'Be prepared': Olivia Nuzzi soared from ambitious Middletown teen to tussles with Trump

Art Gallagher was running a popular Jersey Shore politics blog, “More Monmouth Musings,” when he came across another local blogger whose work raised an eyebrow.

He didn’t know anything about Olivia Nuzzi. Nobody did, really. But he could tell she had talent.

“I thought she was hilarious and smart and gutsy,” Gallagher said. “And I thought my readers would enjoy that.”

With the intention of offering Nuzzi space on his blog as a guest columnist, Gallagher set up a meeting at a coffee shop in Red Bank. Then Nuzzi walked in, and Gallagher nearly fell out of his chair.

“I was shocked — she was like 16,” he recalled. “And I was like, ‘What the hell am I doing here with this high school junior?’ With the way she presented herself and how smart she was, I thought she was in her late 20s.”

When his head stopped spinning, Gallagher made a spot decision whose long ripple effect eventually would reach the White House.

“OK, I don’t care,’” Gallagher told the Middletown resident. “As long as it’s OK with your parents, let’s do it.”

Thirteen years later Nuzzi has become a force in political journalism, a 30-year-old rising star with New York Magazine whose exclusive and sometimes jarring interviews with Donald Trump, Rudy Giuliani and others have shaped national discourse.

Everybody comes from somewhere, and Nuzzi’s origin story is a reminder for would-be mentors of the virtue of giving someone a chance.

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Created a monster?

Nuzzi grew up in the River Plaza neighborhood of Middletown. She attended Middletown High School South for a few months, then switched to independent instruction as she pursued a different path.

“I was in acting school in Philadelphia,” she said by phone last week. “I wasn’t very good at traditional school stuff. My parents were really accepting of that.”

A few subjects did capture her attention.

“I knew I was very interested in politics and I knew I was very interested in writing,” she said. “I wanted to work with words in some capacity, but I didn’t have a sophisticated idea of how those interests might converge.”

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Enter Gallagher.

“I thought it was very cool he took me so seriously intellectually,” she said. “Looking back, I wouldn’t have taken me that seriously.”

On paper, in retrospect, Gallagher seems an unlikely champion. He’s conservative — he currently handles publicity for Toms River’s Republican mayor, Mo Hill — and Nuzzi has held up an unflattering mirror to Trump’s inner circle. Her 2019 piece about her meeting with Giuliani described the former New York City mayor as drooling onto his sweater, with an unzipped fly and three cell phones he hardly could operate. Her recent New York Magazine cover story on Trump compared him to the washed-up silent-film star in the classic movie “Sunset Boulevard,” a parallel Trump all but draws himself in his interview with her (Trump subsequently lashed out at Nuzzi as “a shaky and unattractive wack job”).

Does Gallagher, with his deep-rooted Republican credentials, think he created a monster?

“She makes me laugh and she makes me proud,” he said. “She’s got such a gift for expressing the absurdity in the things she observes.”

In an information ecosystem filled with silos for the like-minded, Gallagher said, "Discourse is important. I have relationships with people I don’t see eye to eye with (politically). We enrich our lives when we engage with people we don’t agree with.”

What would Gallagher do if Nuzzi came calling for Toms River’s mayor, or any politician he advised?

“I would not advise anybody to not talk to Olivia,” he said, “but I would advise them to be prepared.”

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'The potential to be even bigger'

Nuzzi didn’t stay with “More Monmouth Musings” for long. An early column caught the eye of Dan Jacobson, publisher of triCityNews — a weekly publication that covers Asbury Park, Long Branch and Red Bank. In 2011 he called Nuzzi and offered her first paid writing gig — a monthly column at $50 a pop.

But first, he had one question for her.

“Your résumé doesn’t say where you go to college,” Jacobson recalled himself saying. “She said, ‘Dan, I’m in high school.’”

Just like Gallagher had before him, Jacobson paused for a moment.

“I thought back to when I was a senior in high school and adults gave me a chance to do advanced stuff,” he said. “I said, ‘Tell you what, why don’t you send a sample piece on anything you want?’”

Nuzzi’s sample column was a dud. She’d overthought it, trying to impress Jacobson. He could have cut ties right then. Instinct told him otherwise.

“I said, ‘Olivia, write like you talk. Just be real,’” Jacobson said. “She sent it back and it was perfect. It was her voice, and that’s the voice you read today.”

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Jacobson’s advice has echoed through the years.

“He positioned my brain in a different way,” Nuzzi said. “I sort of feel like he set me up at the gate and I took off charging from that moment.”

In letters of recommendation for college (Nuzzi attended Fordham) and internships, Jacobson would write, “I expect big things from Olivia.”

He still does.

“If this is the level her career reaches, it is so impressive and I am so proud of her, and proud of the role I played,” Jacobson said. “But she has the potential to be even bigger.”

How big? Someone, he thinks, who could one day moderate a presidential debate.

“She clearly is at that talent level,” he said.

A note above the desk

Nuzzi loved growing up along the Bayshore, and although her parents are deceased, she still comes back to visit her brother Jonathan, who is raising a family in the Lincroft section of Middletown. She misses the food here, especially the pizza. Although she inhabits a different world now, with appearances on CNN and interviews in the Oval Office, Nuzzi appreciates her roots in the field.

“I’m so lucky I encountered people who were so generous to me and really had so much care about working with me,” she said.

In the ultimate tribute, Nuzzi hangs a long-ago note from Jacobson above her writing desk.

“Here’s $50 for your first article,” it reads. “Let it always be known that I was the first one to pay you for your writing.”

Jerry Carino is community columnist for the Asbury Park Press, focusing on the Jersey Shore’s interesting people, inspiring stories and pressing issues. Contact him at jcarino@gannettnj.com.

This article originally appeared on Asbury Park Press: Political journalist Olivia Nuzzi started as ambitious Middletown teen