NYC Pt 2: TRESPASSING TRUMP'S CHILDHOOD HOME
Our New York tour of Trump's boyhood home was Olivia's idea. What we had planned to cover got postponed, and Denise had to return to California a day early for her daughter's graduation, leaving us with an unexpected content gap. June is hectic that way, juggling work and kids; our plans kept changing by the day.
For those not familiar with Olivia's work, it should be noted that she is something of an expert in Trumpology. She has a long history of tracking Donald. She's been in the mix for over a decade now — from the White House to the courthouse — watching and writing about the guy. Her first feature was published back in 2014. Years later, she drew Trump's ire for calling his world “small,” after an insider confided that the magic at Mar-a-Lago was “gone.” The sobering insight poked a pin in his inflated post-presidential façade. Afterward, he lashed out in retaliation, calling her, among other things, “dumb as a rock.”
“Former President Donald Trump attacked New York Magazine reporter Olivia Nuzzi as an ‘unattractive wack job’ late Monday after she wrote last week that Trump is largely holed up at his Mar-a-Lago resort — even quoting an insider as saying “the magic is gone.”
“The reporter was a shaky & unattractive wack job, known as ‘tough’ but dumb as a rock, who actually wrote a decent story about me a long time ago. Her name, Olivia Nuzzi. Anyway, the story was Fake News, her ‘anonymous sources’ don't exist (true with many writers),” Trump said.
Nuzzi reported that the 45th President has not ventured beyond his two Florida resorts — Mar-a-Lago in Palm Beach and Trump National Doral Miami — since he announced Nov. 15 he was running for president for a third consecutive time. “He just goes, plays golf, comes back and f–ks off. He has retreated to the golf course and to Mar-a-Lago,” Nuzzi quoted one source as saying. “His world has gotten much smaller. His world is so, so small.” — New York Post
At lunch the day before, Olivia laughed recalling the litany of insults Trump has hurled at her over the years under a variety of circumstances, some of which she temporarily included in her Twitter bio. For instance, her shaky hand — a trait that naturally caught Trump's attention and which he later mocked — was merely the result of nerves. She was a young, up-and-coming reporter interviewing Trump in the Oval Office, under the intimidating presence of his suited entourage, and Mike Pence hovering over her shoulder while she took notes. The scene, the way she describes it, sends a chill down my spine imagining myself in her shoes – especially at that age.
Instead of taking an Uber, Olivia offers to drive us — a rare treat in New York, where confident drivers are few and far between. Our field trip cohort consists of Olivia, Link, Denise, and myself. The drive gives us an hour to catch up and get acquainted, during which the buzz of Manhattan dissolves into a panorama of steel and glass. From the backseat, it all unfolds with cinematic allure — a living diorama of ambition traded for the well-tended greenery of Queens, where the blend of old manor houses and bustling markets offers a soothing alternative to the city's incessant pulse. We pass an elderly couple on a park bench, a street musician unloading instruments from their trunk, a wood-planked fruit stand, and an ancient oil shop with faded, hand-painted window advertisements.
If you view Trump as I've come to — a Gatsby-esque character at the center of a self-invented, gold-encrusted empire — his childhood home only reinforces that image. Nestled in a sun-soaked enclave of the Jamaica neighborhood in Queens, the house is much smaller than I expected, with paint peeling off wood-planked window framing. It’s a slight shock at first, if only because it goes against everything we've come to know and expect from the 45th President. Nothing about it is terrific or tremendous. It is earnest, overgrown, and overtly neglected; and yet even in this state, it still possesses an unsettling charm.
Walking up to the front door, I find a disconnected water notice taped to the window. Pressing my face to the glass, I laugh out loud, spotting a life-size Trump cutout propped in the corner of an otherwise empty room. As if that wasn’t enough, a haunting black and white portrait of him from the ‘90s hangs on the wall. I call everyone over to see it.
“Who lives here?” I wonder aloud, delightfully confused by such an odd detail. Even in its dilapidated state, someone loves Don enough to keep him as part of the house’s decor.
Trump's father built the Tudor-style house at 85-15 Wareham Place where we are trespassing. A towering figure in New York real estate, Fred Trump notoriously transformed the landscape of Queens and Brooklyn with his innovative, affordable housing projects. His disciplined and ambitious legacy flourished amid stately homes and manicured lawns, profoundly influencing his son. Growing up, Donald, his fourth-born child, often accompanied his father to construction sites, where he gleaned invaluable lessons in business dealings and financial negotiations. Meanwhile, with elegance and steadfast discipline, Mary Trump, a Scottish émigré, ensured that her children remained grounded as the Trump name grew in wealth and prominence. “My father taught me the value of hard work,” Donald noted in The Art of The Deal, “and my mother instilled in me the importance of staying grounded and focused.”
According to those who knew him, young Donald was always a vibrant bundle of ambition. His mother described him as a self-motivated boyhood entrepreneur, collecting empty soda bottles for extra coins and constructing model skyscrapers from toy blocks, dreaming of the towering buildings that would someday dominate the New York City skyline. “I always loved building things,” Donald has been quoted as saying, reflecting on an early interest in architecture.
When the hint of a teenage rebellious streak emerged, he was sent to the New York Military Academy. The decision was meant to channel his energy and focus into leadership and discipline. It worked. Donald thrived there, becoming a student leader and captain of the baseball team. “Military school taught me discipline, focus, and how to lead,” he later remarked.
