• Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.

Andrew Giuliani is test-driving his father's legacy in New York

·16 min read
In this article:
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.

NEW YORK - Andrew Giuliani is easy to spot marching through Queens in a St. Patrick's Day parade. He's the one wearing the "Team Trump" warm-up jacket and blue baseball cap with large letters across the front: "G-I-U-L-I-A-N-I."

Andrew is here to gather signatures he needs to get on the Republican ballot for this year's governor's race. The crowd, however, is chanting a different name.

Subscribe to The Post Most newsletter for the most important and interesting stories from The Washington Post.

"Ru-dy! Ru-dy! Ru-dy!"

Just ahead of Andrew, trundling along in a golf cart, is his father, Rudy Giuliani. The former New York mayor puffs on a cigar as he shakes hands, kisses cheeks and otherwise basks in the affection of his long-ago constituents.

"I love his father. Is that the son?" Joan McDonald, 90, a retired clerical worker, asks as she eyes Andrew, 36, who has Rudy's full cheeks and saucer-wide grin.

"We need you back - promise you'll be behind the scenes!" Donna Blonder, a retired teacher, tells Rudy.

Blonder, like many Americans, watched the November 2020 news conference in which Rudy claimed a massive voting-fraud conspiracy while a black liquid that appeared to be hair dye trickled down each side of his face.

The former mayor, then working as President Donald Trump's personal lawyer, had taken a major role in trying to undo his boss's election defeat, an effort that led to Rudy having his New York law license suspended for making what a committee of judges described as "demonstrably false and misleading statements to courts, lawmakers and the public at large." (His attorneys have said they would challenge the finding.)

Blonder tells Rudy he looks better now than he had at that news conference, after which his dye-stained visage became a national punchline. Rudy hugs her.

"Ah, we all make mistakes," he says, cackling. "Just make sure you vote for my son. I know how good he'll be."

Political dynasties are a well-worn American tradition. The Adamses, Roosevelts, Kennedys and Bushes are among the clans that have spawned second generations of torchbearers and wannabes. What makes Andrew Giuliani's quest distinct is that he started his political career at a moment when his father's reputation has never been more damaged.

Rudy's behavior has inspired head-shaking among his own former advisers and associates, as well as Trump allies. In a recent memoir, William Barr, Trump's last attorney general, called the legal effort to overturn the election results "a grotesque embarrassment." In Washington, a House select committee has subpoenaed Rudy as part of its investigation into the events on and around Jan. 6, 2021, when pro-Trump forces tried to block the certification of President Joe Biden's victory.

Yet, in certain sections of New York - conservative White enclaves in the city, suburbs and beyond - the Giuliani brand is still strong. And while some Republicans running statewide in Blue America might want to avoid touting their ties to Trump and Rudy, Andrew Giuliani celebrates them at every turn.

"When we talk about the best in politics," Andrew says in an interview, "I look at a Rudy Giuliani in New York in the 1990s, and I look at Donald J. Trump in Washington.″

He's hoping that their political legacies are not as toxic in New York as some might think. At the same time, his prospects are widely viewed as dim in a state where registered Democrats far outnumber Republicans and the GOP establishment is backing a different candidate.

On the stump, Andrew's rhetoric is Trumpian boilerplate: He mocks "leftist" newspapers, statehouse "socialists," mask mandates, transgender rights activists and Biden's Supreme Court pick Ketanji Brown Jackson. As for the 2020 election, he echoes his father, saying he has "major concerns" about the integrity of the results. Asked if he regards Biden's election as legitimate, he says, "Does he even know he's president of the United States? I would love to ask him the question to see if he can answer lucidly."

Just like dad, Andrew is running as a pro-cop, law-and-order Republican. He rails against New York's recent move to allow people charged with misdemeanors and nonviolent felonies to no longer have to pay cash bail. The reform is intended to ensure that the poor don't have to wait in jail for a court date while others can pay their way out.

"There's a playbook for going after crime," Andrew said in a recent appearance on Rudy's radio show, on 77 WABC. "It's called the 'Giuliani Playbook.'"

