David Lewis Schaefer
Rudy Giuliani was once hailed as “America’s Mayor” for his rescuing New York City from the depths of crime, civil disorder, and general ungovernability during his eight years in office. He restored the city’s security, cleanliness, and livability, and then leading its initial recovery during the final months of his second term from the horrors of the September 11 terrorist attack on the Twin Towers.
His reputation has since reduced somewhat: he has been ordered to pay $148 million to two Georgia election workers he was found to have defamed by falsely accusing them of having purposely mishandled ballots during the 2020 election. (The accusation was part of Donald Trump’s widely discredited, but never-ending, claim that the election was “stolen” from him.) While Giuliani had turned his reputation into a lucrative political consulting business generating a net worth of over $50 million, the judgment has compelled him to declare bankruptcy, with his already-reduced finances unlikely to cover even a reduced penalty. Giuliani’s connection to Trump was the fruit of a friendship that developed over several decades between two prominent New Yorkers. Yet, aside from their shared celebrity, they would seem to have had little in common. Starting with assistance from his father, a successful real-estate mogul, Trump built his inheritance into a multi-billion-dollar fortune through canny real-estate investments, but also by declaring bankruptcy three times.
He also earned that fortune through his use of “branding,” licensing the Trump name to other corporations. The value of his brand grew with the his 1987 book The Art of the Deal, which purported to offer the author’s get-rich tips, and even more by his decade-long hosting of the television show “The Apprentice,” where his crassness, along with his unpredictable firings of potential employees, earned him a multitude of fans. By contrast, Giuliani came to prominence as a crusading Federal prosecutor, serving for fifteen years in that position before he resigned to launch his first (unsuccessful) mayoral campaign in 1989. During his tenure Giuliani achieved justified renown for successfully prosecuting mob bosses and corrupt politicians. He even served, as historian Fred Siegel observes in his 2005 biography The Prince of the City, as the model for anti-corruption lawyers in two feature films.
Yet there was a less admirable side to Giulani’s prosecutorial conduct: his publicity-seeking habit of arresting alleged white-collar criminals in their offices, “carting them off,” as Siegel puts it, “in handcuffs like common criminals” (as if they might otherwise be flight risks). One of the best-known of those he prosecuted was Michael Milken, the “junk-bond king” of the 1980s, whom he convinced should accept a plea-bargain leading to almost two years’ imprisonment, along with a large fine. A new book by a friend of Milken’s, Richard Sandler, Witness to a Prosecution, provides, in the eyes of business columnist / Wall Street Journal reviewer Charles Gasparino, “a convincing and concerning story of how the government” in this case “targeted a largely innocent man and, when presented with proof of that innocence, refused to turn away from a bad case.” Milken was pardoned by Trump in 2020.
Giuliani’s conduct, well before his association with Trump, was not without flaws. Arguably, these flaws were mirrored in his private life: he divorced three wives (one behind Trump so far), letting his second one learn of the divorce only by announcing it on television. One can only surmise, then, that once his own aspirations for higher office – he ran an abortive campaign for the Republican Presidential nomination in 2008, leading early before losing to John McCain – were thwarted, Giuliani was lured to become a Trump acolyte by the apparent lure of continuing access to power. So enamored did he become of that access that he ended up excusing or defending, starting in Trump’s 2016 campaign, just the sorts of presidential behavior one would have expected him to denounce as a prosecutor. This is not to deny Trump’s considerable accomplishments in both domestic and foreign policy, including economic prosperity, outstanding judicial appointments, the Abraham Accords, but refers specifically to his embarrassing crudity along with his post-Presidential misbehavior, beginning with his encouraging the January 6, 2021 assault on the Capitol that aimed to reverse the Electoral College vote.
As a sometime New Yorker I was once disturbed by Giuliani’s offensive tactics in his treatment of alleged white-collar criminals (often accused of “victimless” crimes like insider trading), then celebrated his mayoral achievements. And there were two other aspects of his personal life that I liked: he was a fellow New York Yankee fan, and a learned opera buff. As in a Greek tragedy, I can only lament the tragic flaw that besmirched the late stage of his public career.
