What It's Like to Sell Political Merchandise for a Living

In red states, Bill Wyatt sells T-shirts that say "Drain the Swamp." In blue states, they say "Fuck Trump."

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Nov 15 2016, 6:57am

On the morning after Donald Trump was elected president of the United States, Bill Wyatt sat in his car in North Carolina with cardboard boxes carrying hundreds of T-shirts he could no longer sell. "History made," read one, with a screen-printed graphic of Hillary Clinton raising her arms in celebration. "President Nasty Woman" read the other, accompanied by an image of the secretary of state wearing dark sunglasses, the infamous blackberry in her hand removed.

Wyatt, a longtime political merchandiser, had spent thousands of dollars banking on the Clinton victory that so many polls and pundits had falsely predicted. In hindsight, he says he can see where her campaign went wrong: She didn't have good T-shirts.

"We tried, but she didn't give us anything to work with," Wyatt told me.

Clinton, who was criticized for appearing too stiff and image-conscious, especially when compared to her boisterous, volatile opponent, adopted the campaign slogan "I'm with Her," which was printed on T-shirts and hats for sale on her website. But Wyatt saw the endorsement, which celebrated an opposition to Trump as much as it did the possibility of the country's first woman president, as patronizing and—even worse—ineffective.

"It's like, 'I'm with stupid,'" he told me. "I mean, that didn't make any sense."

Bill Wyatt sporting two of his T-shirt designs. All photos courtesy of Bill Wyatt

Wyatt, who has owned the Los Angeles T-shirt shop Y-Qué for nearly two decades, knows a thing or two about slogans that sell. In 2002, he struck it big when he made a T-shirt bearing two now infamous words: "Free Winona." The shirt became a national rallying cry, culminating with the actor herself wearing the T-shirt on the cover of W magazine that year. (The shirt is still in stock at Y-Qué today.)

But when asked which Clinton T-shirt he designed prior to the election, Wyatt has trouble even recalling them. The graphics just weren't memorable. One T-shirt, bearing a side profile of Clinton looking like a young revolutionary with a slicked back hairdo, "doesn't even look like her," he laughed.

Another, bearing an image of Bill Clinton and Barack Obama emblazoned with the words, "I'm with her," was personally sold to Clinton's husband at a rally, according to Wyatt. "The Secret Service ran behind me, all the way back to my booth, to make sure they got the right size," he remembers. "He's a medium."

The differences between the two candidates and the ways in which they presented themselves to the American public weren't just evident on the debate stages—they trickled down to their merchandising. "[Donald Trump] had simple message slogans that people would buy and wear and promote, and she didn't really have a clear message," Wyatt told me. There was certainly nothing as memorable as "Make America Great Again," a seemingly empty yet boastful promise that became not just a mantra of the far right but a unifying fashion staple for the sea of fans sporting red trucker hats at Trump rallies as if they were sporting events.

"Think about it: The merchandising is the marketing, and everybody that gets one wears it, they advertise," Wyatt said. "It's tough when you're sitting there watching that other guy have 100 rallies, and you know, everybody's making tons of money [selling merchandise at Trump events]."

Sales weren't always this dismal for Wyatt. Back when Bernie Sanders was competing against Clinton for the democratic nomination, he sold shirts like crazy, co-opting punk rock logos from Black Flag, Bad Brains, and the Misfits, and simply replacing the band's name with Sanders's. Other T-shirts imagined Sanders as the guerrilla leader Ché Guevara, or bore grassroots campaign slogans like, "Feel the Bern" and "Bernie or Bust."

Wyatt says he sold about 2,000 T-shirts while traveling to Sanders rallies around the country earlier this year. But after Sanders lost the democratic nomination, sales slumped, and he fell into a "post-Bernie depression."

In the final weeks of Clinton's campaign, Wyatt sensed a new wave of excitement. So he packed up the blank shirts he'd initially bought for Sanders, printed them with new slogans for Clinton, and hit the road, selling T-shirts at her rally on election eve in Raleigh, North Carolina. By election night, members of his sales team were already posted at Javits Center in New York City, where Clinton's victory party was scheduled, and Wyatt had planned to spend Wednesday afternoon selling T-shirts to euphoric revelers at Independence Hall in Philadelphia.

Instead, he headed to Philly to test out the market on a new line of T-shirts and trucker hats intended to appeal to Trump supporters: "Drain the swamp," they read, a reference to the phrase Trump uses as a metaphor for cleaning out the establishment government.

On the West Coast, meanwhile, he'll continue to sell T-shirts that read, "Fuck Trump"—because there's no better way to illustrate the starkly divided nation than with different T-shirt designs. He acknowledges that his sales plan has become schizophrenic, pandering to both the left and the right, but he says it's necessary for his business to survive.

"It's not easy out there, and that's the reason why probably Trump won—because people don't have jobs, and you can't make money anymore," he said. "So if this is what I gotta do, this is what I gotta do. I don't have the luxury of just doing what I want politically anymore."

Wyatt says he has reason to be cynical about US politics. In 2004, he ran for president himself, as a Republican—partly in an attempt to take votes away from then president George W. Bush, who was up for reelection, and partly as a social experiment to see how far he could get. He landed on the ballot in five states, but became disillusioned after learning that some states do not hold primaries.

With his political career long behind him and this election in the not-so-distant past, he's looking forward to getting back to his family and his store in Los Angeles and doing what he does best: making T-shirts. He's got a Trumpacabra and a Trumpocalypse shirt in the works. And, in response to Trump's threat to arrest Clinton for using a private email server, he's got another idea up his sleeve: A shirt with Clinton's face on it, which reads: "Free Hillary."

Follow Jennifer Swann on Twitter.

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