Yet it's an open question whether the Trump era might have compromised the Giuliani name as a foundation for a political dynasty. There are Republicans who hoped Andrew would run for something, maybe a legislative seat, that seemed more appropriate for a newbie.

Rudy was not among them.

"That's sort of the old way," the former mayor said. "I think he's ready."

Andrew became famous for imitating his father.

It was 1994, and Rudy had just won the mayor's race with a tough-on-crime campaign. At a swearing-in ceremony on the City Hall steps, a 7-year-old Andrew mimicked his dad by raising his right hand and then shaking the judge's hand afterward. He then exchanged a handshake with Rudy and turned to the microphone. "Thank you," Andrew told the crowd, as if the cheers had been for him all along.

The moment inspired national debates about proper parenting - not to mention shtick on "Saturday Night Live," where Chris Farley played Andrew.

His antics were fodder for more headlines 14 years later at Duke University, where the golf coach cut him after alleging several transgressions, including a claim that Andrew had thrown an apple at a teammate's face with such force that it "exploded," according to the school's answer to Andrew's breach-of-contract lawsuit. (In his complaint, which was dismissed by a judge, Andrew said he had "tossed the apple at the teammate, glancing off the side of his face"). He managed to play pro golf anyway, clocking a tournament win in 2009, but the biggest payoff of his time on the links is that he developed his relationship with Donald Trump.

When Trump won the presidency, Andrew got a job in the White House's Office of the Public Liaison, helping coordinate visits from sports teams. He also served in a less official role: presidential golfing buddy. He was promoted to special assistant to the president, reportedly at a $95,000 a year salary. At the end of his term Trump appointed Andrew to the council overseeing the U.S. Holocaust Memorial Museum in Washington. They still play golf when Andrew visits the ex-president at Mar-a-Lago.

"I consider him an adviser in my life," Andrew says.

During his presidency, Trump was someone whom Andrew says he felt free to tell "what I honestly thought, and that didn't necessarily line up with everybody's agenda."

Pressed for details, he says, "It's protected by presidential privilege - executive privilege, right?"

Andrew says he had no role in planning the "Save America" rally on Jan. 6, 2021, but that he walked the short distance from the White to the Ellipse, where it was held, to see Trump and his father speak. At that rally, Rudy hyped the idea that Trump's loss had been due to "fraudulent" ballots and "crooked" machines. (Rudy's attorneys have unsuccessfully sought to derail defamation lawsuits filed by Dominion Voting Systems and Smartmatic, a voting technology company.) After the Ellipse, Andrew says he returned to the White House, where he watched the Capitol attack on television.

"Obviously, you don't want to see people trespassing in the Capitol," he says.

His White House stint technically qualifies as government experience, but to impress voters who value the savvy that comes with years of public service, Andrew has gotten creative. When he announced his campaign last June, he said his political experience stretched across "parts of five decades" - suggesting that he was counting backward to Rudy's first mayoral campaign, in 1989, when he was 3 years old.

That was the first iteration of the multigenerational Giuliani roadshow: Rudy brought Andrew along on campaign swings, sometimes pausing the caravan to allow the boy out for a few minutes to scamper about. His rambunctious presence delighted advisers, who put him and his little sister, Caroline, in television ads to help soften the image of the candidate, then known as a scowling prosecutor who locked up corrupt politicians, insider traders and mobsters.

On his own campaign trail, Andrew Giuliani is a caffeinated, J. Crew version of his often dour father. He locks eyes with voters as he beams and shakes their hands, ever-ready to extend an emphatic thumbs-up as they swoop in for selfies.

"He treats people like mosh pits," said Curtis Sliwa, the Guardian Angels founder and recently defeated Republican mayoral candidate, who is supporting Andrew and is often by his side. "He is better at it than his father was."

After the Queens parade, the Giulianis and their entourage retreat to a hole-in-the-wall cigar lounge in Bayside called Harry's Habana Hut. Rudy settles into a club chair with a stogie while someone pours Jameson into red cups.

"This is like a small version of parliament," Rudy says, admiring the seating.

