My 12 Hours Hanging out with the Hustlers at Trump Tower


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My 12 Hours Hanging out with the Hustlers at Trump Tower

Since Trump Tower has become an unlikely locus of world power, it's attracted all manner of salesman, dreamers, and naked cowboys.

It took about an hour of standing outside of Trump Tower for me to see someone smile, which was odd considering how many people were having their photo taken. Japanese tourists posed stoically in front of its jagged facade, then were shuffled along by cops and replaced with similarly unhappy-looking Midwesterners thumbing their noses and solemnly, dutifully cataloging the memory.

Like me, these out-of-towners found themselves drawn to the gaudy, sky-scraping phallus that became a somewhat unlikely locus of world power on November 9. Trump Tower had been a destination ever since its namesake made the unlikely transition from reality TV star to full-blown political movement leader, but when he became the president-elect, a selfie in front of the tower became a can't-miss New York souvenir. The foot traffic on that stretch of New York City's Madison Avenue was already intense, but the ensuing fervor (and the security that came with it) led a small army's worth of beat cops, counter-terrorism units, and secret service agents being deployed at a daily cost to the city of about $1 million, according to a November CNN report.


But I didn't come to Trump Tower for a quick pic. I wanted to know what sort of person is drawn to it—the type of person who doesn't just stop by to check it off a list that includes the Empire State Building, Statue of Liberty, and 9/11 Memorial but instead spends hours hoping to catch a glimpse of Donald Trump or one of the generals and billionaires he's appointing to top cabinet positions. I wanted to rub elbows with the entrepreneurs, media folks, Trump fanboys, and protestors who had become tower regulars.

All photos and GIF by Jason Bergman

Anyone can come see Trump Tower for themselves. Despite what the police barriers suggest, it's not closed off to the public––the pageantry of the K9 units and security checkpoints seems designed to merely minimize the amount of people loitering near the entrance. Although my press badge provided one excuse to get inside, a civilian couple came in behind me by saying they wanted to get some hot chocolate at the Starbucks in the tower's food court.

Kit and Margaret, who hailed from the Virginia suburbs, didn't stay long, though. They thought New York City was a fine place to visit every once in a while, but it was way too chaotic. And as the Naked Cowboy––Times Square's most famous street performer, whose description is in his name––ran past them in the lobby, they realized that the scene at TT was perhaps not for them. I headed to the Trump Grille, where the 45-year-old was nursing a vodka with a splash of orange juice.


For the uninitiated, the Naked Cowboy, a.k.a. Robert Burck, is a guy who's been standing in Midtown Manhattan with a guitar over his dick since 1998. And for the past 73 days, he's been coming to Trump Tower at around 11:30 in the morning. He says that he relishes the opportunity to meet influential people like senators, but the main draw seems to be that he can drink at a real bar before working instead of in a parking garage.

Here's how his day goes: Have a drink at Trump Grille, then head up an escalator to the Trump Bar, which apparently has nicer seats. After he's sufficiently lit up, he takes his schtick outside to take advantage of the tower crowds before taking his act back to Times Square around three. None of this is to say that he doesn't also completely adore the president-elect. Trump reminds Burck of his father, who, he says, has been on his village council for 30 years, has served as a volunteer firefighter, and dutifully changes his 98-year-old mother's diapers every morning.

"He's an All-American big strong white man," Burck said of Trump. "Not that he has to be white, or that he has to be a man. He's just a winner."

Although years of busking have weathered his face and physique, the guy still draws plenty of admirers, like a woman named Tracie, who was getting a headshot autographed when I pulled up a stool between them. Burck was also trying to pawn off a Naked Cowboy bobblehead to the bartender so that she could re-gift it to her boss. Burck, who also just launched an oyster company, explained the artfulness of this deal: "He buys my drink. You save money. I save money."


Tracie told me she lived in Georgia, but had a business consultant husband who often worked in the area. That week she joined him, and was glad she did, because that's how she ended up drinking a mimosa a few feet away from the Naked Cowboy, who was more than happy to flirt back despite being married to a woman he referred to as "an illegal from Mexico City" who he later showed me a picture of to ensure me she wasn't fat.

Trump Tower

Deciding I shouldn't get in the way of what might transpire between the day-drinking maybe-lovebirds, I headed back up the escalator and into the lobby where there are pens of media people and civilians standing and watching the golden elevators, hoping to catch a glimpse of someone famous and yell something at them. In the civilian corner, a man named Pier openly laughs at a (OK, admittedly lame) protestor reading quietly aloud from The People's History of the United States.

"Don't mess with Donald Trump," Pier yelled, like the human embodiment of the people who reply to Trump's tweets. "Hillary Clinton, most corrupt trash in the world. Get me away from these people––they stink!"

The 77-year-old had Willie Nelson hair, a Donald Trump shirt, and a Super Mario accent marred from a former habit of smoking three packs a day. Every day he commutes from North Bergen, New Jersey, in a Russian military motorcycle with the hope of speaking to Trump. In a past life, he was a construction foreman who earned the nickname Animal. Although he now walks with a cane, Pier aspires to build the border wall, and cites his credentials as being a ruthless taskmaster who speaks Italian, French, Spanish, and a little Arabic.


