In the run-up to Election Day, Donald Trump’s eponymous tower on Wabash Avenue had been widely viewed as a 98-story joke. Thousands of people had RSVP’d on Facebook for a “Point and Laugh at Trump Tower” event scheduled for the evening following the election, the presumption being that he would lose to Hillary Clinton. On the sidewalk along Wacker Drive directly across the river from the skyscraper, someone had set up a makeshift photo studio—a framing device that passersby could use to complete what had become the selfie du jour: a middle finger directed at Trump’s obnoxiously monogrammed building. Just last week the City Council voted to remove an honorary “Trump Plaza” sign outside the tower as a response to comments he made about violence in Chicago. The move came after a second ceremonial Trump street sign in the shadow of the building had been stolen.
Perhaps it was a sense of the presidential race as a foregone conclusion—reputable data pundits forecasted Trump’s chances at taking the White House as a paltry 10 to 15 percent—that kept Clinton supporters and protesters, for the most part, away from Trump Tower on Election Day. Less than two hours before the polls closed in Chicago, I strolled around the base of the building and was surprised to find little activity: no pussies grabbing back, no Black Lives Matter activists marching in opposition—just commuters hurrying past and tourists meandering around it. Inside, it was business as usual. Much of the first floor of the place was hauntingly empty—lobbies with ornate chandeliers but no furniture, sterile halls devoid of life. The reception area was filled with staffers and the conspicuous presence of a few stern guards in black suits and police officers waiting for an insurrection that never came.
While a Hispanic man making a delivery of food to Trump Tower was halted at the front door, I was eyeballed but not stopped for questioning. I’d worn a suit and tie, glasses, and Trump’s signature “Make America Great Again” hat as a sort of disguise. I spent the next seven hours experiencing election night at Rebar, the clownishly upscale mezzanine lounge that serves $26 fried chicken sliders and a $150 “midnight in paradis” cocktail.
Up until the time Illinois’s polls closed at 7 PM, Rebar was nearly desolate save for a handful of men that could’ve doubled as extras from The Wolf of Wall Street. As the bartenders switched the two televisions in the bar from ESPN to Fox News, more people trickled in and the place quickly turned into a pro-Trump watch party. A group of eight twentysomethings, all in matching “Make America Great Again” caps, grabbed a table in the back. An apparently inebriated man in a blindingly white suit jacket, his long red hair peeking out from under his own Trump hat, accused me of being a secret Clinton operative.
“You’re sure you’re not? I recognize you,” he said, his breath stinking of whiskey.
“Not me,” I said.
“Ah . . . well, you look like the guy. It’s your teeth. Very similar.”
Throughout the night, he tried starting chants of “Fuck the media!” and “Hillary for prison!” neither of which caught on with the rest of the bar.
Not everyone was so zealously pro-Trump. A man visiting Chicago from Ireland was puzzled by the American political system. “You’d be much better served with a parliamentary system,” he said. And then there was Dan, an amiable business traveler from rural southern Illinois staying at Trump’s hotel while in town attending a conference at McCormick Place. “I don’t care about the social stuff,” he said. “Both candidates are bad there. For me it’s about jobs and foreign policy, and I think Trump’s a little better there.”
Still, even a grudging Trump voter like Dan got caught up in the Election Day moment as the Donald racked up electoral votes and the gathering at Rebar continued to swell. When Fox News’s Megyn Kelly called the state of Ohio for Trump, Dan and dozens of others pumped their fists, exchanged high-fives, and chanted “Trump! Trump!” A muscle-bound man wearing a skin-tight “Trump/Pence 2016” T-shirt warned me to watch my laptop—he was about to pop a bottle of champagne once President Trump became official.
The scene developing at Trump Tower caused me to flash back to Wrigleyville on the night of the Cubs’ stunning World Series victory. (Team Trump, coincidentally, was also supported by the Cubs-owning Ricketts family.) While the celebration in the streets around Wrigley Field was communal, the Rebar gathering felt like a small, hermetically sealed bubble of Trump love in a sea of Clinton support.
The figurative ninth inning of Election Night stretched on too long. Results from Pennsylvania and other key states were slow to come. Rebar stopped serving alcohol at midnight, after which the staff turned on the house lights. But a few dozen patrons remained to hear Trump’s victory speech as I made my exit, descending the curved staircase past more bored-looking security and Chicago police. As I slipped into the revolving glass door that lead out onto the quiet city streets, a doorman bid me good night.
That “Point and Laugh at Trump Tower” event? It’s been converted into an “Emergency Protest” intended to “resist the outcome” of the election.
This morning I returned to Trump Tower to see what, if anything, had changed now that Trump’s highly mockable presidential bid had become a sobering reality. The selfie stand was gone. A lone redheaded woman stood outside the building holding a sign that read “Hate will never win.”
I gazed up one more time at Trump’s shiny skyscraper. It almost seemed to be flipping the middle finger right back at Chicago.