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  1. Photograph: Elizabeth Jochum
    Photograph: Elizabeth Jochum

    Emanuel's young staffers: Mike Simmons, from left, Ankur Thakkar, Caroline Weisser, Matt Fischler, Anna Valencia and Michael Faulman

  2. Photograph: Tim Klein
    Photograph: Tim Klein

    Ankur Thakkar and Caroline Weisser talk in the press room at the mayor's office.

  3. Photograph: Tim Klein
    Photograph: Tim Klein

    Ankur Thakkar and Caroline Weisser talk in the press room at the mayor's office.

  4. Photograph: Tim Klein
    Photograph: Tim Klein

    Ankur Thakkar (from left), Anna Valencia and Caroline Weisser in the mayor's office

  5. Photograph: Tim Klein
    Photograph: Tim Klein

    Staffers from the mayor's office exit through the front door.

  6. Photograph: Tim Klein
    Photograph: Tim Klein

    Caroline Weisser (from left), Matt Fischler, Anna Valencia and Ankur Thakkar walk through Daley Plaza.

  7. Photograph: Tim Klein
    Photograph: Tim Klein

    Matt Fischler (left) and Mike Simmons discuss city policies in Simmons's office in City Hall.

  8. Photograph: Tim Klein
    Photograph: Tim Klein

    Michael Faulman (from left), Anna Valencia and Mike Simmons

  9. Photograph: Tim Klein
    Photograph: Tim Klein

    Caroline Weisser (from left), Matt Fischler, Anna Valencia and Ankur Thakkar on a coffee break

  10. Photograph: Tim Klein
    Photograph: Tim Klein

    Matt Fischler at an informal meeting with one of his colleagues at City Hall.

  11. Photograph: Tim Klein
    Photograph: Tim Klein

    Mike Simmons (left) with Michael Faulman at City Hall

  12. Photograph: Tim Klein
    Photograph: Tim Klein

    Mike Simmons (left) and Michael Faulman at City Hall

  13. Photograph: Tim Klein
    Photograph: Tim Klein

    Mike Simmons (from left), Caroline Weisser, Matt Fischler and Michael Faulman

  14. Photograph: Tim Klein
    Photograph: Tim Klein

    A portrait of Mayor Rahm Emanuel hangs in a hallway at City Hall.

  15. Photograph: Brooke Collins
    Photograph: Brooke Collins

    Ankur Thakkar (left) and Matt Fischler lend support while the mayor makes a major announcement about introducing Chicago's new Welcoming City Ordinance.

  16. Photograph: Brooke Collins
    Photograph: Brooke Collins

    Ankur Thakkar checks the Twitter chatter as the mayor announces the upcoming introduction of the Welcoming City Ordinance.

  17. Photograph: Brooke Collins
    Photograph: Brooke Collins

    Matt Fischler and Ankur Thakkar provide feedback to Chicago Office of New Americans Director Adolfo Hernandez post-event, where the mayor announced the new Welcoming Chicago Ordinance.

  18. Photograph: Brooke Collins
    Photograph: Brooke Collins

    Anna Valencia waits while the mayor discusses an upcoming announcement on immigration with Chicago aldermen and U.S. Rep. Luis Gutierrez.

  19. Photograph: Brooke Collins
    Photograph: Brooke Collins

    Caroline Weisser works behind the scenes during a press announcement aimed at investing in infrastructure and rennovating CTA facilities.

  20. Photograph: Tim Klein
    Photograph: Tim Klein

    Newspaper clipping of Rahm Emanuel hang on the wall in Caroline Weisser's office at City Hall.

What it’s like to work for Rahm Emanuel

Six twentysomethings tell their tales of tweeting for, traveling with and taking date-night suggestions from Mayor Rahm Emanuel.


ON THE FIFTH FLOOR OF MAYOR RAHM Emanuel’s City Hall offices, there’s a room with dozens of printed screenshots and handwritten notes taped to one wall. Above the papers in small black letters, a hand-drawn sign reads: awesome shit wall.

Caroline Weisser, an assistant press secretary for the mayor, is leading me on a tour, and we’ve stopped in the office of 28-year-old Kevin Hauswirth, the mayor’s director of social media. “Everything in this room is off the record,” Weisser, 25, declares, “except for this wall.”

