Arcana 5:

Elizabeth Kleinman's Interview with Presidential Candidate Andrea Shepherd for In-Depth Magazine

BRINGING IT ON: ANDREA SHEPHERD ON THE FINAL DAYS OF HER UNEXPECTED ROCK STAR PRESIDENTIAL RUN

Written by Elizabeth Kleinman

Published in the October 2028 Edition of In-Depth Magazine

Andrea Shepherd is having a busy month. 

A year ago, most Americans had never heard the name, save perhaps for the small but fervent Illinois following that got Shepherd elected to congress in 2026. Despite her modest fame, anyone who met her could immediately tell she was magnetic, articulate, and smart. Though in talking to her Chicago constituents, there’s perhaps one more quality that endeared her to them. 

“I’m a loudmouth,” Shepherd says with a bit of a laugh. “I talk fast, I talk loud, and if something needs to be said, I say it. But it’s to be expected. I’m a New York girl who fell in love with Chicago, I wasn’t going to come out soft-spoken and dainty.” 

Dainty is hardly a phrase that anyone would use to the describe Congresswoman Shepherd, it’s true. At almost six feet tall, she’s the tallest person in a lot of the rooms she walks into. Her eyes are intense, her hands calloused. “That’s the bar rot,” Shepherd jokes when she spots me eyeing the tough skin of her hands. She spent almost four years’ worth of nights tending bar at Logan’s Square, while by day did she worked for the ACLU. “I did little but work for a lot of my twenties and my early thirties.” She stops to glance at a nearby iPad, which is currently showing her schedule. “Not that anything’s changed that much on that particular front…” 

We caught up with the eleventh hour Democratic candidate for president before a rally in Columbus, Ohio. She’d only be in the State for a little over six hours total, flying in between a lunch with big campaign donors in New York City and a show that magician and long-time friend Amy Stirling is doing in support of the campaign in Seattle. This is - Shepherd’s taciturn campaign manager Joseph Musa tells me while the candidate takes a phone call - all things considered a fairly manageable day. During the really busy days, she might do as many as five events in a day, including town hall-style forums that have been known to go on for over three and a half hours. Still, grueling as the schedule is, the campaign’s growing momentum is impossible to deny. The Columbus rally was expected to attract over twenty-thousand attendants. The final tally was closer to thirty-five thousand. 

Shepherd grew up in Syracuse, New York. Her family was from humble means, although the candidate describes it, as usual, in more colorful terms. “We were middle class, but just barely. We were in that place where you get taxed like you’re middle class but when you’re living it? It really doesn’t feel middle class.” Her father was a high school history teacher, while her mother owned and ran the bar that was the informal headquarters for half the unions in the town. 

“It started off as just the local teachers’ union, but in time everything from steelworkers to nurses ended up meeting there. It got bad enough that mom eventually put up a little calendar on the wall and had everyone sign up for slots.” She grew up around people that loved their work, loved to help others, and loved the idea that they were stronger together than they were apart. Oftentimes, these discussions would spill over into the Shepherd home itself. “Three, four, sometimes five nights a week I’d come home to a room full of people talking about some problem they had at work, or that someone they knew had at work, and going, ‘How are we going to solve this? How are we going to work this?’ That’s home to me. That’s a pair of fluffy slippers and an ice cold drink at the end of a long day.” 

Amidst the hustle and bustle of their work and their tireless support of local syndicates, Mr. and Mrs. Shepherd still found the time for a dedicated spiritual life. Although even there, there was a bit of unorthodoxy. “My father’s Christian, my mother is Jewish,” Shepherd says with a small shrug. “I grew up going to church with him and to synagogue with her.” She waves away both questions about any tensions this caused during her youth and about whether she now identifies with one faith over the other as an adult. “That’s never been the point, to approach it with this lens of… one of these is right and the other is wrong. I believe in God, if that is what you’re asking, but I also believe that one of the greatest gifts my parents ever gave me was having two separate perspectives on how to worship.” 

