If you’re too young to have experienced the 1990’s firsthand, if you have no memory of the O.J. Simpson verdict or the night Diana died or someone named Jewel, then you’re just going to have to take my word for this, because I know it’s going to sound bizarre and kooky, kind of like the QAnon conspiracy, but I promise you it’s true.
I know, you see him on TV now, appearing as the president’s lawyer, and you think, “Hey, when did Montgomery Burns become a real person, and why is he having an entire conversation with himself like he’s hearing voices?” I get it.
Twenty years is a long time in American politics. Believe it or not, we once bounced a speaker of the House from office because he sidestepped the ethics rules on a book deal. I mean, that wouldn’t even trend on Twitter now.
But back in the mid-90’s, when he was still a respected former prosecutor with a trademark comb-over, Giuliani turned around a city that a lot of people had come to think was no longer governable. To a New York brought low by crack and corruption and neglect, the new mayor brought a ruthless kind of metrics and accountability.
Don’t let these liberals who lived there in the 90’s, as I did, tell you how dark and despairing life was under the repressive Giuliani regime. They disdained Giuliani, but secretly they loved his mayoralty. They branded him heartless and trashed him at dinner parties, then slept blissfully above quiet, well-patrolled streets where the subway rumbled reliably and the garbage didn’t sit around for weeks on end.
That’s why, despite being a Republican in a city dominated by Democrats, Rudy won reelection with almost 60 percent of the vote. Mayors all over America openly copied Giuliani’s data-driven approach.
Rudy’s popularity plummeted during his second term, as allegations of excess overshadowed his achievements. I first interviewed him at the low point, in 1999, when the police shooting of an unarmed black man named Amadou Diallo had ignited the city and shaken his mayoralty. Rudy sat stone-faced in the living room of Gracie Mansion, summoning all the contrition he could muster.
But then came the terrorist attacks of 2001 and the memorable images of him stalking through the downtown dust, barking out orders. When he left office a few months later, at 57, he was as close to a national hero as a politician can get.
That would have been enough for most people — celebrity, adoration, easy ways to get rich. For a guy with Giuliani’s ambition and grand sense of destiny, however, the post-mayoralty wasn’t so easy to navigate.
He had wanted to run for Senate against Hillary Clinton in 2000 — and did, for a while anyway, until he got prostate cancer and then decided to use a news conference to let his wife know he was leaving her for another woman. That was pretty much the end of that.
He remained a close ally of George W. Bush, but there just wasn’t a perfect fit in national Republican politics for an ethnic New Yorker who as mayor crashed on the couch of gay friends for a while. Giuliani was a useful guy to trot out at primetime during national conventions, but he wasn’t exactly Family Research Council material.
In 2007, Giuliani decided he could overcome all that by jumping into the Republican presidential field himself. For a long while, he led in every national poll.
But then Iowa spurned him, and so did New Hampshire, and he hung around the race for months, looking for the state that would validate him. He won zero delegates.
Eight years later, Giuliani saw another window of opportunity, casting himself as a shameless apologist for his longtime friend Donald Trump. He hoped his unflinching loyalty would land him in the running for attorney general or secretary of state. It didn’t.
Apparently, though, Rudy was unfazed. Because when Trump found himself in real trouble earlier this year, Giuliani offered himself up for the arena yet again, this time as the president’s counsel and mouthpiece.
This is what it’s come to: the sad last act of a once serious man. The final, cringey chapter of the eventual biography, as painful to read as it will be to write.
You’ve seen the calamitous routine, I’m sure. Rudy proclaiming that Trump directed a payment to a porn star to shut her up, and that Trump fired FBI Director James Comey because of Russia, then having to walk back both. Rudy characterizing Michael Cohen, the president’s chief confidant for many years, as a lifelong liar — a few months after describing him as an “honest, honorable lawyer.”
Rudy saying collusion isn’t a crime, and casually referring to a secret campaign meeting, before contradicting himself and claiming it never happened. Rudy confidently telling us that Melania Trump has accepted her husband’s explanation of the Stormy Daniels fiasco, only to have the first lady’s office issue a statement saying Melania has never talked to him about anything.
It’s pretty clear by now that Trump could have hired an appellate lawyer out of the Leavenworth library and he’d have had a more coherent defense than this.
I can’t tell you what’s going on with Giuliani, who turned 74 in May. The Rudy I knew over the years was as clever an intellectual jouster as you could find; once, in Iowa in 2007, he filibustered me amiably for a full 20 minutes, knowing damn well what he was doing, because he didn’t like the question I was trying to ask.
More recently, though, he’s been known to personally call a newsroom and unleash a get-off-my-lawn tirade about something he’s just read about himself. That’s not a great sign.
But I can tell you what Giuliani’s problem has always been. As I’ve written before, in politics, as in life, your greatest strength always turns out to be your greatest weakness, and Rudy’s strength was always his relentlessness.
Bill Bratton, the police chief who devised and implemented Giuliani’s community-policing agenda in New York, once told me that Rudy’s reforms took a dark turn during his second term because he didn’t know when to let up. Aggressive policing was supposed to be the first phase of the program, Bratton said, but for Giuliani, no amount of order was ever orderly enough.
And so it is in politics, where America’s mayor has never known when to stop. He hung around the primaries way too long in 2008. He debased himself in 2016, defending Trump’s “Access Hollywood” tape when even Mike Pence was cowering under a desk.
And now here he is, charging ahead on a mission for which he’s clearly not well suited, because maybe, in a second term, there’s the promise of restoration, the hope of a powerful portfolio he will probably never get.
Say what you will, but this much I swear is true: Rudy Giuliani was a towering political figure at the end of the 20th century and a powerful force in reshaping urban America.
Maybe when this is all over, if he’s lucky, someone will still remember.