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How I Wound Up Chauffeuring a Mayoral Hopeful for a Day

Our correspondent shadowed Amara Enyia’s campaign for 48 hours — a very eventful 48 hours, it turned out.

Welcome to the first in a series of stories in which Barthwell, a pop culture writer and Second City improv instructor, embeds with top candidates in what promises to be the most wide-open mayoral race in this city’s modern history.

My first day shadowing the mayoral campaign of Amara Enyia began with drama. I made my way to Bucktown to attend a meeting with a taxi drivers’ organization and called Enyia’s communications director to confirm the address. My call was immediately sent to voicemail, and I received a text message from her shortly after saying that she was no longer Enyia’s communications director. Immediately following that, I, along with the campaign’s entire press list, received another e-mail from her saying her departure came after she received “troubling news.”

In the House of Cards or even Veep version of the two days I spent shadowing a Chicago mayoral candidate, the sudden and very public resignation of a communications director would be a development that would swallow the entire endeavor. A full episode would be devoted to the fallout and search for a new communications director. There might even be a hilarious montage of unqualified candidates. But for Amara Enyia, there was no need for handwringing; she just made a few phone calls while I, thrust into the role of driver in the wake of the resignation, shuttled her from event to event. Her interim communications director was literally appointed while she was stuck in traffic in the front seat of my car, a 2014 Ford Focus that I’d named after The Collector from the Marvel movies.

The emails from Enyia’s former communications director certainly made it seem like something was terribly wrong. But as I listened in on conversations among Enyia’s staff and to the statements the candidate composed on the fly, it was clear that this was a campaign gaining momentum due to self-assured appearances by Enyia and, in no small part, a few key celebrity endorsements (Chance the Rapper? Kanye West? EVER HEARD OF THEM?).

New staff was going to be coming on, including a new communications director with more experience in politics. The former one could expect a title change that she interpreted as a demotion. Perhaps she could have accepted the status shift or just left quietly. But she. did. not. choose those options. The news quickly spread to Twitter, and Enyia, 35, was quickly left fielding questions from the press and instructing her staff to update her website. Watching her work, it’s easy to feel impressed, even a little intimidated, by Amara Enyia. Not in that way that most white men mean “impressed” when they talk about meeting an intelligent and thoughtful woman of color. I just mean she’s really damn impressive. Standing next to her at events, I regretted my outfit choice of a striped turtleneck and black overalls. I looked like a mime on “Take Your Mime to Work Day.” She’s who you picture when you hear the phrase “She has it all.”

Enyia casually dropped that she has a PhD, but she’s a cool academic. You don’t have to call her “Dr. Enyia,” but she might ask you to, if she senses you’re trying to pull a fast one. She also has a master’s and a law degree — facts, again, that are just part of a conversation about how women’s expertise gets questioned. In an early e-mail with the campaign, Enyia offered that she usually goes for a run at 4 a.m. and is in the office shortly after, so I could just join her then. (I got exhausted just reading the e-mail. I decided to meet her later in the day). She’s done Ironman competitions, and she goes on a 100-mile bike ride once a week in the summer just to clear her head. I clear my head by knitting and recreating Milk Bar desserts from scratch.

The two days I spent with her campaign were a mix of public-facing events and closed-door meetings. We zig zagged around the city, and I personally paid for parking at no fewer than four garages. The first meeting, with a coalition from the United Taxidrivers Community Council, was at its headquarters, which are in the offices of In These Times, a nonprofit magazine focusing on economic justice issues.

Enyia had not arrived yet when I showed up, and my contact in setting all this up was suddenly no longer with the campaign, so my presence was a surprise to several people. I had to remind them, including members of Enyia’s staff that, yes, I was supposed to be there. I also had to inform certain staff members that I was not in college, and I couldn’t keep the snark out of my voice when I answered, “No.” You could hear the italics. On the eve of my 30th birthday, I don’t know that being confused for a college student is really a compliment anymore. What I’m saying is I had to make a few harried phone calls behind large potted plants to make sure I was in the right place.

