Why I'm still trying to figure out what happened to Rudy Giuliani

On Oct. 8, 2019, The New York Times published my opinion essay “What Happened to Giuliani?” More than three years later, I’m still not sure of the answer.

“The man I worked for is not the man who now lies for Trump,” I wrote. I wanted to favorably introduce readers to the “old Rudy.” But I also hoped to snap him out of Donald Trump’s spell. That has turned out to be an impossible task.

I also hoped to snap him out of Trump’s spell. That has turned out to be an impossible task.

Ever the contrarian, Rudy Giuliani dismissed my column and the “liberal” newspaper it appeared in. He was busy trying to dig up dirt on Hunter Biden, anyway. But Ukrainian sidekicks Igor Fruman and Lev Parnas were arrested Oct. 9 — the day after my Times op-ed ran. 

I met Rudy Giuliani in February 1992, when I was hired as press secretary on his rerun mayoral campaign against Democrat David Dinkins, the city’s first Black mayor. Giuliani had lost to Dinkins by 2 percentage points in 1989; he defeated Dinkins by 2 points in 1993, a four-point swing. 

Back then, Rudy at least seemed like a regular guy from Brooklyn. Suits off the rack and sensible dress shoes. A quick study, a policy wonk, a terrific litigator. He smoked cigars but didn’t drink, at least not on the campaign trail. And he listened to me and others, because he wanted to win. 

Rudy’s first term was arguably the most successful in the city’s history. His tough-on-crime policing strategies and tactics reduced murders in New York City from 2,245 in 1990 to under 800 in 1997, the end of his first term. And murders fell even further in 2001, Rudy’s last year as mayor. Indeed, the murder rate has continued to fall in the 20-plus years since: The city’s low-water murder mark was 292 in 2017; city officials said 488 murders were recorded citywide in 2022. 

So how to square the mayor I worked for with the Donald Trump toady? Maybe longtime Rudy haters are right: Perhaps he was always like this, and I missed the early warning signs.

I believe in body types. I also believe that lifelong personality characteristics are set by the age of 4, if not earlier. After that, we can still modify our personalities. But we can’t change our genetics — who we are, deep down. 

Imagine young Rudy Giuliani. He was the only child of a doting mother and a mobbed-up father, studious and serious and at the top of his class. Catholic school gave him the moral high ground and a willful sense of self-certitude. He considered becoming a priest until his “budding interest in the opposite sex” emerged.

(By comparison, Trump was reportedly a lazy student who was shipped off by his affluent parents to the New York Military Academy.) 

Rudy did change, at least outwardly. The 9/11 hero became an anti-democratic collaborator.

But Rudy did change, at least outwardly. The 9/11 hero became an anti-democratic collaborator. No longer the darling of the New York tabloids, he was the butt of late-night jokes. He remains in legal jeopardy and could even be barred from practicing law in multiple states.

So returning to my original question: How did this happen? Only Rudy knows for sure. Nothing he says or does makes sense anymore, whether it was his bizarre news conference outside Four Seasons Total Landscaping, sticking a hand down his pants in “Borat,” shaving in an airport restaurant or appearing oblivious to some sort of dark dye running down his cheeks. 

I’ve tried and failed to reason with Giuliani publicly. I have appealed to his “former self” and his future legacy. At one time, I hoped Giuliani would come to his senses and abandon Trump. Instead, he dug in deeper, becoming the face of Trump’s election fraud charade.

And then, on Jan. 6, 2021, Rudy metaphorically lit a match to the Constitution and personally exhorted the insurrectionists to “have trial by combat” before they stormed the Capitol to “stop the steal.”  

That’s why I keep speaking out — I feel almost duty-bound to use my platform to keep exposing Rudy’s lies, writing columns, doing interviews and consulting on documentaries about him.

My mother asked me in late 2019 why I “keep kicking Rudy while he’s down.” After all, she noted, “he helped make your career.” 

“Because,” I responded, “he keeps getting back up.” I’m still waiting for him to throw in the towel.