The Mystery of Rudy Giuliani’s Moral Decline Isn’t Such a Mystery at All

Rudy Giuliani at the 2016 Republican National Convention. Photo: Brooks Kraft/Corbis via Getty Images

Things that now seem inevitable often came first as surprises, and if you look back at the campaign, Rudy Giuliani’s unhinged, grasping embrace of Donald Trump was in fact slow and cautious — at least at first. This evolution (or devolution) over the course of this latest election almost functions as something of a stand-in for Rudy’s career: a long arc of slowly moving rightward over the decades, from district attorney to America’s mayor to Fox News talking head. Then, suddenly, with a snarling acceleration, emerging on the national stage someone who looks almost unrecognizable as the same politician who, on 9/11, ached alongside a diverse city and a frightened country in shock. Now, instead, he was haranguing his enemies with vicious personal attacks, race baiting, denying reality alongside the same conspiracy theorists who doubted the 9/11 attacks. He was the top choice of Steve Bannon, the alt-right’s voice in the Trump administration, to be secretary of State. But it turns out he won’t be — news broke on Friday afternoon that Giuliani had withdrawn his name from contention — leaving him to grapple with the public embarrassment of campaigning so openly, right after the election, for a job he thought was in the bag. The talk is that his old client list was going to cause him problems in the confirmation hearings. Whatever the reason, he’s not going to make any year-end winner lists now; his strange turn was all for naught. Or was it such a turn? If you’ve been looking closely, the clues have been there for years: Giuliani’s Trump era is less an abrupt departure from his true personality than the purest distillation of it.

As late as last year, though, Rudy was eyeing up Jeb Bush and the moderate, patrician Establishment he represented. (He’d always had good relations with the Bushes.) But Jeb was gone fast. The only Republican Giuliani really didn’t like, personally or ideologically, was Ted Cruz — the Texas senator is part Elmer Gantry and part Princeton, and Rudy doesn’t care much for either of those parts. So once it was clear it was either going to be Cruz or Donald Trump, which was mid-April, the time of the New York primary, he chose the latter.

And once he chose, did he choose. Giuliani semed to be on Fox almost as often as O’Reilly and Hannity. He appeared constantly at Trump rallies. He defended Trump on virtually everything, up to and including the infamous pussy-grab video, and he said some of the most vicious things about Clinton that were said during the entire campaign, charging that the Clinton Foundation was a criminal enterprise, dropping baseless hints about her health, and seizing with glee on the calls to “lock her up.” (“When I see her, I see her in an orange jumpsuit, I’m sorry, or at least a striped one,” he said.) On Election Day, he declared happily that “this is probably one of the greatest victories for the people of America since Andrew Jackson.”

And of course, there was that speech. The convention speech. Spitting, seething, raising his arms, baring his teeth, popping his eyes, arching his eyebrows, he looked at moments like he was about to burst out of his suit and turn into a werewolf. Fred Siegel, a sympathetic Rudy biographer, recalls watching the speech and turning to his wife in disbelief. “Too operatic,” Siegel told me. “Rudy loves opera, and he gave in to it.”

He had always had a major nasty side. We all know that. But this Rudy, this convention-speech Rudy, this Trump-is-a-great-man Rudy, this throw-the-Clintons-in-jail-and-by-the-way-Hillary-is-dying Rudy; there was something about this Rudy that was different. “How Rudy got here is a mystery that has rocked his alumni network,” says one member thereof. But I have watched Giuliani since I covered his mayoralty, and I think it’s not such a mystery at all — if you understand it the right way. And that way is in basic New York City geographic-resentment terms. Giuliani and Trump versus Hillary was white-ethnic Brooklyn and Queens versus the Manhattan snoots. It’s an old conflict that doesn’t have much resonance in today’s New York — Clinton won more than 80 percent of the vote in the Queens assembly district that includes Astoria, where (on TV) that Ur-Trump-voter Archie Bunker used to live. But it’s deep in the bones of both men, and watching Trump unfurl those particular ancient grudges on the national stage seems to have energized Giuliani.

