychoanalyst to suspect that Giuliani was so aggressive in publicizing his prosecutions of mobsters in the Fulton Fish Market, Pizza Connection, and “Commission” cases because he was desperate to cleanse himself of the family secret—an “out, damned spot!” reflex. At the same time, he was just as ferocious in charging his “betters” among white-collar Wall Street traders and Democratic politicians because their kind looked down on his kind.

Thirty-plus years later, Giuliani is no longer the pursuer but the pursued. After weeks spent resisting a subpoena from the January 6 committee, he surprised other Republicans by testifying on May 20 for more than seven hours, cagily, about the riot that followed his call for “trial by combat” in his speech at the Ellipse and about his leading role, hours earlier, in a meeting at the Willard Hotel to strategize about how to block certification of Joe Biden’s victory. He may have agreed to testify in hopes of softening blows that are coming from lawsuits by Capitol Police in Washington and by state election workers in Pennsylvania, Georgia, and Colorado whom his wild charges have endangered.

In Pennsylvania, for example, he’s being sued by James Savage, a voting machines supervisor accused by Republican poll watchers (armed with a doctored video) of rigging machines and destroying ballots. Giuliani touted those fabricated charges at a Pennsylvania Senate Republican majority “hearing” organized just after the election by hard-right state Senator Doug Mastriano, now the Republican nominee for governor. The Pennsylvania lawsuit’s multicount documentation of his lies nationwide makes for highly instructive reading. For instance, the suit cites the New York Supreme Court’s charges that Giuliani “repeatedly advanced false statements that there were 600,000 to 700,000 fabricated mail-in ballots … during a November 25, 2020 meeting of the Republican State Senate Majority Policy Committee in Gettysburg, Pennsylvania [and that] Giuliani also repeatedly made false statements about dead people voting in Philadelphia.”

In Georgia, partial settlement of a suit by two election workers has forced the right-wing One America News Network to admit that there was no fraud of consequence in the state’s election. But the suit against Giuliani, in which the election workers allege that he destroyed their reputations and prompted Trump backers to harass them, continues. The Colorado suit, brought by the security director at Dominion Voting Systems, exposes claims by Trump fantasist Sidney Powell, elaborated by Giuliani at an infamous press conference as hair coloring ran down his cheek, that the company’s machines had been rigged. In his deposition, Giuliani tries to blame his defamatory misstatements on the Trump campaign confusion.

Federal prosecutors in the Southern District of New York—the office Giuliani led in the 1980s—have seized his electronic devices in an investigation of his dealings as Trump’s lawyer and possibly as an unregistered foreign agent, with official and private interests in Ukraine as part of his strategy to probe Hunter Biden’s ventures there. When NPR’s Steve Inskeep asked Giuliani, “Are you the one who brought this to the president’s attention?”—prompting Trump’s impeachable phone call to Ukraine’s president—Giuliani answered, “Absolutely. Sure.”

Although Trump is the head horseman of this lawless apocalypse, and Sean Hannity and Tucker Carlson are its heralds, Giuliani has been its irresistible avatar—a particular irony for a man once seen as a champion of the rule of law. Wayne Barrett, in his book Rudy! and in a C-Span talk in 2000, recalled collaborating closely with Giuliani during a long sojourn in New Haven, Connecticut, where Giuliani was prosecuting Democrats from Queens and the Bronx whose corruption had disgraced Mayor Edward Koch. “I bonded with Rudy because we were chasing the same bad guys,” Barrett recalled, noting that Giuliani became “the hero” of his and Jack Newfield’s book City for Sale.

Barrett also recalled that he’d “felt conflicted” when Giuliani challenged Manhattan Borough President David Dinkins in the 1989 mayoral election—with Trump’s fundraising support, remember, but on a Republican Party–Liberal Party “fusion” ticket and a pro-choice, pro-immigration, pro–gay rights platform that also called for less punitive addiction treatment and housing for the homeless.

Dinkins, a deeply decent, old-school Harlem Democrat, won narrowly, partly because he’d just dethroned Koch in the Democratic primary amid scandals and racial demagoguery. But Dinkins couldn’t have hounded his corrupt fellow-Democratic power brokers out of office as Giuliani did. Four years later, Giuliani defeated him in the 1993 election, winning just about as narrowly as he had lost four years before, after some swing voters turned on Dinkins’s vision of a “gorgeous mosaic” after the Crown Heights riots and other debacles.

New York City did seem positively Hobbesian when Dinkins entered City Hall in 1990 and when he left it four years later. Violent crime was peaking. The homelessness crisis was so severe that The New York Times ran a series in the late 1980s calling the city “The New Calcutta.” The city’s unemployment rate spiked from 6.7 percent in 1989 to 11.1 percent in 1992. On Dinkins’s last day in City Hall at the end of 1993, the Dow Jones Industrial Average stood at 3,754.09. (By contrast, on Giuliani’s last day, December 31, 2001, a booming Dow would open at 10,136.99, as stock-transfer tax revenues had been flowing into the city treasury.)