This blurring of religious lines is just one of many things that Andrea Shepherd is asking America to get over. Among the others: if elected she would be America’s first female president. Falling just barely within a few months of the minimum qualifying age, she would also be its youngest president. She would be the first president since Grover Cleveland, all the way back in the Nineteenth Century, to go into office without a spouse. “Yeah,” Shepherd says with another glance towards her schedule, “I somehow never quite found much time to dedicate to my dating life, not sure why…” 

Shepherd’s campaign has done little to try to mitigate these factors, flying in the face of much conventional political wisdom. “Back in the early days of the campaign, this big shot political strategist we brought in from D.C., he said that I needed to get a boyfriend. He’d even come up with a list of guys that we could come to an ‘arrangement’ with, men that would make me more electable. It’s the only time I have ever fired someone on the spot.” An amusing anecdote, but one that begs the question: does Shepherd think that she’s actually electable? “Look,” the candidate responds after a moment’s pause, “end of the day? Some people are just never going to vote for a thirty-five-year old, single, black woman. They’re just not, and there’s nothing I could say or do that would get them to budge. Every minute I spend trying to convince them is a minute I don’t spend getting the people who are actually maybes to come around to yes. That’s all there is to it.” 

It’s the kind of answer I’ve grown to expect after covering the Shepherd campaign for the better part of three months. She has a way of being direct and blunt in everything from matters of environmentalism to LBGTQ rights to - perhaps most divisively - the shortcomings of her own political party. “I was born in 1993, man,” she says when I asked her about that last point. “Democrats have done some good things in that time, but for every step forward there’s been so much capitulation. So much acting like horrible ideas had merit in the name of reaching across the aisle. So much watering down the basic, most bare-bones ideas that we should be defending and articulating. I’ll give credit where it’s due, but that’s gotta cut both ways, and especially given recent revelations of corruption within the party? I think we have a lot to demand of our so-called leaders.” 

Given her distaste for the Democratic Party, why run from within it? Why not forge her own path as an independent? “I considered it,” Shepherd admits, “but I ultimately decided that I could do more good from within the machine. An independent is too easy to ignore, too easy to write off as an extremist. When you’re a member of the party and your message resonates with their audience, you can actually move the conversation forward. And end of the day, where the conversation goes is so much more important than where you go.” 

She has pithy answers in the chamber for practically every major question that has come up ever since the tide started to turn in her direction. Isn’t she too young to be running for president? Isn’t it, strictly speaking, not her turn? “The idea of turns in politics is absolutely deranged. This isn’t a law firm, there isn’t a corporate ladder, there’s no such thing as seniority. You articulate the ideas that you believe the Party stands for and you defend them to the best of your ability. If your version is the one that finds purchase, then you’re called on to serve. It’s as simple as that.” 

What about her lack of experience? “Absolutely. I’m not done learning how the government works, how politics works. But being inexperienced is a problem you can solve, it’s something that you can fix through the people that you surround yourself with. Being cowardly, or politically timid, or unimaginative isn’t.” 

Aren’t too many of her proposed policies too radical for America? “Not at all. Not even a little bit. Everything that I’m proposing - from taxes, to infrastructure, to healthcare, to immigration - has already been implemented in many, many other nations. Frequently, they have been implemented in the past in this nation. But because we’ve been trapped for decades in a bully’s rhetorical paradigm, any practice that is actually liberal gets called radical, instead of being argued on its merits. Not on my watch.” 

I’ve been biting my tongue on one particular topic. Back in June of last year, I wrote the first big magazine profile of Amy Stirling, also known as the Silver Witch. If there’s anyone that has had an even busier year than Andrea Shepherd, it’s Stirling, who has only taken time off from a hectic period of touring to very publicly support Shepherd’s campaign for president. It’s an association that has raised some eyebrows, but its origins seem to truly be the stuff of innocent happenstance. Shepherd met Stirling when the former was a recent graduate from the political science major at Georgetown and the latter was still in high school. It happened when Shepherd took an internship with Alexandra Stirling, the fierce democratic strategist and campaign manager who masterminded over a dozen long shot victories in the Northeast. Would we call the fact that the two of them are now together in the fight for the nation’s political soul simply a bit of providence?