Giuliani and Trump grew up differently, sure. Trump was rich. Giuliani was working-class. Trump doesn’t fall into one of the major white-ethnic categories, namely Irish, Italian, or Jewish; but German families would have harbored many of the same ideals and beliefs — and, as the city began to “change” in the postwar era, suspicions and resentments. Nearly the same age — Giuliani is 72, Trump 70 — they watched the city deindustrialize, watched crime and the welfare rolls increase; they were young men as they saw Mayor Lindsay and his Manhattan pals side with “them,” those people to whom Trump and his father wouldn’t rent apartments, and they likely came to pretty similar conclusions.

Rudy started his career as a young government lawyer as a Democrat, barely, but moved steadily rightward, joining Ronald Reagan’s Justice Department. His stint as the U.S. Attorney in the Southern District in the 1980s altered his profile a bit because now, instead of being just a Reagan man, he was a corruption fighter taking on white-collar criminals, Wall Street con men, and the machine pols who’d been robbing the city blind. All this — especially his taking down of crooked outer-borough bosses — won him admirers among the Reagan-hating Manhattan reform swells.

But that period of détente ended, as the decade did, when he pursued the mayoralty — against the city’s first African-American candidate with a serious shot at winning. David Dinkins did beat him, by around 50,000 votes in 1989, out of 1.8 million cast. And now Giuliani started defining himself more pointedly against the elite know-it-alls.

A seminal moment here: September 16, 1992. It was known from the day Giuliani lost in 1989 that he’d be running again in 1993, so he was like an opposition leader in waiting. Tensions were exploding between Dinkins and the police, who believed, and not without justification, that Hizzoner was not their biggest fan. True, Dinkins had hired nearly 8,000 more cops to deal with the crime epidemic. But there were incidents — notably the Crown Heights riots of 1991, when City Hall’s response to the street violence was slow and confused — that infuriated the cops. Dinkins also pushed hard for a stronger Civilian Complaint Review Board, which cops despise.

Opposition to the review-board push was the proximate reason why the police held a protest rally outside City Hall that September 16. More than 10,000 officers and supporters thronged City Hall Park. This was the era before metal detectors and all that, but a barricade had been set up that day. The cop protestors broke through it. From there, according to a New York Times account, “the protest degenerated into a beer-swilling, traffic-snarling, epithet-hurling melee that stretched from the Brooklyn Bridge to Murray Street, where several politicians helped stoke the emotional fires.”

Chief among those — Giuliani. Cops chanted “Dinkins must go!” Some held racist placards or chanted racist slogans, calling Dinkins a “washroom attendant.” Giuliani took the microphone and said, his voice crescendoing: “The reason the morale of the Police Department of the City of New York is so low is one reason and one reason alone. DAVID. DINKINS!”

I spoke last week with an old Rudy hand who worked on the 1993 campaign, who reminded me to recall that day when thinking about the 2016 Rudy. “He always overdoes things,” this person said. “We were just playing to our rabid base.”

There’s a lot of talk these days about identity politics on the Democratic side, but on crime and welfare and other matters, Rudy has long used identity politics, the white-ethnic variety. He is and always has been a deeply tribal politician — it is his most authentic self.

Yet, there was this other Rudy too, a Rudy that was just as authentic. He was pro-choice. In favor of gun control. Sympathetic on gay rights, most of the time: In 1998, he signed a landmark domestic-partnership bill. He defended immigrants. Undocumented immigrants. He carried on with an executive order that Ed Koch and Dinkins had both enforced protecting undocumented aliens in the city from the reach of the federales. “If you come here and you work hard and you happen to be in an undocumented status, you’re one of the people who we want in this city,” he said in 1994. “You’re somebody that we want to protect, and we want you to get out from under what is often a life of being like a fugitive, which is really unfair.”

There was some calculation, involved, of course, in some of his positions: Peak liberal Rudy came in 1997, when he was running for reelection against Ruth Messinger and trying to run up the margin for the purposes of getting the national press to write profiles of him noting that he’d clobbered a Democrat in a five-to-one Democratic city. Even a lot of white Manhattan liberals, those old Lindsayites who couldn’t deny that the streets were safer and the city was much more livable, were voting for him now. Certainly, lots of people still hated him because of the racial conflict he seemed to revel in. But the storyline was clear, and the media consensus was universal and international: New York was back!

