Opinion: Waking up to the true Rudy Giuliani

A few years ago, I was researching a novel loosely based on the exploits of a former prosecutor who had become a brothel manager and a contractor of paid killers. I asked an investigator who was working on his case how someone could have changed so much, going from Point A to Point Z on the moral spectrum. He looked at me like I was an idiot.

“He didn’t change,” the investigator sneered. “He was always a scumbag. He went from point A to point A on the map. It just took a while for everyone else to catch on.”

Sometimes, I wonder if this is also true of Rudolph Giuliani, just last week indicted with Donald Trump and 17 other associates for racketeering and fraud charges in Georgia. Not long ago, I ventured that there was a tragic dimension to the story of “America’s Mayor.” Unlike his erstwhile “friend” and former client Trump, Giuliani, aka “Rudy,” aka “The Rude Man” has at least gestured toward decency at some points in his career. Young people may find it hard to believe, but there was a time when Giuliani was praised by even the likes of Al Sharpton for the empathetic way he spoke in the aftermath of 9/11.

A lot of people jumped down my throat, including some who worked for Giuliani directly. They pointed out that he’d crippled the city’s response to the Twin Towers by putting an emergency command center at Seven World Trade Center – near the site of a previous bombing. They held him accountable for the tragic health consequences suffered by thousands who had been denied fair warning and protective gear against the befouled air. And they talked about his long ugly history of personal vindictiveness as mayor and before that as a federal prosecutor.

Maybe they’re right. Maybe Giuliani always was a heel. Maybe it’s only a desire to turn everything into a story that makes me believe there could have been a better ending for him.

You could argue that crime was always in his DNA. A decade before he was born, his father Harold spent a year and a half in Sing Sing for robbing a milkman at gunpoint. There were allegations, unproven, that Harold was a mob enforcer. His son Rudy, born in 1944, considered a vocation as a priest before getting involved in law and politics, volunteering for Robert F. Kennedy’s presidential campaign and voting for McGovern in 1972.

It's an irony seldom remarked upon that Rudolph Giuliani first made his name in law enforcement in the infamous Prince of the City police corruption case of the early 70s, later immortalized in a Sidney Lumet film. Giuliani was one of the prosecutors involved in cultivating Detective Bob Leuci as an undercover informant against his fellow “meat-eaters” who were stealing drugs and money in the Special Investigations Unit. I knew Leuci slightly and recall that he spoke respectfully of Giuliani, who, of course, later benefited politically by being more vociferously pro-cop than many cops.

If the Rude Man’s life was a mini-series, then the 80s would have been the glory years. After gaining a reputation as a corruption fighter – so unnerving Brooklyn Rep. Bertram Podell that the pol snapped his own reading glasses during a blistering cross-examination – Giuliani became U.S. Attorney for the Southern District in Manhattan. From a certain angle, Giuliani appeared to be the antithesis of Donald Trump in that era. Trump was cashing in on his father’s name and connections, bragging about himself and his model conquests in gossip columns, and making rash business decisions that repeatedly crashed him into bankruptcy. Giuliani, by contrast, presented himself as a supremely disciplined family man working with an almost religious fervor to go after the fat cats of Wall Street and organized crime in a period of growing social inequality.

I interviewed Giuliani in 1987 and must confess that I liked him. He was loose (in a good way), funny, and gave the impression of being reasonably candid - if perhaps unreasonably obsessed with the movie, “The Godfather.” I remember that at one point in our sessions an aide came in to tell him that the office had just gained a conviction against Lynn Nofziger, the former director of political affairs for Ronald Reagan’s White House, for ethics violations. Giuliani asked me to turn off the tape recorder and then he smiled and said “great.” I was impressed because Giuliani owed much of his rise to the Reagan Administration, and I naively thought this was a man who operated without fear or favor.

Obviously, that perspective has changed since then. Nofziger got his conviction overturned. Most of the white-collar cases fell apart and so did a couple of marriages. And although Giuliani’s years as mayor saw significant drops in the city’s crime rate – largely thanks to innovations by Deputy Police Commissioner Jack Maple under Bill Bratton – that prosecutorial fervor often turned against ordinary New Yorkers. In an especially repugnant and racially-tinged case Giuliani released the juvenile delinquency record of security guard Patrick Dorismond after Dorismond was killed by undercover cops trying to pressure him into a drug deal. Giuliani claimed he was just trying to show that Dorismond was “no altar boy.” In fact, Dorismond had been an altar boy. His family received a $2.25 million settlement from the city.