The meeting with the taxi drivers started right when Enyia arrived at 1 p.m. Three guys named Rocky, Fez, and Frank led the discussion. They had helped coalesce the UTCC from disparate groups representing drivers across the Chicago area. They purchased a dozen Dunkin donuts and a jug of coffee. No one touched the donuts, but at one point, the CEO of UTCC instructed another member to pour a cup for “Miss Amara.” The UTCC wants to meet with all the candidates to introduce them to the issues facing its members here. One of the guys described the organization like “a United Nations on wheels,” with drivers originating from more 100 countries and speaking over 80 languages. They also not-so-subtly pointed out that they represent 2,000 to 3,000 votes in the city.

Enyia, who has cabbies in her own family, meets with the United Taxidrivers Community Council.

So what did the UTCC see as their biggest obstacle in achieving their goals of parity and fairness? The two greatest threats Chicago has dealt with in a generation: Rahm Emanuel and Uber.

It came up several times in the meeting that Emanuel’s brother Ari is a major investor in Uber and therefore his big bro Rahm will never be as tough on Uber as a mayor should be. One of the group’s more notable concerns was that the upper level at O’Hare was not built to sustain the increase in traffic due to rideshare pick-ups and could one day collapse. I had no idea that this was a concern for the city of Chicago, but now that it’s out there, I imagine that this will be the plot of Dwayne Johnson’s next blockbuster, AIRPORT CRASH.

After the meeting, UTCC wanted to give Amara a tour of their cozy offices with a memorial board of dead taxi drivers and maps of the city. The group’s PR person, who appeared to be an actual 20-year-old, wanted the photographer sent by Chicago magazine to take a photo of Enyia with the UTCC team. Since this brought up issues of copyright, a series of cell phone photos would have to do instead. Rocky, Frank, and Fez chastised their PR person about accidentally putting a finger over the lens.

After the photographs, the UTCC wanted Enyia to hang out at their offices a little longer. They wanted to talk to her about her family that immigrated from Nigeria; a few of her family members were taxi drivers. They called her “Miss Mayor.” They gave her a hug, adding “if that’s still allowed.” It was one of those jokes that doesn’t really feel like a joke.

Touring United Taxidrivers Community Council’s office.

Our next stop was a meeting with the Chicago Coalition for the Homeless in a high-rise office in the Loop, and that group had a PowerPoint prepared. They were meeting with as many of the 16 candidates as they could, to introduce them to policies they are pushing. They seemed thrilled to have Enyia in the office. A woman from coalition skipped over three bullet points on their agenda just to ask Enyia a question. The group is proposing a tax on real estate sales or developments over $1 million to use toward combatting homelessness. One of the most humbling things about this campaign-embed experience, other than reconciling with the fact that there are people in the world who begin their day at 4 a.m. while I struggle to get up before 11, was how little I know about how things get done in the city of Chicago. Listening to these presentations reminded me that I should, you know, read the local news or research what’s on my ballot.

At her meeting with homeless coalition, Enyia was joined by Kanu Iheukumere, her policy director. He knew her schedule, her policy positions, and was quick to make her and her team laugh. A woman at one of our campaign stops batted her eyes at Iheukumere, and he later had a room full of Enyia’s staff laughing at his reenactment of this woman’s sudden interest in public policy. His other job: He was often the first person to remind Enyia it was time to move on to the next event.

What would happen if someone didn’t remind Enyia of this? She would stay after every campaign event and answer every question, take every selfie requested, and explain and re-explain her positions. For someone like me who schedules when I’m going to leave a cocktail party, a candidate with the desire and ability to look at a room of people and not feel satisfied until every person has been heard seems admirable.

Alright, here’s where the whole thing got a little bit Goodfellas. After the meeting with Chicago Coalition for the Homeless, there was some downtime before Enyia was meeting with a private donor. She and I chatted in a nearby coffee shop in the lobby of a downtown building while Iheukumere answered e-mails and the photographer went in search of a snack. We found we had a few things in common. Neither of us were coffee drinkers. We both did speech and debate in high school; she did impromptu speaking and I did humorous interpretation. She had cousins who went to my high school, and she spent time in my hometown. Then she got a call that it was time to meet the private donor.