Then came 1998, a rather infamous year in Rudyography. That’s when, almost immediately upon having secured reelection, he started his campaign against jaywalkers. He seemed to have gone a little mad, like that revolutionary leader in Woody Allen’s Bananas, who orders the people to start wearing their underwear outside their pants.

He continued taking the cops’ side through thick and thin. When police officers shot an unarmed Amadou Diallo 41 times in the vestibule of his Bronx apartment building, Giuliani did express initial concern at the number of shots but spent the next several months saying the cops deserved the benefit of the doubt (they were acquitted). He called certain people small and sad and out-of-touch Marxists, as if in preview of his Trump alignment. But the second term was not as eventful as the first. The city appreciated his accomplishments but was exhausted by him. The universal expectation was that Rudy’s city was going to elect his leading nemesis, Mark Green, as the next mayor. He seemed, in the summer of 2001, a shoo-in. Bloomberg was a bumbler, a total rookie.

Until 9/11 happened. The mayor was so empathetic and humane. In the days after the attack, Jennifer Senior watched as he visited bereaved families and wrote up what she saw for this magazine. Giuliani sat with the parents of someone who’d died down there — not a first-responder, but someone who’d been in one of the towers — and he said to them simply: “Tell me about your son.” What a beautiful thing to say.

He semi-screwed-up in the succeeding weeks by trying to mount an argument that that November’s election should be suspended so that he could continue to serve — temporarily of course! — during the crisis. At first, public opinion was on his side. Then, after people had time to think about it, the worm turned. And Bloomberg won, largely because of a very effective ad Rudy made placing his blessing on Mike’s head (oh, and 75 million other reasons).

And so, off Giuliani went. To relax, make money, be with Donna Hanover’s successor, Judith Nathan — and get ready, one day, when the time was right, to do in real life what he’d fantasized about while standing in front a mirror as a teen in his Brooklyn home: be president of the United States.

We are about to witness something I thought we might never see again: the swearing-in of a New Yorker as president. For a long time, the Republicans were all Southerners and Westerners (Romney is spiritually a Utahan, not a Bay Stater), and the Democrats, well, they tried, not always successfully, to steer clear of the Northeast.

So it was a long shot, then, that a New Yorker like Rudy could plausibly be a presidential nominee, especially in the holy-rolling, culture-war-prosecuting GOP. The northern white ethnic may have been the electoral ally of the Dixie evangelical, but the cultural gulch was still awfully wide, the Northerner a curiosity. Giuliani and then-Governor George Pataki both had presidential dreams, but only one of them was going to make the finals, so there existed a feral competition between the two men and especially their seconds.

Giuliani knew early on that he had to do something about this. During the time period that he was running against Hillary, from 1999 until May 2000 when he dropped out, he began fashioning himself as a culture warrior. He attacked a controversial painting of the Blessed Virgin. He opined one day that it was now his fervent view that the Ten Commandments should be posted in all public schools. This view, which he’d somehow forgotten to insist on as mayor, was a comical attempt to map outer-borough resentments onto Southern Christian ones. The larger plan, described to me in late 2000 by a Giuliani associate, went like this. “Play it out,” this person said. “Say Gore beat Bush. And we beat Hillary. We defeated Hillary Clinton! … We were thinking presidency. No question.”

Life had other plans. Bush won, or became president, and so there would be no chance to run until 2008. By the time it rolled around, a lot had changed. Giuliani led the field in most of the 2007 polling — often by 20 points or more. That was the 9/11 halo. But he had one big problem, which was in fact to his credit: He was still pro-choice, and refused to change. This made his people realize that he couldn’t really compete in Iowa, with all those evangelicals, so he and his strategists decided to sit out not only Iowa but all the primaries until Florida. Many questioned this strategy. No: Everyone questioned it — six states were voting before Florida, and no one ever went oh-for-six and won the nomination. “History,” declared aide Brent Seaborn, “will prove us right.” It did not. Giuliani had trouble drawing crowds in Florida, finished a very distant third, and dropped out right after.

What do you do after that? You’re done. You go off and make a lot of money with your security-consulting business working for the pharmaceutical company that makes OxyContin in a wrangle with the Justice Department, and the government of Qatar. You give a jillion paid speeches — in 2006 alone, the Times reported, he gave 124 speeches and raked in $11.4 million. The most infamous of these have been to groups affiliated with the Mujahedeen-e-Khalq, the Iranian opposition group that was named a terrorist organization by the U.S. government until 2012 and that advocates regime change today. All that has worked nicely in financial terms — the man’s net worth today is estimated at $45 million. But none of that keeps you on the stage; you have to stay relevant.

