Magazine | August 29, 2016, Issue

Trump Tourism in Hillary Country

Deep in the heart of a deep-blue city, hugging a bright-green river, there rises a massive, gleaming hotel that bears the name of Trump. The letters, which spell out the Donald’s last name, stand an almost comical 20 feet high, forming a gloriously tacky belt on an otherwise good-looking skyscraper. The city is Chicago, that great midwestern sprawl of big shoulders, fevered Democrats, and a cluster of architecture buffs forever peeved at what one prominent critic called “Trump’s self-inflicted urban acne.”

Twenty sixteen is full of ironies, and so it is that I, a decidedly non-Trumpian Republican, came to stay at this decidedly Trumpian fortress during the week of the Democratic National Convention. True story: Within approximately two minutes of our entry into the building’s soaring lobby, the good people at the Trump International Hotel and Tower Chicago gave each of my children a hat.

Good heavens. How did I let this happen? The journey began last year, on an earlier Chicago trip, when one of my aforementioned children literally fell through the floor of a shady discount condo rental procured through Airbnb. While my son was downright delighted with this development — “Mommy,” he declared, wide-eyed, one leg submerged in a rogue air vent haphazardly covered with something resembling tin foil, “this apartment has secret passages!” — I was not.

And so, for our next trip, I swung the other way, finding a quasi-acceptable deal on a Trump hotel suite that I assumed (correctly, it turns out) would have no holes in the floor. I promptly booked it, about a year before the hotel’s blustery namesake would snag the GOP nomination for president. The Trump phenomenon, in other words, was barely a twinkle in the mischievous universe’s eye.

To be fair, the Trump hotel’s hats were gray, not red, and they said “Trump International Hotel and Tower,” not “Make America Great Again.” My oldest son, who is growing impressively proficient at subtle forms of torture, promptly donned his hat, beaming. “Hey, Trump can’t be all bad,” he said, tromping into our admittedly very nice room. Trump Chicago is not the infamous Trump Taj Mahal, which for years was reportedly held together by a few strands of twine hastily gathered from the seediest corners of the Jersey Shore. In fact, my stay at the Trump Chicago was largely enjoyable.

One night, the staff left us a giant bowl of caramel and cheese popcorn, and I grudgingly ate it all. I heroically managed to stop anyone in our party from opening the room’s bottle of “Bling H2O,” which came in a promiscuously bedazzled bottle and likely cost $565.95. The only mishap came when the room’s hair dryer, a machine that apparently had a good sense of humor, suddenly stopped blowing hot air.

“You’re either staying at a Trump, or in the shadow of one,” the Trump Chicago website booms. On a rainy Wednesday, I found myself in the shadow of a giant gray Trump International Hotel and Tower umbrella, which, as you might imagine, makes for an awkward accessory in downtown Chicago. I shuffled down Michigan Avenue, sheepish, trying to decide the best way to hide the Trump logo. Twirled to the front? Twisted to the back? Alas. Every few blocks, I heard various mutters of “Hillary!” A homeless man, busy shouting something terrifying about vaccines, paused to give me a dirty look.

But it is a strange animal, this surging American political polarization. The next night I took in a show at the Second City, the famed Chicago comedy house that for decades has served as a pit stop on the way to outlets such as Saturday Night Live. If anyone from the Donald Trump campaign is reading this, I have some unusual advice: You could do worse than to send a busload of on-the-fence Republicans to a show at the Second City. 

There are three types of leftists in this world: the happy leftists, the melancholy leftists, and the angry leftists. This third group is unquestionably The Worst — and unfortunately, it also dominated the stage during my time at Second City. There were huffy jokes about abortion, surly jokes about Christians, haughty jokes about Texas, jokes I couldn’t repeat without at least three NC-17 ratings, and, of course, various perfunctory and self-congratulatory jokes about Donald Trump.

The smugness would have been fine, really, if the ideas behind it had been fresh, not moldy progressive tropes. It also would have been fine if the cast had exhibited even the tiniest sliver of good-humored recognition that maybe, just maybe, Hillary Clinton is terrible, too, the political equivalent of a charred-fire-ant sandwich served with a vat of long-expired Jalapeño Cheddar Bugles dangled over one of those dramatic Indiana Jones booby-trap snake pits. Sadly, this did not happen. Maybe they forgot that part of the show. Hey, at least they served wine.

Two friends from Texas joined us in Chicago, and they were lucky enough to miss the show at Second City. They did not, however, miss one particularly long and painful Uber ride piloted by a passionate Hillary Clinton supporter. As we rolled along, the radio blasted the harsh-edged, quietly desperate strains of the former secretary of state’s perfunctory DNC speech. “She’s going to be president!” our driver crowed, turning the volume up.

Outside the car, the 20-foot Trump sign loomed. Inside the car, Hillary droned. “I’ve got to get back to Texas,” one friend whispered. Up in the front seat, our other friend was quietly cracking — and at the next intersection, he suddenly leapt out of the car. He ran across the street, arms thrown back into the night air. It was glorious. He was free. For a moment, we were all free.

Heather Wilhelm is a National Review Online columnist and a senior contributor to the Federalist.

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