It was part of a disturbing and very public turn toward authoritarianism. In September 1992, Giuliani, then running a second time for mayor against David Dinkins, incited a crowd of thousands of angry police officers outside City Hall by shouting “bullshit” about Dinkins’s plans to strengthen the Civilian Complaint Review Board. A kind of proto-January 6 riot resulted. Drunken officers jumped on vehicles, blocked Brooklyn Bridge traffic, attacked reporters and shouted racist slogans.

Giuliani downplayed the racism and, implausibly, sought to lay the blame for the violence on Dinkins. During his two terms as mayor, he made increasing forays into Culture War territory and was involved in at least 34 First Amendment cases in which the New York Civil Liberties Union defended rights of free speech against an administration intent on shutting down critics. There was a ridiculous case against New York Magazine for a bus ad that said it was “possibly the only good thing in New York Rudy hasn’t taken credit for,” and a more serious attempt to cut off funding to the Brooklyn Museum because Giuliani objected to the content of an exhibition called “Sensation.” At a mayoral forum, he declared, “Freedom is about the willingness of every single human being to cede to lawful authority a great deal of discretion about what you do and how you do it.” Jimmy Breslin called him “a small man in search of a balcony.”

Even Giuliani’s greatest moment of public acclaim looks different now. At his famous post-9/11 press conference, the stubby bellicose figure of his appointed Police Commissioner Bernard Kerik is visible behind him. That would be the same Bernard Kerik who used an apartment designated for First Responders near Ground Zero to conduct extramarital affairs while others were searching for remains and then later went to prison on federal tax fraud charges – before being pardoned by President Donald Trump. It’s fair to say that we were a long way from priestly aspirations and fighting police corruption.

We needn’t detain ourselves for too long on the years between City Hall and the beginning of the Trump era. There was much cashing in on Giuliani’s post 9/11 reputation and plentiful evidence of what his own mayoral campaign once called the “weirdness factor” in a “vulnerability study.” But Giuliani seemed to be fading from public relevancy, as demonstrated by his piss-poor showing in the 2008 Republican Presidential primaries.

It was dismaying to see him come literally roaring back with an unhinged-sounding speech on Trump’s behalf at the 2016 Republican Convention.  

There was worse to come – a lot worse. An election-time adventure in Ukraine where Giuliani was part of a Trump effort to strong-arm Volodymyr Zelenskyy into conducting anti-Biden investigations in exchange for Javelin missiles. That led to an FBI search of the former U.S. Attorney’s home and electronic devices. Then there was Giuliani’s all-in effort to support Team Trump’s campaign to overturn 2020 election results in Georgia, Arizona and Michigan. He made false claims about rigged voting machines to the Georgia State Senate and defamed a pair of Black election workers – a mother and daughter no less! – as acting like drug dealers in faking vote results (which he now admits they did not do). There was the bizarre hair dye news conference where the former mayor appeared to be melting while demanding reporters take his false claims seriously. A humiliating appearance with his pants undone in a Borat movie. And worst of all, a ghastly warm-up speech for Trump on January 6 where the most famous prosecutor since Thomas Dewey called for “trial by combat” to keep Trump in the White House.

It has generally been acknowledged that Giuliani is one of the unnamed co-conspirators in the federal indictments against Trump for being part of those efforts to overturn the 2020 election.  Trump has rewarded his former lawyer’s devotion by refusing to pay Giuliani’s legal bills at a time when Giuliani has said he is having trouble meeting some of his expenses.           

The only question left is how does this show end? Every time I think we have landed on the apotheosis of disgrace, the ultimate ironic reversal of fortune, Giuliani goes a step further. There was the ridiculous post-election press conference at Four Seasons Total Landscaping in Pennsylvania, which was meant to take place at the Four Seasons Hotel in Philadelphia and instead wound up near an adult bookshop and a crematorium. There was the hair dye meltdown and the FBI raid on his home. His license to practice law was suspended in New York and he faces potential disbarment in Washington D.C. And now the indictments in Georgia, which accuse a man who was once the most famous mob-buster in America of helping to orchestrate “a criminal enterprise.”

That would seem to be the final bitter comeuppance. Unless there’s one last twist and Giuliani decides to flip and turn against Trump, becoming a cooperator in one of these cases. I must admit that’s an unlikely conclusion. As Giuliani well knows, when a defendant begins to cooperate as part of a plea agreement there is an expectation that he or she will give a full accounting of all and any previous acts of wrongdoing to insure their credibility. The American Bar Association calls the allocution statement “an opportunity for defendants to accept responsibility, humanize themselves, and to mitigate their sentences to ensure that their punishment is appropriate for both the crime and the person who committed it.”

Now that would be a great ending to a true crime story. No one would see it coming.