We walked down the street to meet with David Anderson, a former White House staffer who collaborates with businesses in African and other emerging markets as an executive at aviation services provider AAR. He added me on LinkedIn after we met, so I guess I’m someone who networks now. Anderson told the same story twice of a friend of a friend who manages the rapper Lil Pump, with the same punchline each time about Lil Pump trying to travel with weed in his pockets. We all walked a few blocks to go to one of Anderson’s favorite spots for dinner. We entered through a jewelry store on Wabash. I could see the tracking shot in my mind. Anderson knew everyone in the store and in the back was a Middle Eastern food stand. It wasn’t as glamorous as walking into the Copa Cabana through the kitchen, but it was a pleasant surprise after ping-ponging around the city and sitting in meetings all day.

Anderson bought everyone dinner, and Enyia told me they needed to have a private conversation. So the two of them sat a couple tables away and left me with their coats. There was a distinct “kid’s table” vibe. I maneuvered myself closer to their table by pretending to need to be near the water dispenser and listened in. Enyia was recounting the communications director situation from earlier in the day and asked for Anderson’s thoughts about staffing campaigns. The conversation was full of laughter, and if you didn’t look too closely, it could be mistaken for someone trying to impress his co-worker with his authentic dinner picks after work, not a meeting between a mayoral candidate and a fundraiser.

As they got up from their meal, Anderson asked me what I did and how I got involved with Chicago magazine. I briefly talked them through my writing career and mentioned Wakandacon, a Black Panther-inspired fan convention I organized this summer. Enyia’s face lit up. She spoke at Wakandacon. She was featured on a panel about the original Black Panthers of 1968 and the main character and film’s connection to the resistance group. Anderson offered to connect me with Michelle Obama’s former party planner, and Enyia had to meet her Lyft. My first embed day was done.

Enyia has dinner with David Anderson, a former White House staffer who now collaborates with African businesses, at Oasis Grill, a Middle Eastern restaurant in the back of a Wabash Avenue jewelery store.

The next afternoon, I joined Enyia at a podcast interview at the Harold Washington Library Center. The show, Scapi Radio, is hosted by two opera singers and highlights resistance art and community organizers. Picture two early 30s part-time opera divas slash podcast hosts. You are correct. In my notes I wrote, “Just two white people in scarves.” Their podcast has a respectable 3,000 followers on Facebook, and they acknowledged that those followers tend to be centered on the North Side, which means they tend to be white. Normally the two record their podcast in their apartment (they are a couple) with their cats but they moved to the library this time to accommodate Enyia’s packed schedule. It’s is an opportunity for Enyia to share her story: the daughter of Nigerian immigrants who now lives on the West Side, where she learned that residents there tend to live 15 to 20 years shorter than other areas of the city. The self-described “grassroots-organizer-slash-policy-wonk-slash-data-analyst” decided that the best way to help Chicago’s citizens is to ask them what they need. Thus her run for mayor in 2015 and again this time.

She prefers long-form interviews, she says, because it allows her a more comprehensive explanation of her policies. This podcast focused on her cooperative economy proposals — workers owning means of production, establishing a land trust with shared citizen ownership, and other words that confused my brain but delighted the hosts’ socialist leanings. During a discussion about a proposed Target leaving the South Side, Enyia calmly lays out how and why a business decision like that can diminish the area. She makes the argument that marginalized people in the city don’t have the opportunity or the means to say, “Screw you, we’ll build our own.”

She describes her 2015 campaign like Lord of the Rings, a bunch of scrappy misfits marching toward a seemingly impossible goal. Her staff is more organized now and have a clear vision of what victory looks like. Four years ago, the ideas she was talking about and proposing were ahead of their time. Ideas like creating more employee-owned businesses and fairly distributing tax revenue from programs like TIFF in blighted areas. Now, in 2018, when people are looking to create new economic systems that work for people, her anti-establishment ideas are more accepted.

