On the Campaign Trail With Andrew Giuliani

The Son of Rudy is working out his father issues on the road to Albany.

Andrew Giuliani in May. Photo: DeSean McClinton-Holland
Andrew Giuliani in May. Photo: DeSean McClinton-Holland

Andrew Giuliani was holding a silver spoon. He just was. There’s no getting around it. Sitting in a booth at Mansion Diner on 86th and York — about a thousand feet from each of the two homes in which he was raised: his mother’s apartment and Gracie Mansion — he poured a thimble-size packet of Farmland whole milk into his third cup of coffee and used the symbolically charged but otherwise ordinary instrument to stir. “New York means something to everybody,” he said. “It evokes a reaction.”

Ten days earlier, the Son of Rudy had announced his campaign for governor on the grounds that New York needs a Giuliani restoration to recover from the other dynastic Andrew — and that he can achieve it by scaling his father’s blueprint for the city of the ’90s to address the needs of the entire state in the ’20s. “I think the name Giuliani evokes a reaction in most people, too,” he said.

If the reaction most people had throughout the witching era of the last presidency was the thought What happened to Rudy?, then these early days of post-Trump Trumpian politics are animated, at least in New York and Palm Beach and certain parts of New Jersey, by a related concern: What the fuck is Andrew doing? As one person close to Donald Trump put it, “That’s a question that a lot of people who genuinely like Andrew and genuinely like the mayor are asking.”

It’s rich, a Trump associate suggesting that another candidate’s pursuit of office is ridiculous. A country may not be the sum of whom it elects, but a party is no more or less than its nominees — making Giuliani’s run a test of what “unqualified” means to the Republican electorate now. Giuliani, who is 35 years old, spent his early childhood on the Upper East Side, attended prep school in a tony Jersey suburb and college in North Carolina. Fully a third of his official campaign biography is devoted to his good grades at Duke (where he majored in sociology), a few internships in finance and real estate, his time as a “surrogate relations” volunteer on the Trump campaign, and his marriage. He cites as qualifying work experience his stint as a professional golfer; the four years he spent in the Trump administration, where he served in the Office of Public Liaison and as a special assistant to the president; and the seven weeks he was professionally a pundit on Newsmax, a network for people who think Fox News is too moderate, before he quit to join the gubernatorial race.

But he does have the last name. And his very own MAGA-ish slogan, complete with exclamation point: “Bring Back New York!” The biggest problem, for Giuliani, is that the MAGA candidate had already been anointed by the time he entered the race. Lee Zeldin, the representative from New York’s First Congressional District, who announced his run in April, was well liked in Trumpworld even before he committed the greatest official act of obedience available by objecting to the certification of the 2020 election results on January 6, hours after a violent mob stormed the Capitol and threatened to hang Vice-President Mike Pence. The second biggest problem is that Giuliani appears to have miscalculated the value of his personal relationship with the ex-president.

Giuliani told me that over three or four conversations, Trump expressed support for the idea of a run for governor. “He said, ‘Giuliani versus Cuomo, that’s a heavyweight fight. You’d sell out the Garden with that,’” Giuliani said. Then he complimented Trump’s physical appearance, as other politicians hoping for an endorsement sometimes do, on the understanding that Trump reads his own press and appreciates appeals to his vanity: “He looks like he’s in fighting shape right now. He looks good. He looks like he’s probably in the best shape that I’ve seen him in in five, six years.”

But Trump is not happy with what Giuliani has been telling the press about their relationship. “The president did not encourage him to run. They had a friendly conversation, he likes him, but he did not tell him to run,” the person close to Trump said. “His appreciation and high regard for Rudy is probably impacting his decision to respond or not respond to slightly inaccurate claims made by Andrew.”

And then there’s the problem of the party. Republicans haven’t won a statewide race since 2002, but Governor Andrew Cuomo is newly vulnerable. “It seems like a very foolish expenditure to have a primary which will do nothing but drag candidates as far to the right as they can get,” Nick Langworthy, the state Republican Party chairman, told me. He doesn’t want to blow this because of a pesky democratic process that pits Giuliani, Zeldin, and former Westchester county executive Rob Astorino, who has also declared, against each other. Such a distraction might allow the wounded governor to escape with a fourth term in 2022. “It’s a waste of donor funds and candidate energy fighting amongst ourselves when we could be focused on November.”

When Giuliani first expressed interest in the race, he was met with “skepticism” and “curiosity,” according to one Republican official. Everyone may know the name Giuliani, but it’s been 20 years since the end of his mayorship and a decade-plus since his failed presidential campaign, and few conservatives involved in state government have any connection or debt owed to Rudy. As for Andrew: “He’s not someone who’s ever been a part of the New York political fabric. He’s not a New York political player. He had no New York political relationships,” the official said. “And then there’s his lack of overall experience in the workforce. ‘Mock’ would be too strong a word, but people are ridiculing him.”

In fact, Cuomo may be the only New Yorker who wants Giuliani in the race. “The more clowns that get into the clown car, the better,” a person close to the governor said. “The Republican field in New York is just like a menagerie of the absurd, and Andrew Giuliani may well be the ringmaster.”