Shepherd wouldn’t say so. “It’s what happens in the wake of someone like Alexandra Stirling. She was, in so many ways, exactly who I wanted to be when I grew up: a smart, badass, well-read, capable, take-no-prisoners woman who fought like hell to make the country around her everything it should be - while also raising a daughter to be exactly as badass and awesome as she is, by the way. Half of what’s rolling around in here -” she points towards her forehead “- is because she put it in there. Not necessarily the ideas or the policies, but the approach, the attitude. She’s a huge figure in my life, a huge role model. It’s no surprise that Amy and I would become friends, or that we’d fight tooth and nail for the same vision of what our country should be.” 

Still, Ms. Stirling has been criticized for acting as a surrogate for the Shepherd campaign. Many, particularly those that support President Walker, have said that someone like her has no business in partisan politics, and back in the summer Ohio Congressman Hunter Kane suggested that both parties sign a pledge refusing any support from individuals like Ms. Stirling or Dr. Adam Blackwell. Congresswoman Shepherd declined. “End of the day, Amy is perfectly at liberty to voice her support for whoever she wants and to articulate why she supports them, the way any public figure, entertainer, or private citizen can. She is free to say whatever she wants and people are free to listen to her or not.” 

Having some previous experience with Ms. Stirling, I find myself having to push back against the Congresswoman. Because… that is not strictly speaking true. Ms. Stirling is quite literally capable of forcing someone to hear what she has to say, in a manner of speaking. Many are worried that she will use these talents to tip the scales in this election, perhaps in ways that would be virtually undetectable. Is her participation in these proceedings ethical?

“The idea that Amy would ever do something like that is both preposterous and repulsive, as anyone that has spent all of three minutes around her would know. That should really be the end of it, it’s as simple as that. But for anyone who needs a bit of reassurance? Amy cannot influence people long-term, she cannot influence them from afar, she cannot do anything en masse. Any scenario of her puppeteering people en masse on Election Day is just a paranoid conspiracy theory.”

It’s worth noting that Congresswoman Shepherd’s descriptions of Miss Stirling’s ability line up with everything that has been documented of her powers, as well as this writer’s personal experiences around the Silver Witch. Foreign thoughts, especially outlandish or unusual ones, are fairly easy to detect, and don’t persist when you’re no longer in her presence. “Simply put?” Shepherd finishes. “In terms of efficient ways to steal the White House, it’s a lot more practical and effective to go around the country, eloquently giving my arguments and persuading people to vote for me.” 

By this point, the crowd has finished streaming into the stadium, and the dull roar of thousands of avid fans yelling, “Bring it on!” the Shepherd campaign’s unofficial motto, is starting to make the walls vibrate. I only have time for one more question. 

Back in July of this year, a few weeks before the convention where she was acclaimed the Democratic candidate, Andrea Shepherd committed what many consider the worst faux pas of her campaign so far. In a TV interview with WNC, the candidate was asked what one thing she wished all American politicians would stop doing. Her answer - “Stop calling America the greatest nation on Earth” - has largely been seen as an unforced error. Now staring down the final stretch of the campaign, does she want to walk that back at all? 

“No,” Shepherd says, “I don’t. I believe America can be the world’s greatest nation. I believe it’s often been the world’s greatest nation. But I think that what makes us great isn’t our people, or our Constitution, or our resources. It’s the fact that American greatness is something we strive for, it’s an ongoing project that’s never finished. And the moment we start to treat greatness as something that we’re entitled to, something that’s our birthright, we stop earning that greatness. And I don’t want us to get complacent, I want us to earn it. I want us to work it.” 

“Because America is bigger than all of us. Everything we’re doing right now? It’s not about us. Not really. It’s about this great work-in-progress nation that’s going to outlive us all.” 

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