Andrew Kirtzman, another Rudy biographer, sees the 2008 race as the great dividing line in Giuliani’s career. “It was a catastrophic failure,” Kirtzman told me. “And then suddenly, he’s making infomercials. His consulting wasn’t really to prestige clients. Some right-wing despots. The single-minded pursuit of money. From ’08 to 2015, that’s his time in a dark wilderness.”

The highest-profile relevance vehicle at hand: Fox News. And this during the Obama era, as the right was becoming unhinged by the mere sight of the man. The Southern-fried right apprehended Obama through a Biblical lens, seeing him as an Antichrist. Rudy would have seen him more through the old white-ethnic lens, with Chicago and Hyde Park being precisely analogous to New York and the Upper West Side. However different their routes, they arrived at the same destination.

Rudy’s starboard march is well crystallized in four speeches, the speeches he delivered at the Republican conventions from 2004 to 2016. The GOP held its first post-9/11 convention in Madison Square Garden. Rudy was the keynoter. He got 40 minutes. His speech was terrific. Not my flavor of tea: “Thank God George Bush is our president,” for example. But it was well-structured and smart and calculated to reach swing-voter viewers. He took shots at John Kerry, of course, but they were mostly inbounds, and he did offer up a line honoring Kerry’s military service (Rudy himself received several deferments). It was a partisan and political speech — it was a convention speech. But it had light moments, solemn moments, many colors; to return to Fred Siegel’s metaphor, it was Rigoletto, a high manifestation of the form.

Next up, 2008 — the year of John McCain and Sarah Palin. Rudy spoke the same night as Palin at the hockey arena in St. Paul. I was there. Their speeches both had the crowd rapt. The line of Rudy’s I remember most was one that was totally disingenuous coming out of this guy’s mouth, but it was funny all the same, greeted with roars of laughter. He was defending Palin. “I’m sorry,” he said, “that Barack Obama feels that her hometown isn’t” — and here he paused with perfect dramatic-effect timing — “cosmopolitan enough.” He was playing up the anti-elitism. But here’s an irony, or a contradiction, for you, and we all have them: In another way, there was no bigger Manhattan snob in the world than Giuliani. On the rare occasions he deigned to campaign in upstate New York against Hillary, he rushed back to Manhattan faster than a Lexington Avenue express train (partly, we soon learned, to see his girlfriend).

This crowd-pleasing moment highlights the one difference between 2004 and 2008 — a little more demagoguery had crept in. Whereas the hits on Kerry in ’04 had been more or less fact-based, his shots at Obama were 10 percent pettier — mocking him for being a community organizer, say. Still, the speech had a tonal range and a playfulness that helped sand down the rough edges.

Now we come to 2012, when matters take a striking turn. Now, Giuliani’s language about Obama was darker, more loaded — a “weakling,” a “disaster,” “disgusting.” The heart of the attack was an extended j’accuse about Obama trying to milk the bin Laden assassination. Giuliani did give Obama credit for ordering the attack, but then he ripped into him, charging that his administration gave the makers of Zero Dark Thirty classified material the better that they might make a film lionizing the president. “I think the way in which his administration attempted to exploit it is disgusting. I think it’s illegal and disgusting,” Giuliani said. “I think to call in people from Hollywood to do a movie about you so they have the chance to have access to classified information that puts the lives of our Navy SEALs at risk is horrible.”

The administration denied this, and no proof to support the claim has ever been adduced that I know of. In fact, at the time Giuliani spoke, the film hadn’t even been released; when it came out — after the election — Obama hardly figured in it at all. But this theory was one of those things that was whipping around the right-wing media at the time, and that, if you accepted all the right’s priors about Obama, was so obviously true that it didn’t even need “proof.” And thus did Giuliani, in that 2012 speech, cross a fateful line, from sticking with reality-based criticism to regurgitating right-wing agitprop.