After changing into her comfy winter boots, Enyia catches a ride with me again to an endorsement interview with the Chicago Federation of Labor, where she’ll be joined by other candidates. In the car, Enyia gets notice that the Tribune is requesting mayoral candidates’ tax returns. (She has refused to release hers.) This is the first time I’ve seen her get heated. She explains: For a candidate coming from a grassroots-organizing background, a modest salary is seen as a knock against them because merit is often tied to wealth. I bring up Stacey Abrams’ student loans being a liability in her losing the gubernatorial race in Georgia. Enyia’s take is, with an ask like this we are judging candidate on some impossible-to-nail-down standard. It’s a purity test, but we’re not exactly sure what purity looks like.

The Chicago Federation of Labor meeting turns out to be closed to anyone other than the candidates. I’m stuck in the lobby with all the campaign managers, aides, and security. Someone appears from the breakroom and offers us party trays of pasta and salad, and I get to hear campaign staffers share war stories. There’s talk that Toni Preckwinkle and Bill Daley got to do the interview alone and not fight for time with the other candidates. Each had their campaign director in with him so this whole thing might be rigged, according to one campaign manager in the lobby. Two staffers argue that an endorsement this early is essentially useless unless it comes with money. Another keeps repeating that the race will probably end up with about 10 to 12 candidates, and anyone can win. The way she keeps repeating it feels like a statement of hope and despair.

The phrase “well, everyone knows…” starts every opinion from every staffer. Everyone knows certain candidates can’t fulfill their promises and are just doing it for exposure. Everyone knows that ballot petitions always get challenged so throwing a fit about it is a waste of energy. Everyone already seems tired, everyone knows everyone. As I’m on my way out to retrieve my car, I hear a male campaign manager say, “I have four former clients in this race.”

The final stop for the Enyia campaign is the Disability Forum hosted by Access Living of Metro Chicago in River North. When I arrive, I’m ushered into an office that’s been converted into a green room with a few members of Enyia’s staff. Most of them assume that I’m a new team member. The forum, full of mayoral candidates, feels like something out of Parks and Recreation. There’s La Shawn Ford, a state representative who starts every answer with “as a teacher.” There’s John Kozlar, who starts every answer by reminding us that his 30th birthday is tomorrow and has the energy of a sentient Bears jersey. Susana Mendoza keeps repeating a story about a citizen who wrote her a letter on her first day as comptroller.

Before the forum begins, Iheukumere shares a video with Enyia’s staff from Rickey Hendon, a political consultant for Willie Wilson. Streaming live on Facebook, he had recounted a heated situation at the country board of elections as candidates were turning in their signatures to get on the ballot. According to Hendon, Ja’mal Green believed the Wilson team were unnecessarily challenging his signatures and started to scream at Hendon, basically calling Willie Wilson a scammer. This is definitely a rejected storyline from a season of Real Housewives of Atlanta. Everyone in the room seems willing to laugh at the video at the first viewing, but when I ask for clarifying information, no one seems to be willing to offer any. In their mind, it’s just a funny video, not a piece of important political insight.

That’s not the only piece of drama at the forum. The candidates were split into two sessions, and apparently when Toni Preckwinkle arrived, she double-parked a county vehicle in front of the building, blocking the unloading zone in front for the entire duration of the first session. It goes without saying: the balls it takes to illegally park outside a center dedicated to finding accessible housing for people with disabilities during a forum about issues of disability. An Enyia staffer wanted someone to take a photo of Preckwinkle’s car in the loading zone. The general tone among the campaign staffers: Preckwinkle is a front runner and she knows it, so she thinks she can do whatever she wants. Everyone seems content to try to snap a photo of her error.

After 48 hours with the Enyia’s campaign, I learned a few things. I learned that Enyia, who has worked in the mayor’s office and is a member of the Austin Chamber of Commerce, seemed to know by name every alderman and county board member we ran into. She seems adept at gauging how her policy will be received in various meetings and adjusting on the fly. Her solutions always felt holistic and considered how various systems interact with the lives of Chicago’s citizens.

I also learned I do not have what it takes to run for office. Especially not in Chicago. It’s too easy to get caught up in the drama and gossip that surrounds politics. Everything outside of the events themselves felt like an exercise in patience and restraint. It was a lot like a competition on reality television: You might go into the whole experience convinced that outsmarting the competition itself or hoodwinking your competitors is the way to succeed, but the people who emerge as standard bearers are the ones who put their head down, work hard, and never snatch their own wig off.

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