As Fred flourished in real estate, the Trumps consciously maintained local investments by continuing to contribute to community projects. Despite an increasingly demanding work schedule, Fred stayed actively involved in local philanthropy, donating land for projects like the YMCA. “My father believed in giving back,” Donald noted. Growing up in the diverse environment of Queens, he said, taught him to mesh with all kinds of people. “Queens was a melting pot. It taught me how to connect with people from all walks of life. Queens was where it all started, where I learned to think big and never settle for less.”
Since its 2020 listing, the home has seen varied market activity. Shortly after being listed, it was rented out for $4,000 a month, despite initial neighborhood concerns about its upkeep. In 2021, attempts were made to auction it off again, and a crowdfunding campaign emerged to purchase it as a gift for Trump supporters. The outcome of these efforts remains elusive.
As we explore the property, signs in the front warn against taking or feeding the kittens that have taken over the premises. Of course, this only makes me want them more. I don’t even like cats, but I can't help but fantasize about sneaking a tiny cat with a miniature Trump toupee into my suitcase as a souvenir for Hayes. Given our ongoing mouse problem at home, a Trump-approved feline might be just the solution.
Sensing that my curiosity is inching towards an illegal activity, Olivia and Link split, while Denise and I indulge our sister motives and wander around to the backyard, where we find a gardener on the neighboring lawn watching us with a smile, as if expecting tourists in blazers and heels to find him there. He doesn't question us. Unprompted, I confess that we are looking for an unlocked window to squeeze through for an interior tour of the house. He smiles, pointing to the upper story where Baby Donald’s room was, encouraging our trespassing. He says the cameras on site are old, merely props. We could get in without any trouble.
When asked if Trump should hire a gardener to clean up the grounds, he says, “Who wouldn't want to work for the guy?” He’s a fan of Trump and predicts a big win come November, but resents that someone from Trump's team hasn’t sent a gardener over to clean up the yard. When pressed on the issue, the weeded overgrowth appears to genuinely depress him.
Around the side of the house, Denise discovers a window loose enough to enter. Thrilled by the discovery, I encourage her to climb through. She’s halfway in, her lower half dangling, when Link and Olivia walk up and gasp in horror. “I didn’t sign up for this!” Link exclaims. Respectfully, no one should be caught forcefully entering a former president's home. Its Twitter fodder waiting to happen, and Link knows it. He disappears in a flash, Olivia trailing behind him — but a beat slower.
“We can't do this in front of them,” I tell Denise, helping her out of the window. Under the shade of a rusted awning we briefly debate intrusion. She argues that it’s what our followers expect, that it's on brand. “Plus, your hair looks great, which is always a top consideration when risking a mug shot,” I add.
For us, these kinds of antics solidify street cred with MAGA diehards — Lord knows they love a mug shot. But dragging new friends (renowned journalists) into illegal activity could be damaging to their reputation.
After a few minutes of back and forth, trying to determine what's morally sound, we decide to leave without entering. We wander back to the front where I suspect Link and Olivia are considering ditching us — rightfully so.
To my surprise, they haven’t. We all get back in the car and drive towards our next destination.
Day Trip To Jamaica Queens
“Some people think of Trump as some kind of a genius mastermind. Like, “Oh, I want to distract from this, I’m going to pick a fight with Jim Acosta today, and that’ll help me.” I think he’s much more instinctual that that. It has always felt like, “Oh, my God, he’s turning this into theater and we are all a part of it and doing the dance exactly how he wants us to.” It sometimes felt like he’s pressing play on this choreography that ends up unfurling exactly as he thought it would.” — Olivia Nuzzi via Slate.com
"My mother had a sense of the grand. I can remember her watching the coronation of Queen Elizabeth and being so fascinated by it. My father had no interest in that kind of thing at all."— Donald Trump
On our way home, Olivia drives us by Fordham University. We stroll briefly through the campus, past graduates and their families post-ceremony. I wonder, watching them, what they think — or if they even know — about their famous alumnus.
After high school, Donald Trump began his college journey at Fordham in the Bronx, later transferring to the more prestigious Wharton School at the University of Pennsylvania. Graduating in 1968 with a degree in Economics, he set his sights on real estate.
At Wharton, he focused intently on his studies and his future, often traveling back to New York to assist his father with booming real estate projects. “I was always thinking about business,” Trump said in an interview. “My father taught me that real-world experience is just as important as academic learning.”
Reflecting on his college years, he emphasized the blend of education and practical experience that helped define not only his career but his outlook on life. “Wharton gave me knowledge, but working with my father gave me street smarts.” This combination, or at least what he gleaned from it, propelled him to become one of the world's most recognized figures in modern history — the most loved and hated man of our time.
It’s not hard to imagine that Fred Trump would appreciate his son’s bold, if chaotic, ascent into the global zeitgeist. Thinking big hasn't failed him yet.
Love the snaps! Of course the kittens sign is adorable! At least we get a real glimpse of Trump’s former digs, and not the illusive Greek Jewish Puerto Rican Black ghetto that Biden imagines… 😉
I read the room wrong - I thought Link (omg - I love him so much) would have been a look-out for you and Denise. and/or joined in.