Which culminated naturally in this year’s speech. It wasn’t so much that Giuliani took a long walk off a short Alex Jones-Infowars pier, though there was some of that, with respect to Hillary and Benghazi. It was that every quality that once made Rudy a compelling speaker was gone. I’ve seen him give lots of speeches — as a candidate in 1993, especially, when I followed him around all over the city; and then, budget presentations and State of the City addresses. He could cajole, he could persuade, he could inform; as noted, he could be funny.

But in Cleveland, all was buried under an avalanche of bluster and bile. Reprinting the mere words here can’t begin to convey the shocking impact of the way Giuliani shrieked them. At one point he name-checked the four Americans who’d died in the Benghazi consular attack; and he said, reasonably enough, “May they rest in peace.” But the scowl on his face as he spit out the words was chilling. At another point he called Trump, this fraudster against his “university” students and stiffer of small businesspeople and scam artist against his own “charitable” foundation, a man with a “big heart” (twice!). He “loves people. All people!” He’s just screaming now: “From the top! To the bottom! From the middle! To the side!” He was so swept up, so discombobulated, that as he said the word “top,” he bent over and pointed down below his knees, and as he said the word “bottom,” he pointed above his head.

Remember that Mario Cuomo line, about how politicians campaign in poetry and govern in prose? This was cave painting.

So that’s the journey. Once upon a time, he needed to be moderate-to-liberal on some things. Those days ended. He got insanely rich, which rarely makes people more liberal. And during the Obama years, he saw where the hard-right wind was blowing in his party, and he positioned his jib to catch it. (Although interestingly: Is he still pro-choice? I don’t think anyone’s asked him. I tried to ask a spokesman, but he didn’t respond to emails about Giuliani’s ideological journey.)

Still, something pushed him over the edge this election cycle. From the small number of old Rudy hands who agreed to talk with me (always without their names attached and usually not for attribution), a few theories emerged. First, simply, he wanted an important job, and specifically, secretary of State. Attorney general is horizontal, from Rudy’s perspective. Department of Homeland Security, he’d be similarly pigeonholed. But secretary of State! If John Kerry could do it — no; if Hillary Clinton could do it — why not him?

Also: He really just likes Trump, in addition to sharing a worldview with him. They have known each other for many, many years. Never exactly close, but they moved in the same circles and had mutual friends, like George Steinbrenner and the old limo king Bill Fugazy (both felons, by the way). For an Inner Circle skit during his mayoralty, Giuliani’s team made a video of Rudy dressed in drag as Trump pretended to be hitting on “Rudia” in a department store.

There is also the Mercer connection. Hedge-fund magnate Robert Mercer and his daughter Rebekah are heavy conservative donors. They started out being for Ted Cruz — whose conservatism Giuliani disliked strongly, I’m told — but they switched to Trump. As the investigative journalist and Trump biographer Wayne Barrett wrote in the Daily Beast, Giuliani has done legal work for the Mercers’ pro-Trump super-PAC, and law firms where Giuliani worked were paid more than $500,000 in the last two years. The Mercers also used to pay Kellyanne Conway, who worked at the super-PAC; they were big investors in Steve Bannon’s Breitbart.

And there is a deeper psychological argument: He really, really hates Hillary Clinton. He didn’t, or at least didn’t appear to, back when she was first challenging him in New York. But this year, he jumped on every Clinton conspiracy theory. “Go online and put down ‘Hillary Clinton illness,’ take a look at the videos for yourself,” he urged Fox viewers back in August, advancing the rumors of her ill health. He also once called the Clinton Foundation “a classic RICO enterprise.”

Finally, this is not quite a theory, but a factor: the death in July — 11 days before the convention speech — of Peter Powers, Giuliani’s first deputy mayor and best friend of nearly six decades. Peter was Rudy’s unsnarling face; the only guy who could occasionally pull him back from the precipice. What exact effect Powers’s passing had on Giuliani is a mystery, but it’s hard not to notice the symbolism of it all — that right after he lost his oldest and dearest friend, the man most likely to be able to talk him down, he went round the bend.

All these are plausible. But I say at bottom, he acted the way he acted because Trump vs. Hillary fired something primal in him — presented him with an obvious ally, a member of his own tribe, and a very obvious enemy. He looked unhinged to the rest of us. But to him, probably very few choices in his entire public life looked clearer.

Rudy Giuliani’s Moral Decline Isn’t Such a Mystery at All