"I used to fire like flies," he cackled. "Smoking a cigarette? 'You're fired, you son of a bitch.'"

Pier wanted to show me pictures of his children, whom he had a habit of describing as "good looking motherfuckers." He kept trying to pull up their Facebook pages on his phone, but kept being rebuffed by a prompt from the IvankaTrump wi-fi network. After I helped him navigate the technology, he asked me to help turn his life story into a screenplay and insisted on exchanging phone numbers. When I decided to get lunch, I left him tapping at his screen and muttering to himself about Hillary Clinton.

NYPD officers stand guard at Trump Tower

I decided to try the Trump Bar this time, but was told that it was closed despite being full of diners and drinkers. At first I thought I was being gaslighted by the employee, but when I headed back to the Trump Grille with hopes of getting the infamous taco bowl, I was told that everything was in the process of closing for a private event.

The only place that remained open was the press area, a human zoo of my hard-working colleagues hunched over keyboards and spilling each other's coffees. At this particular moment, the goal was to shout questions at Satya Nadella of Microsoft and Sheryl Sandberg of Facebook after they left a meeting with Trump. (This was Wednesday, when Trump was hosting meetings with leaders from the tech industry.) Although no one responded, and the reporters didn't get their quote for the day, they kept at it. What else was there to do?


As my stomach grumbled, I had a thought: Holding a bunch of reporters captive in your gilded tower is a pretty good business strategy. There were about 60 journalists and camera people there, and it costs about $30 to eat two meals at Trump Grille. Multiply that for every day between the election and inauguration, and that's… well, look, I didn't come here to do math. Point is, as Trump has learned over the years, getting a lot of people's attention pays pretty well.

At about 4 PM, well before some of the more famous attendees of the meeting departed, members of the media were asked to leave. I lingered for a bit inside the barricade, pretending to shop for jewelry at the adjacent Tiffany's, where diamonds are advertised as things to "collect during life's most meaningful moments" and watches are described as "treasured symbols of a lifetime." Pretending to be rich was also a stalling tactic; I hoped to stumble into someone like tech titan and lawsuit funder Peter Thiel when I headed back out into the cold. Unfortunately, almost all of the fanfare from the daytime had dissipated and I was met with an almost-empty street. I also had a voicemail from Pier asking me to come to his hotel room: "I hope you call me sometime. Bye-bye!"

Meanwhile, a changing of the guards had occurred across the street. The sole liberal protestor I had seen in the morning was replaced with one that a cop described as "the resident crazy" to the other cop taking over her shift. A couple of guys normally hawk comedy club tickets on the street had set up shop selling anti-Trump pins for $3 a pop. One of them, Paul Rosa, who was covered in oddly placed patches for bands like Rush, said they'd been doing this for about seven months after protesting and realizing they might as well make some money for their efforts. Now, he claims that the side gig is lucrative enough to be a full-time job.


Two lonely conservatives stood holding an American flag decorated with Trump-Pence stickers. One of the flag-holders was busy telling a gay man why he should prefer Trump to Clinton, which gave the other man––an Israeli––the opportunity to tell me in broken English that he was getting paid. When I pressed him to find out how much he was making, he suggested instead that his fetish was having women yell at him. (Ultimately, I couldn't tell if he was joking about either of these things.) He flashed a mischievous, bone-chilling grin as a woman passed by and spat, "Shame on you!"

By then, the night had turned freezing cold. I tried to go inside the Abercrombie & Fitch but was smoked out by the stench of whatever fragrance those stores fill themselves with. I leaned against the facade and was soon approached by David, a 23-year-old who worked at a private equity firm that invests in technology start-ups. His Trump-supporting grandmother had worked at Sak's Fifth Avenue her whole life and lived a couple of blocks away. He was on his way there, but despite not having a hat or a scarf, found himself lingering near the tower. He's a celebrity-watcher, too, the kind of person who tells strangers about their sole encounter with an A-lister a few minutes after meeting them. We talked about Justin Long finding his phone in a cab. He showed me the selfie they took together.

But after a little bit, he got to the real reason why he was mesmerized by the tower. David is from Virginia and is still registered to vote there; the Democratic incumbent in his congressional district ran unopposed this year. Since then, David has realized that he'll be 25 soon and that he should just run next time as a Republican, even though he isn't registered as one and voted for Clinton. None of that matters, he said, this election proves it. What's important in politics is likability, salesmanship––David said he can sell anything to anybody, run in any circle. For instance, he says "y'all" convincingly and often enough that people think he was raised in the South even though he's basically a product of the Northeast. He studied finance and political science in college, so he likes to think he knows a little bit more about this stuff than the average citizen. Hell, maybe he can even become president someday.

"If he could do it, anyone can," David told me. "All he did is smile and say basically nothing." Then he pulled out his phone to take a shot of the tower for Snapchat.

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