This wall is where Hauswirth and Ankur Thakkar, the deputy director of social media, post their inspirations. Some of them are ideas they’d like to implement for the mayor’s office. Others they simply find humorous. Posts range from a screenshot of a Muppet Facebook app that allows users to record themselves singing a few seconds of the movie’s theme song to a screenshot of a video player with a sidebar of rolling commentary that would enhance a live address. Nowhere in the mayor’s office is youth culture more prominently on display than here.

Despite Emanuel’s reputation of not being an easy man to work for (a Time magazine article famously described him as a “profane, hyperactive attack dog” with a “steamrolling personality”), several twentysomethings dropped their lives in cities such as Washington, D.C., New York and Springfield, Illinois, when they got offers to work for Chicago’s first new mayor in 22 years.

Some, like Thakkar, are helping build a social-media presence for the mayor’s office. Others, like Weisser, are handling the press and working damage control. Then there’s 28-year-old mayoral aide Michael Faulman, who once found himself eating salami and hummus with Emanuel in a Jewel parking lot. Here, six millennials tell their stories of what it’s like to work for one of the nation’s most intimidating politicians.

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THAKKAR, 28, IS A PHILOSOPHICAL GUY sporting a beard and a stylish skinny tie. Along with Hauswirth, he is building the office’s Internet presence nearly from scratch. Because of Thakkar, you can see photos on Instagram of the mayor hanging backstage with Conan O’Brien or catch Emanuel checking in on foursquare at the Milwaukee Avenue Arts Festival. Thakkar live-tweets mayoral press events on an iPad and manages the mayor’s office’s Facebook, Twitter, Livestream, Google+, Storify, YouTube, foursquare and Instagram accounts. The accounts usually reference Emanuel in the third person; the @RahmEmanuel account, established during the campaign, is still used to promote the mayor’s activities. When Thakkar first met Emanuel about a month after he started his job, he wanted to blurt out, “I am you, on the Internet.” But he got scared, and instead he smiled.

Emanuel has been described as a fear-inspiring boss. “We joke that someone should open a special trauma ward…for people who’ve worked for Rahm,” a former staffer during Emanuel’s years as a senior advisor to President Clinton once told Rolling Stone.

But Emanuel’s twentysomething employees—who make up just over one-third of the mayor’s staff of 85—describe their boss as more like a tough but fair professor whose expectations they want to exceed. He challenges them to take decisive action, just as he does. He’s a role model who excelled at a young age, as they hope to.

Junior staffers speak fondly of the life lessons Emanuel has taught them: Pay attention to details, read as much as you can, don’t lose the human connection in the digital age. When his field director, Anna Valencia, got sick on the campaign trail and had to stay at Northwestern Memorial Hospital, Emanuel wanted to see her. “Please, no!” she had to plead with Faulman. (As Emanuel’s “body guy,” he travels everywhere with the mayor while Emanuel's on the clock.) “I was in a hospital gown dying,” Valencia, now 27, later joked.

Emanuel is demanding, aggressive and expects his staff to work long hours, his young aides admit. But many of them sought out this fast-paced environment, where they’ve been tasked with big responsibilities. Matt Fischler, a 24-year-old policy associate, helped launch the mayor’s Office of New Americans, the first citywide office that focuses on immigration. Mike Simmons, the mayor’s 29-year-old policy director, has been integral in implementing Emanuel’s strategy to eradicate Chicago food deserts.

“No one who values a comfortable, show-up-at-9:30-and-leave-at-5 [job] is going to want to work for Rahm Emanuel,” as one former employee put it. “It’s a staff of workaholics, let’s be honest.”

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IT’S THE DAY AFTER THE FOURTH OF JULY and I’m sitting in Valencia’s City Hall office. We’re joined by Faulman, Simmons and Weisser, whom I met about a year ago through my roommate.

Though Weisser is not being interviewed today, she stands in the corner typing on her BlackBerry, occasionally prompting the others to elaborate on or clarify what they’ve said. (The mayor’s office let five of its young staffers speak with me on the condition that Weisser sit in on my interviews, which is standard procedure there. I was allowed to interview her alone.) Fresh off a holiday, everyone is more relaxed than I’ve seen them over the last few weeks.