Photo: DeSean McClinton-Holland

Like many villains and politicians, Giuliani has a vaguely unsettling quality. His hair and skin are a similar shade of muted strawberry blonde. He looks like Rudy only when he smiles, and he sounds like him only when he yells. He talks in cliché. “In this day and age, politics is front and center,” he told me. When he charms, it’s often premeditated. Upon his announcement, he was roasted for saying he’d “spent parts of five different decades of my life” in politics (reminder: He is 35), but the remark was part of a Buddy Hackett–style shtick he’s developed for public settings. He tried some of it out at Mansion Diner. “Career politicians are generally not my favorite,” he said. Beat. “I’m worse.” Beat. “I’m a politician out of the womb.” Beat. “I get up in the morning and I try to wash the filth off of me.” Beat. “And it’s still on!”

He’s also worked on more serious lines that attempt to absorb some of his father’s political achievements. “I think about all of the New Yorkers who have their lives today because Rudy Giuliani decided to step in that arena, because Donna Hanover stepped in that arena with him, and I take a ton of pride in that,” he said, referring to the decline in violent crime in the 1990s. “I’m my father’s son.”

It wasn’t always so. Rudy wrecked his marriage to Hanover badly enough that he had to move out of Gracie Mansion. “It didn’t feel that abnormal to have that stuff come out in public, probably, as much as it should have,” Giuliani said. Rudy married his mistress in 2003; the kids took their mother’s side; and for long stretches of Andrew’s life, he barely spoke to his father. During the 2007 Republican presidential primary, Andrew confided in the media. He told the New York Times that he had “a little problem” with his then-stepmother, Judith. Even now, a lifetime and two divorces later, Rudy is not in the 12-member family group chat that includes extended Giuliani relatives and close friends, according to Heather McBride, Andrew’s former babysitter, a member of the group chat who now serves as his spokeswoman. She remembered Andrew as a happy child, though the stress of his strange life manifested in painful ways. Andrew chewed his fingernails severely; once, he landed in the hospital with an infection, and McBride recalled how, when she visited his bedside, he asked her to bring kid-contraband in the form of a Coke. (When I asked Hanover to comment about her son’s campaign, she gave a statement that you may notice does not contain any reference to her son’s campaign: “Andrew has always been an incredibly loving son to me and I love him very much.” Rudy, for his part, didn’t respond to interview requests.)

Rudy first used Andrew as a prop soon after his January 1986 birth. In court, while prosecuting a New York Democrat on corruption charges (and plotting a campaign for mayor), he “paraded” his newborn son “before the jury,” according to the defendant. Andrew said he could remember campaigning as a 3-year-old. A few years later, when Rudy won, Andrew hammed it up at his inauguration, which inspired a savage parody from Chris Farley on Saturday Night Live. He was 7. He is the only son of a famous politician I know of whose relationship with his father is so strained that people volunteer — with no insult intended — that other men in his life have been “father figures” to him: Donald Trump (news, perhaps, to Don Jr.) and Peter Powers, Rudy’s first deputy mayor and McBride’s father.

Powers was a giant in New York Republican politics in the Giuliani years and a giant in Giuliani’s life. Powers died in 2016, and it was at his funeral that some Rudy allies first noticed what they refer to as his “decline.” McBride recounted an incident during Rudy’s eulogy. Addressing the mourners, Rudy said he had a message from Powers to Heather and her sister. His dying wish, he said, had been for them to take care of … a woman who was not their mother. “My sister and I pinched each other. It was one of those moments where you’re like, Do I sit here and half-smile, or do I stand up and — I don’t even know what I would have said,” McBride told me. It was “shocking,” she said. “I’m not mad, it was just odd.” The experience made her admire Andrew more, she said, because he’s spent a lifetime demonstrating “composure” in scenarios like that one. Before Rudy was a source of shame for America, he was a source of shame for people who loved him.

Of course, Andrew doesn’t see it that way now. “It’s public that my dad and I haven’t always been on the best terms,” he said. But self-interest has a way of mending bonds. “If I didn’t use him as an asset, as an adviser, as somebody who I’d rely on, I’d be foolish.” After federal agents raided Rudy’s home in late April, amid an investigation into his dealings with Ukraine, it was Andrew — not an attorney or spokesperson — who addressed the press on the street. “He’s a tough guy. He can take anything,” he told me. “And what he knows is he’s got his son backing him.” I asked how he gets ahold of his father, since his many phones were seized in that raid and, Andrew said, hadn’t yet been returned. “Carrier pigeon,” he deadpanned. “There are a lot of them in New York State.”

