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The Worst Wing

How the East Wing shrank Michelle Obama

SAUL LOEB/AFP/Getty Images

In the fall of 2010, the nasty midterms drawing to a close, Michelle Obama was contemplating her next move. Two years into her tenure as first lady, the breathless fixation on guest lists and china selections was subsiding into routine, and she wanted a plan for the rest of her husband’s time in office. Of course, her calendar would never lack for National Hostess duties—the obligatory social functions outlined in binders left by Laura Bush’s team. She had already launched Let’s Move!, the childhood obesity initiative, and Joining Forces, a program to help military families and veterans, was also in the works. But she wondered whether she should do more. And so the first lady directed her staff to conduct a review of her options and to hire a top-flight communications director to lead the effort. Some palace watchers had been underwhelmed so far by her agenda, and this was an opportunity to prove these critics wrong.

Perhaps no first lady in recent memory has entered the stately recesses of the East Wing under a higher burden of expectation than Michelle Obama. From her earliest appearances on the 2008 campaign trail, it was clear that she possessed rare political gifts. Like Hillary Clinton before her, she was an accomplished lawyer with policy smarts. But unlike Clinton, she was also an electrifying speaker, able to translate her husband’s lofty agenda into a grounded, commonsense morality. When Michelle Obama entered the White House in 2009, she attracted staffers eager to bring about the policy prescriptions that she had so forcefully advocated on the trail.

This meant that, when it came to the search for a communications director, the office had no trouble finding a candidate with impressive credentials. Kristina Schake, a California political operative, had led the fight against California’s Proposition 8 and helped steer Maria Shriver’s annual women’s conference, widely hailed as a breakout success. Schake’s hiring seemed to signal that the first lady was ready to embark on a new phase, focused on issues of public health and equality. “Reading the tea leaves, I was struck by the level of ambition it communicated,” says Jodi Kantor, the New York Times political reporter and author of a book about the Obamas.

Two and a half years later, Schake would be out the door, replaced by an executive from Estée Lauder. What Schake couldn’t have known in 2010—and what Mrs. Obama’s hyper-motivated, highly accomplished staffers would never publicly admit—is that the first lady’s office can be a confining, frustrating, even miserable place to work. Jealousy and discontentment have festered, as courtiers squabble over the allocation of responsibility and access to Mrs. Obama, both of which can be aggravatingly scarce. Fueling these sentiments, according to former East Wing insiders, is the exacting but often ambivalent leadership style of the first lady herself.

Illustration by Michael Marsicano

The First Lady’s offices run along a hushed corridor on the second floor of the East Wing, where the policy team occupies an office next to the calligraphers who write ornate invitations to the mansion’s many formal events. That the position of first lady has become embarrassingly anachronistic is no big revelation. But after the 2008 victory, there were hopes that Michelle Obama’s political appeal and charisma would enable her to transform it into something that reflected the role of modern women as equal participants in the political process.

Surprisingly, though, her first move was to declare that she wanted to play it safe. A few days before her husband took the oath of office, she gathered her small staff at the presidential transition headquarters in downtown Washington and outlined a distinctly narrow vision. “We don’t have to do anything,” she told her aides, according to people familiar with the meeting, “so anything we decide to do, we need to do really, really well.” She didn’t want to get in the way of the president’s agenda, she explained. She only wanted to be, as she would say often over the years, “value-added.”

At the time, this was interpreted as a justified caution, borne of her unpleasant experiences on the campaign trail. Michelle Obama had been at the height of her galvanizing, truth-telling power when, in February 2008, she declared in Madison, Wisconsin: “For the first time in my adult lifetime, I’m really proud of my country. And not just because Barack has done well, but because I think people are hungry for change.” The backlash was predictable and swift, and her husband’s advisers quickly steered her away from the rhetorical barbecue and toward the saltines. “She’s your ultimate straight-A student; she was used to being perfect,” one former aide told me. “That was a defining moment for her.”

In truth, though, Michelle Obama has always been cautious, especially when it comes to her family’s public life. Before Barack entered the presidential race, she held a series of meetings with David Axelrod to rigorously assess everything from her husband’s chances of actually winning to where the girls would go to school, according to the biographer Liza Mundy. Unlike her husband, who derives visible satisfaction from his ability to improvise, Mrs. Obama depends on structure to support her public warmth—the ease with which she’ll pick up a hula-hoop, say, or do the Dougie with school kids.

That mandate to be deliberate in all things has been enshrined into East Wing operating procedure. In that early meeting and in the months following, Mrs. Obama made it clear to her staff that—endless compulsory East Room receptions aside—her time was a valuable asset and requests to use it would have to meet an exceptionally high bar. Every event should focus on a concrete, achievable goal, like announcing a new corporate partnership. She would only be available for official duties two or three days a week; the remainder would be devoted to family responsibilities. One ex-employee observed, diplomatically, “It would take a really creative staffer to work within that environment and be successful.”