"I would do a debate here," Andrew says.

Someone asks the former mayor how Republicans would fare in the upcoming midterm elections.

"Politics is so weird," Rudy says. "You always have to predict it with a certain amount of humility."

Danny Beck, 52, a firefighter in his dress uniform, wanders in. When he sees Rudy, he freezes.

"Oh my God - no way!" he exclaims. "This is a f---ing dream. Can I get a picture?"

"With that uniform on, you can get whatever you want," Rudy says.

As a tool for drumming up attention, the enduring value of the Giuliani name is obvious at such moments. In the broader picture, the costs are also hard to miss. There are plenty of New Yorkers who recoil at the name.

"It's Giuliani fatigue," says George Arzt, a public relations consultant, former City Hill reporter and press secretary for Mayor Edward I. Koch. "When people think about Andrew, if they remember, they think about the kid fooling around at the inauguration, and the dye running down his father's sweaty face."

A March poll from Siena College found that Republicans in the state viewed Andrew more favorably than unfavorably while voters were less familiar with his GOP opponents. But New York voters viewed Andrew unfavorably by a 2-to-1 margin.

Despite his relationship with the Giulianis, Trump has not made an endorsement in the race. The New York Republican Party, hoping to mount a unified effort against Democratic Gov. Kathy Hochul, has embraced Rep. Lee Zeldin, whom Trump has supported in the past. At the party's convention last month, the congressman received 85 percent of delegates' votes; Andrew Giuliani captured less than 1 percent.

Gerry Kassar, chair of the New York State Conservative Party, said he thinks that Andrew initially did well in polling because of a "misunderstanding' about who was in the race. "People were asking me, 'What's the deal with Giuliani?' - they thought it was the father running and then they realize it's the son," Kassar said. "At that point, they hear he's 36 with not much experience and they don't understand why he's running."

Kassar said voters "enjoy meeting Andrew," but he described his candidacy as "more of a media creation than a reality" that inspires nostalgia for when his father was mayor. "It's like the history channel," he said. "But right now we're in the present."

Zeldin also has a major cash advantage, with more than $5.6 million in the bank, according to January campaign finance reports; Giuliani had less than $200,000. Andrew's biggest donor appeared to be Jimmy John Liautaud, the sandwich-making tycoon and a Trump supporter. Liautaud and his wife, Leslie, gave Andrew $136,658.

His donors include Alan Placa, the priest and lawyer who helped Rudy get his first marriage annulled on the grounds that his wife was his second cousin. (Placa, who officiated Andrew's wedding, gave $100. Reached by The Post, he didn't want to talk about it.) There's also Arnold Gumowitz, the New York City real estate magnate, who met Andrew a decade ago when the young man was dating his lawyer's daughter.

"I didn't think he had it in him," says Gumowitz, 93, recalling when Andrew told him he was running. "I said to him, 'What makes you think you can run?' He started telling me what he could do, and I was stunned by his ability to describe and speak out with great force and attitude."

Gumowitz gave Andrew $47,100, according to campaign finance records. He also gave Hochul, the Democrat, $69,700.

Rudy said in an interview that he likes that Andrew is running as an insurgent candidate, but encountering resistance frustrates the man who was once the city's premier power broker. He says he was "pissed" when a once reliable ally, the Staten Island Republican organization, endorsed Zeldin and would not even interview Andrew.

"I'm insulted by it," Rudy said. "They owed me at least an interview for all I've done for them."

At the cigar lounge, where the Giuliani crowd was sharing the bottle of Jameson, someone says, "Can we top off the mayor please?"

After finishing his stogie and drink, Rudy stands up and says, "I gotta go find my son so I can help him."

Outside, Andrew is smoking his own cigar, talking about tax reform and collecting more signatures. Rudy emerges, and the two of them, after posing for more photos, wander into a tavern packed with St. Patty's Day revelers. "Now listen up," shouts Mike Turck, a retired detective, when the former mayor walks in. "His son is gonna be the next governor, all you schmucks!"

The Giulianis find seats at a back table, where they eat corned beef and talk about Andrew's decision to join the family business.