The post-Trump era, as the post-Nixon era, has been welcomed as the “return to normalcy.” But normal is not a state to which you can come home; we cross its shifting borders as we negotiate the world, and each time we arrive there is the first time. One piece of normalcy Giuliani has going for him, it would appear, is his marriage. Beginning with a 2017 story about their engagement the previous year, the New York Post gossip grande dame Cindy Adams devoted generous space to romantic bulletins about “handsome” (her word) Giuliani and “beautiful,” “blonde,” and “Lithuanian” Zivile Rezgyte, whom she cast as the kind of immigrant around whom simple patriotic lore, and modern far-right marketing and self-deception, is spun. “To find the American dream,” Adams wrote, “she arrived 10 years ago with $300. Spoke no English. Had zero advantages. Now a US citizen, she’s a pro in real estate. They met at Derek Jeter’s final Yankee Stadium game.” As far as origin stories for political spouses go, that’s good shit. Semi-exotic. Mostly familiar. Easy to adapt for a stump speech or TV spot. Good for the generic candidate or the MAGA candidate, and good specifically for Giuliani, since it acts to quell, somewhat, the desire to bludgeon him with that silver spoon.

But at least part of the story Giuliani fed to the Post appears to be untrue. Public records show that Rezgyte was a licensed real-estate agent in Chicago as early as 2002 — placing her in America well before the tabloid timeline. By the time she would have been arriving, impoverished, in New York, according to the Post’s account, public records show that not only was she already here, she already owned a co-op in the West Village. A former employer said she worked in real estate in Queens for most of that missing decade. Giuliani wouldn’t answer questions about the discrepancy on the record. “Andrew says Cindy Adams’s account is accurate, and he’ll leave it at that,” McBride said.

Hating on some clueless trust fund jackass for having the gall to suggest he should be making decisions for others on a scale larger than a bachelor party is an exercise that often transcends partisan ideology. When a son of privilege seeks political power, it often seems that entitlement offense rages brightly in the moments just before private acceptance or approval kicks in: Parts of the population are reminded on a psychic or genetic level that they yearn for monarchy, while other parts decide they like the comfort of continuity under the guise of a democracy. The other form of entitlement, maybe a bit less galling, is assuming a right to patience and attention, to the willingness of a public to serve as an audience before which to work out familial psychological trauma. When I sat down with Andrew, it was the eve of Mercury’s retrograde and, he noted, his father’s 77th birthday (a Gemini, of course).

“There’s pain and daddy issues that exist beneath this,” one longtime Rudy associate said. A second longtime Rudy associate was gentler: “What Andrew is doing is less about Rudy than it is about what Andrew is doing to process Rudy.” There is something uncomfortable about Giuliani’s campaign. If you watch him for long enough to ask what might compel a person to do a thing like this, you get the sense that the act of running is one of self-harm, of lashing himself in the void left by his father. Is he out to prove something to Rudy or to show him — show us — what being Rudy’s son has done to him? Does he subconsciously want to hurt Rudy? You can’t tarnish a legacy that’s already been shattered, then lit on fire, then burned to a heap of ash, then sprinkled into the swamp and dissolved into a toxic vapor. Or can you?

When pressed to explain why he’s running a race he’s not just unlikely to win, but unlikely to get far enough to even have an opportunity to really lose, Giuliani says something like, “I think we have the best chance to win.” This is pure hunch. He cites no polling. No data. Just vibes. But you can’t sustain a campaign — pay staff, buy ads, keep yourself on the road — for an entire year without funding. Giuliani insists that part is going well, but numbers for the quarter won’t be filed until next month. Quietly, party officials hope that the anemic figures they predict from Giuliani will be enough to convince him to put his young campaign out of its misery.

It’s not a big operation yet anyway. Few of his father’s protégés are still hanging around looking for work as operatives or chances to prove loyalty to their has-been ex-boss. And so it’s run by one Rudy veteran, Jake Menges; McBride, an ex–News 12 correspondent who is still really a reporter at heart; Ryan McAvoy, a Trump White House functionary best known for once leaving a copy of his encrypted passwords at a D.C. bus stop; and Sean Kalin Jr., a TikTok-famous zookeeper from Florida who loves sloths and kangaroos and whose father competed on a golf-themed reality show with Andrew in 2013.

Woven throughout Giuliani’s script are facts about New York State that sound new to him, like he’s reading from flash cards or marketing copy from the tourism board. With practiced excitement, he told me about the “beautiful” Finger Lakes region as if he’d just gotten back from a space exploration. “New York is also the fourth-largest agricultural producer as a state,” he said. (According to the Department of Agriculture, it’s 25th.) And he made this almost heroic rhetorical leap while discussing how he could compete with Cuomo’s ample war chest: “We start with $1 at a time. It’s been great to see where people, not just in New York, but all across the country, have been donating from. And I think what it shows me is New York is what I believe it to be, which is, it is the state that connected the world to the rest of America. When you think about the Erie Canal, that’s what it did.” About this he was astonished, or aping astonishment for my benefit: You’re never gonna believe it! The lake goes to all these other fucking lakes!

As we wrapped up at the diner, he got back to the Big Message. “My dream in doing this is not to be a politician, it’s to really help the 19.5 million New Yorkers that I know deserve better,” he said. “That’s what inspires me really, more than anything. The glory, or getting the you-know-what kicked out of you — I’ll let other people analyze that.”

He smiled and thanked the waitress. Soon, he would take off for foreign lands north of Yorkville, where he would be trying out the act. “I don’t know,” he said. “Maybe I’m just a glutton for punishment.”

On the Campaign Trail With Andrew Giuliani