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Infiltrating Trump Tower with filmmaker Alex Winter

Trump Tower has become a fortress—one that is technically open to anyone.


Dell Cameron


Posted on Jan 20, 2017   Updated on May 25, 2021, 4:14 am CDT

Since the election, President Donald Trump has spent most of his nights in his 57-story tower on Fifth Ave. in New York City.

During peak hours, as many as 25,000 pedestrians walk past the building, where the U.S. Secret Service and local police have erected high-speed crash barriers and a series of checkpoints to rival even the busiest U.S. airports. New York City has spent an estimated $500,000 per day to secure Trump Tower. Due to the added fortifications, foot traffic to the midtown businesses that reside below the mirrored skyscraper has slowed to a trickle, causing as much as $40 million in economic damage.

The landmark, where Trump and his family live on the top three floors above some 260 apartments and 13 floors of commercial offices, has drawn visitations from politicians, bankers, celebrities, and tech entrepreneurs.

“Just after the holidays I flew to New York and spent a long day and night shooting in and around Trump Tower with my crew,” says filmmaker Alex Winter, himself a New Yorker, who put together a montage of various happenings at Trump Tower.

Winter recently produced a short film, Relatively Free, about Texas-based journalist Barrett Brown, documenting his first taste of freedom—or first Big Mac of freedom, anyway—since he was first incarcerated in 2012.  

“After the election, I felt somewhat helpless,” Winter says. “Other than furiously writing and calling my state reps and taking to the streets, I felt compelled to do something filming around Trump’s win and the utterly surreal world we suddenly found ourselves in.”

Using archival footage in addition to footage of the tower shot by his own film crew over a full night and day, Winter describes the atmosphere at Trump Tower as an “overtly tense and weird vibe.”

“Technically speaking, Trump Tower is open to the public,” Winter says, “but in actuality, it’s now like Fort Knox and I knew they’d never let a full crew in the building. So the first order of business was to get myself inside and shoot what I could as surreptitiously as possible on my iPhone.”

“It’s now like Fort Knox.”

Before entering the building’s lobby, Winter passed through two security checkpoints: One at the street corner on 57th avenue, and a larger one that resembles a TSA checkpoint just past the lobby entrance. Asked by police his destination while on the street, Winter quickly blurted out: “Starbucks,” referring to the coffee shop just inside the lobby. “Miraculously that was all it took to be granted access, so at the much larger second checkpoint, I repeated my lame destination with a little more conviction and voila!”

The police officers inside the building—swarmed by tourists, Secret Service agents, and a cadre of spiritless press—appeared tense, he says. “Needless to say, this is a security disaster, and I couldn’t wait to get out of the place,” Winter says. He spent an hour shooting footage inside building before meeting up with his crew to capture the exteriors and the ambient noise emanating from the streets and the tower itself. It all went off without a hitch—except for the flash mob protest they were caught in, and having their pictures taken a few dozen times by security.

“I’ve been photographed by law enforcement before, but this time it was something of a relief,” he says. “After all the president-elect was yards away, tucked inside his penthouse, in the heart of Manhattan’s busiest tourist district, being visited by some of the most powerful people in the world. What could possibly go wrong?”

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*First Published: Jan 20, 2017, 12:46 pm CST