[M]ore 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.
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.
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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.
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.
I’m not a New Yorker so maybe I just wasn’t exposed to Giuliani’s alleged charms at the time. But I always just thought he was an asshole. Always.