Little of this was Dinkins’s fault. He’d hired 7,000 additional police officers, and crime had dropped during his last two years in office. But innocents were still being slaughtered in the crossfire of warring gangs and drug dealers, and racially charged murders were wrenching political discourse this way and that. In the subway, a clanking metaphor of New Yorkers’ common yet separate journeys, whole cars and station passageways seemed to pass rhythmically in and out of civil authority, like provinces in a country gripped by a guerrilla war. Most New Yorkers welcomed Giuliani’s pledge to end “the street tax paid to drunks and panhandlers. It’s the squeegee men shaking down the motorist waiting at a light. It’s the trash storms, the swirling mass of garbage left by peddlers and panhandlers, and open-air drug bazaars on unclean streets.”

When Giuliani defeated Dinkins in 1993, I supported him in my Daily News columns and elsewhere. A lot of what he was saying about neoliberal-Democratic fecklessness before crime and pandering to a cookie-cutter diversity had to be said. Four years later, Giuliani won a landslide reelection victory, even in “liberal” Manhattan, against liberal-Democratic icon and Manhattan Borough President Ruth Messinger, who had campaigned heavily on “diversity” nostrums but who also—and quite ironically, as Michael Tomasky noted in a New York magazine column at the time—was acquiescing in Trump’s (and Giuliani’s) promotion of the huge “Trump City” luxury apartment complex on Manhattan’s West Side. Giuliani pushed back against what he saw as Messinger’s pandering to ethno-racial “diversity” claims, having told me during his successful 1993 campaign that “if I could make up the two points I lost by in 1989 with only Black votes, it’d be healthier for me and the city.” By the time of his 1993 victory, he had done just that, with liberal grace notes on his platform. Even the democratic socialist activist and savant James Chapin told me that he considered Giuliani a “progressive conservative” on the model of Teddy Roosevelt; not so liberal on race-specific remedies like affirmative action, but strictly race-neutral in creditable ways.

During Giuliani’s first year in City Hall, I watched him tell the mostly Black Urban League’s board of directors, “I don’t have a special message for any group. People in this city … need more of certain general things—safety, education, jobs.” A nuanced discussion ensued, but “I have to move quickly,” he had told me, “because every day you wait, the problems grow exponentially.” Although I quoted that comment receptively here in The New Republic, I mentioned “the problems he is bringing on himself” and elaborated in Daily News columns on those self-generated problems, including his own “special messages” to Hispanic and Orthodox Jewish groups that backed him.

Although Giuliani contemplated the human tragicomedy with a Machiavellian prince’s supple wit in a couple of our conversations, he tensed up so tightly when emerging from his office, especially for press conferences, that even his efforts to lighten up seemed labored. Like someone else he knew, he tended to view the press as an enemy of the people, not least because we challenged his authoritarian inclinations. Still, I took his point, in his talk at a crime forum in March 1994, when he said that “freedom is about the willingness of every single human being to cede to lawful authority a great deal of discretion about what you do.” When he said it, tongues stopped cold. “I was floored. Maybe this is the real Rudy Giuliani,” said an ACLU staffer. Yet in Washington the day before, Giuliani had said rightly that “civil rights and the ability to make our own choices flow from order that prevents anarchy.” Manhattan liberals seemed not to have learned that federal authority had integrated Little Rock only because most whites ceded a great deal of discretion to lawful authority, however reluctantly. Giuliani wasn’t wrong to remind them of that reality.

Mayor Giuliani and filmmaker Michael Moore during a taping of Moore’s NBC television series “TV Nation” in May 1994
Catherine McGann/Getty Images

He wasn’t oblivious to economic violence. I recall not only his prosecuting white guys in suits and Teamsters in work clothes who backed his own president, Ronald Reagan, but also his supporting East Brooklyn Congregations, a mostly Black, self-described “power organization” that defied bankers and bureaucrats to build affordable homes.

But I also watched him send his staffers out to fight his fights like a fast and brutal hockey team—often even against agencies that weren’t even mayoral (that is, under his control), such as the Board of Education and the Metropolitan Transportation Authority, dividing everyone into friend or foe, with snarling vilifications of the foes. Those were operatic emotions, ill-suited to a city’s chief magistrate. When his old friend and deputy mayor Peter Powers told me that 16-year-old Rudy had started an opera club at Bishop Loughlin Memorial High School in Brooklyn, I realized that he sometimes lives in a libretto that glorifies vengeance and violence. If his firm, calm defiance of terror on 9/11 seemed sublime, that was because he’d been rehearsing for it all his life, drawn to chaos and brutality not because he expected to end them but because he was perversely at home in them.

Giuliani mattered to some of us when he warned us that law itself depends not only on enforcement but also on public willingness to accept its restraints on freedom. But now, the House January 6 committee, the Southern District of New York investigation, the bar association suspensions, the lawsuits, and a lot of good journalism are showing that liberal democracy’s balancing of responsible liberty and decent authority can tip all too easily into desperation and demagoguery if citizen-leaders such as Giuliani and Trump can beguile millions of their fellow citizens into craving authority more than freedom by convincing them that the former is their only route to the latter. When the creative tension between enforcement and trust succumbs to authoritarian promises of tension-free “order,” democracy’s last barrier against dictatorship falls. Giuliani has danced back and forth across that barrier for many years, for the characterological and political reasons I’ve mentioned. He’s accelerating the dissolution of public trust by chasing personal demons and seeking company with villains. It takes one to know one.