“The fourth floor is like the stepkids…people forget we’re down here,” Valencia says of her office, which is one floor below the mayor’s. Valencia works for the mayor’s legislative counsel and government affairs team, where she does everything from brief elected officials about upcoming press events to wrangle aldermen for photo ops. Her office is brightly lit and decorated with pink flowers from the Daley Plaza farmers’ market.

Towering at six feet tall with closely cropped blond hair, Faulman can barely fit his lanky frame in his chair. With no meetings scheduled today, he’s traded his usual suit and tie for a more casual green polo and brown boat shoes. Of all the twentysomethings, Faulman spends the most time with Emanuel—nearly every work day since October 2010. He jokes they’re “like a couple.” They shoveled cars out of the snow together during the February 2011 “Snowpocalypse.” Faulman has taken date-night restaurant suggestions from Emanuel, who is known as a foodie around the office. Once, on the campaign trail, Emanuel asked the car to pull over at a deli. “You’re German,” he said to Faulman. “I’m going to show you how Jewish people eat.” Then Emanuel placed his order in Hebrew: lox on a toasted bagel and challah-bread French toast.

But not many colleagues envy Faulman’s job. Valencia says she “had to be Faulman one night” and found it “nerve-racking” and “terrifying” to sit alone in the car with the mayor. As he describes it, Faulman is the mayor’s “eyes and ears,” helping keep Emanuel’s schedule running smoothly and anticipating anything he may need for a speech, meeting or press event. Faulman carries hand sanitizer, Listerine Strips and note cards in his pockets and the mayor’s briefing book in his hand at all times. He’s cool under pressure and has a penchant for deadpan sarcasm.

“[We] don’t talk shop all the time,” Faulman says of his time with Emanuel. Cracking jokes, he explains, helps alleviate stress.

Simmons, the most serious of the bunch, considers my questions carefully before answering. He came prepared for our first interview with a few pages of typed notes. He is the No. 2 to David Spielfogel, Emanuel’s chief of policy and strategic planning.

Simmons was among only two twentysomethings on Emanuel’s list of senior staffers released last May. But he escaped the scrutiny the mayor’s press secretary, Tarrah Cooper, faced. A few days after the staff announcement, Chuck Goudie, a reporter for ABC, wrote a Daily Herald column in which he questioned Cooper, then 25, and her qualifications “to be press secretary for the mayor of the third-largest city.” He asked her the loaded question: “Does your youthfulness and lack of experience symbolize what seems to be [an] administration focused on hiring managers under 35?” (The mayor’s office declined my request to interview Cooper.)

Weisser brushes off the column as the opinion of an older man. She and other young staffers are quick to dismiss their youth as a source of workplace problems. They are well-qualified for their jobs, they say, and besides that, politics and communications tend to be youth-staffed fields.

Simmons concedes age can be an obstacle, albeit a “surmountable” one. “It would be fair for me to admit as a young person I’m going to need to be three times as well-prepared, three times as poised, three times as informed,” he says. “That said, I think when I do show up to discuss important policy with…someone who’s been in public service for twice as long as I’ve been alive, if I know my stuff…I usually find that I’m taken pretty seriously.”

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SEVERAL OF EMANUEL’S YOUNGEST employees bonded on the campaign trail, when it was common for staffers to eat all three meals together as they shared an “all-consuming” schedule: seven days a week from early in the morning until 11pm. They also had time to bond during the mayor’s first, frenetic 100 days in office. They trust and rely on one another to get work done.

Many of the young staffers have similar personality traits: They’re geeky, sarcastic, modest and genuinely passionate about Chicago. They’re all trying to figure out how to balance their work ethic with a normal life. (A thirtysomething senior spokesperson for the mayor describes millennials in politics as having a “paranoia that I’ve got to work harder than anyone else because if I stop they’re going to take [my job] from me.”)

It’s not unusual to see the young staffers grabbing after-work drinks at Twisted Spoke, Big Star, the Red Canary, Nana or Monk’s Pub. They set one another up with friends: “I try to play the matchmaker with the outside world,” says Valencia, who is known around the office for throwing great parties. While leaving a recent Little Village press conference before the rest of his team, Fischler calls over his shoulder: “You’re going to bring me tacos!”

At Weisser’s 25th birthday party at Haymarket Pub & Brewery in late June, several of her colleagues are in attendance. Dressed in a snug pink scoop-neck dress, Weisser sways in the dim lighting to a mix of ’90s pop and Top 40 hits before leaving to meet up with another staffer at Bonny’s in Logan Square.