"He wanted to be a cop, then he wanted to be a football player," Rudy says, recalling his son's early interests. The idea to run for political office came only recently.

Eventually, Rudy has to go. Andrew stands up, kisses him on the cheek and says, "Love you, call you later."

They haven't always been this close. Rudy and Andrew's mother, Donna Hanover, went through a contentious divorce that began when Rudy, then mayor, abruptly announced at a news conference that he was leaving her. In 2007, after Rudy remarried and was running for president, Andrew told the New York Times that he was having a "little problem" with the new Mrs. Giuliani, and that he and his father had gone awhile without speaking.

And these days?

"My father is one of my best friends," says Andrew, waving away questions about whether Rudy's recent troubles are a campaign liability. "I'm as proud now of my father as I've ever been."

Asked if he's ever critical of his father, he says, "We're Italians. It stays in the family."

If the Trump era bonded the Giuliani men, it seems to have left them at odds with two other family members. Andrew is receiving no help in his campaign, at least publicly, from his mother and sister.

When asked if she was supporting her son's race, Donna Hanover, through a spokesperson, said: "Andrew has been a very loving son to me and I love him very much."

Caroline Rose Giuliani, 32, a Los Angeles-based filmmaker, authored a 2020 Vanity Fair article entitled: "Rudy Giuliani Is My Father. Please, Everyone, Vote for Joe Biden and Kamala Harris." Reached by phone about her brother's campaign, she said, "I don't have any comment."

Asked about their roles in his campaign, Andrew says he wants his mother to focus on "great quality time" with his 4-month-old daughter. His sister, he says, "is a great person."

The morning after the parade, Andrew Giuliani drove to the Bellmore train station on Long Island, where hundreds gathered to meet and greet Republican candidates in a parking lot jammed with pickup trucks and festooned with Trump flags.

"Is this the AOC rally?" Andrew jokes as he emerges from an SUV, not waiting for it to fully stop before jumping out.

Posing for a photo with a woman, he chortles and says, "If I was Andrew Cuomo, I'd be in trouble right now."

"I'll never forget you from your father's inauguration," Steven Lichtenstein, 60, a financial adviser, tells Andrew. "I knew you'd be a leader."

After the Republican candidates assembled onstage, Andrew grabs an American flag and waves it for the crowd. A woman in a white coat sings the national anthem.

A car pulls into the lot. Jacqueline Monte, 49, eyes the passenger in the back seat, a man she considers a hero. She struggles to compose herself. "I, like, want to cry right now," she says.

Out steps Rudy Giuliani.

The former mayor is led to the stage, where an organizer hands him the mic.

"I'm gonna introduce my son, Andrew," he says, before beginning a 21-minute monologue in which he mimics Vice President Harris as a slow-talking simpleton who describes Russia as "big" and Ukraine as "small"; fantasizes about prosecuting the Biden family; asserts that liberal philanthropist George Soros is a "sick man"; and praises his son for being unafraid to publicly celebrate "my friend and my client" Donald Trump.

"How about America's mayor?" Andrew Giuliani says, taking the mic from his father.

Prowling the stage for 15 minutes, Andrew trashes mask mandates, describes Cuomo and Hochul as "dictators," promises to repeal bail reform, and shouts, "Stop the war on cops!"

Then the man who entered politics as a toddler mentions his own baby daughter.

"She made a promise with me," he says. "She shook my hand, and I said, 'I'm your only boyfriend until you're 25 years old.'"

"So I have changed the diapers, I have looked under the hood," Andrew continues. "She's a woman. It's gonna be the last guy in a long time who looks under the hood, right there. But guess what? She was born a woman and she's gonna stay a woman - it's that simple."

The crowd roars.

"Make New York great again!" Andrew Giuliani shouts.

As he and his father depart, the crowd's cheering turns into a chant.

"Ru-dy! Ru-dy! Ru-dy!"

Related Content

Turns out Aimee Mann is really good at painting, too

Kyiv comes back to life with a mix of sorrow, dark humor and triumph

Mykolaiv region on edge amid fear of a new Russian offensive