“I’m friendly and social with all my coworkers,” Weisser explains to me over gelato at Lavazza, a coffee shop near City Hall. “You can go out for drinks…after work and you can tell funny stories about when you were in college…and then go into a meeting” without worrying about anyone blabbing.

Emanuel is known for careful staging, and his press shop is the kind you’d expect from a Washington politician: revisionist, controlling and hyper-image-conscious. Staffers were hesitant to talk about their personal lives for this story. After Goudie’s column criticized Cooper’s public Facebook page that showed “her partying with friends, in beach attire and at a slot machine,” Cooper made her profile private. Other staffers also keep their photos private and the few you can see are usually of Chicago: the skyline, the flag.

During my reporting, Weisser, who is cheerful but has what a former colleague describes as a “no nonsense, no bullshit” approach to her work, serves as the office’s reputation monitor. For the most part, she does not interrupt my interviews, but she does follow up meticulously to request that I clean up language ( I decline).

As Valencia says of her own job: “It’s all about the mayor and making sure we’re moving his agenda forward and we have a good image for this office.”

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NONE OF THE STAFFERS I TALK TO HAVE concrete plans to run for office one day. Simmons says it’s difficult to map out your life plan when your current job is already time-consuming and professionally challenging. But young staffers knew the new administration would be addressing questions around job creation, infrastructure, long-term economic development and Chicago’s role as a global city, and they wanted to play a part in coming up with the answers.

“[Emanuel is] revolutionizing what mayors do,” Faulman says. “To be a part of that and to see the changes, both good and bad… I think we’re pretty lucky. We’re witnessing history.”

Fischler left New York Mayor Michael Bloomberg’s administration to work for Emanuel. He says when he was in middle school, he watched The West Wing with his mother and imagined he’d one day work in the White House. But after several internships he realized “the federal government is so monstrous, you can barely get anything done.”

“City governments are the laboratory for policy innovation,” Fischler says. “It’s been really cool to see ideas from conception all the way to implementation.”

Simmons worked on policy for Cook County commissioner Bridget Gainer before joining the mayor’s team. To accomplish good ideas, he says, you need the foresight to predict which policies are doable and how they will be received across the city.

To do that, Simmons taps into his humble upbringing in Lincoln Square, back when the neighborhood was working-class and ethnically diverse. Simmons’s parents—who met at the Wild Hare, a popular reggae bar in Wrigleyville that Simmons’s father later purchased, ran for 30 years and closed before returning to his native Ethiopia last year—were constituents and supporters of Emanuel during his six-year stint in Congress.

“I don’t come from a well-connected family at all,” Simmons says. “I didn’t grow up with any money. These are all things that I think give you an out-of-the-box understanding of…policy.”

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IT’S AN 80-DEGREE JULY NIGHT AND cicadas are buzzing in the trees. Weisser and I are standing in Union Park, watching the mayor’s office softball team, the Four Stars, warm up for a game against the governor’s team, the Quinners. Thakkar rides up to the field on his bike wearing the Four Stars’ jersey: their namesake four-starred Chicago flag on the front and a number five on the back, for the mayor’s floor in City Hall. After waiting in vain for more female players to arrive (they need at least two), the Four Stars have to forfeit and play for fun.

Thakkar takes the field with Derek Lindblom, chief of staff of the mayor’s economic council, and Jacob Ringer, chief of staff to the city’s chief financial officer. Thakkar misses a pop-up foul and laughs sheepishly. Lindblom grabs him on the shoulder to say it’s okay, before throwing a ball that flies high over Thakkar’s head at third base. “[That play] was really egregious,” Ringer teases Lindblom later.

The Four Stars are down by several runs. They get a few base hits, then Tom Alexander, assistant press secretary, hits a grand slam. In true mayoral fashion—an Emanuel mantra is “Don’t spike the ball on the 15-yard line”—the Four Stars keep up the pace, winning by four, even though the score doesn’t count. They smile briefly at one another, say their good-byes quickly and head home to rest up for another day at City Hall. It’s not so different from how Valencia describes wins in the mayor’s office: “Once we hit an accomplishment, get back to work because there’s more to get done.”

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