For one thing, the imperative to guarantee results could be paralyzing. “That was the pressure on us,” one ex-aide told me. “‘Don’t do it if it’s not going to be perfect.’” Staff knew that every event should produce positive coverage, and that all the angles had to be exhaustively researched and gamed out (not easy with a team of less than 30). But it was never completely clear what the standard of perfection should be. “There’s no barometer: The first lady having the wrong pencil skirt on Monday is just as big of a fuck-up as someone speaking on the record when they didn’t mean to or a policy initiative that completely failed,” says another former aide. “It just made you super anxious.” Another past employee described a common feeling of “how can we be the caliber that we’re expected to be with no attention and no resources and being an afterthought? And all that can make for sparks. Friction.”

Former staffers describe a high-stress, high-stakes workplace, in which Mrs. Obama scrutinized the smallest facets of her schedule. Aides in both wings of the White House say she insists on planning every move months in advance and finalizing speeches weeks ahead of time—a rigidity nearly unheard of in today’s chaotic political environment. “For her, trust is huge, really feeling like people were protecting and thinking about her,” says one alum. “And then, also, she’s a lawyer. She’s really disciplined. She cares about the details. She’s never going to wing it.” The alum explained that staffers would often want to run an idea by Mrs. Obama casually, to get her read on it. “That kind of doesn’t work for her,” the alum said. “You have to fully think it through and be ready for questions.” It didn’t help that the West Wing, which was often absent during the long pre-planning phase, could swoop in on the day of an event to gripe about its execution. (I worked in the White House press operation until March of 2011, but rarely worked closely with the East Wing.)

All of this led to a culture of harsh internal judgment. Invitations to meetings with the first lady, in her office above the Jackie Kennedy Garden, became a vital status symbol, a way for staffers to measure their worth. “Every meeting was like an identity crisis, whether you got invited or not,” one former East Winger told me. Casual face-time with Mrs. Obama was coveted as a badge of insiderdom. “Everyone sort of stands at attention in a different way, or they try to make the joke, or they try to be the one noticed, or they try to get the smile,” says a former employee. “And that’s in part a yearning for acknowledgment that you’re part of this, something bigger, and that she knows who you are.” Another former employee put it more bluntly: “They don’t want to work for her; they want to be friends with her.”

Few have succeeded. Mrs. Obama has consistently shown a strong preference to be surrounded by aides with whom she has long-standing ties. “She’s the kind of person who, if you know her a long time, you get to the point with her where you’re loved,” says a former White House staffer, “but it’s really hard at first.” Within months of taking office, Mrs. Obama replaced her first chief-of-staff, Jackie Norris—who had overseen the campaign’s stellar Iowa operation—with an old friend, Susan Sher. When Sher returned to Chicago at the end of 2010, Tina Tchen, another Chicago lawyer who’d been working in the White House Office of Public Engagement, settled into the chief-of-staff job. Former employees say that Sher and Tchen both emphasized competence and conflict-avoidance over grand vision. Most important, both were comfortable taking orders from Valerie Jarrett, the first lady’s self-appointed enforcer and avatar. Let’s Move! saw its first two directors wash out—one a veteran political organizer and the next a pediatrician—to be replaced in 2013 by Sam Kass, the Obamas’ longtime chef and garden-master.

Kristina Schake, consigned to this environment, did her best. She pushed to broaden Mrs. Obama’s audience without exceeding her boss’s willingness to take risks. It was Schake who recommended that the first lady appear with celebrities like Jimmy Fallon for what have become familiar bouts of silliness: feeding kale chips to Fallon and Will Ferrell, or dunking a mini basketball on LeBron James as Dwyane Wade reads healthy-eating tips. Those appearances won important attention for the first lady’s signature issues.

They also won Schake admirers in the West Wing, where the president’s advisers had long been suspicious of the seriousness of Mrs. Obama’s operation. Jennifer Palmieri, now the communications director in the West Wing, quietly approached Schake about taking the deputy job there, a de facto promotion. At the same time, Schake was talking to the East Wing about taking on an elevated role. When word got out about the West Wing job, the process blew up—apparently over whether Schake had the first lady’s permission to pursue the job with Palmieri. In the private sector, a talented candidate will pursue any and all opportunities for advancement, but in the East Wing it was a violation of trust, Mrs. Obama’s core principle. Schake (who declined to comment) left in June 2013 for a job at L’Oreal.

Her strategic review, though, had at least one lasting impact: the addition of an initiative on education equality to the first lady’s agenda. The goal is to encourage more young people, especially those from underserved populations, to achieve a college education. It’s a cause that Mrs. Obama is clearly passionate about and one that harnesses the power of her own life story. And yet insiders say that the program has so far fallen short of one of the strategic plan’s key recommendations—that it be supported with substance, like proposals for legislation or policy changes among higher-ed institutions. “Maybe they’re easing their way into it,” one former staffer told me hopefully.

In September, the first lady jetted to Watertown, Wisconsin, for a new initiative named Drink Up. The idea was to try to counter the marketing oomph of the makers of sugary drinks. Joined by Eva Longoria, Mrs. Obama led Watertown’s high school students in a toast with Drink Up–branded water bottles and participated in “water games.” The kickoff did not go entirely smoothly. Nutrition activists questioned why Big Soda companies were among the program’s corporate promoters. Watertown had presumably been selected because of its name, but a local paper noted that one of the town’s major employers is a soda-bottling plant. (Vetting can be a casualty of the East Wing’s under-staffing.) The whole thing felt a bit like an episode of “Veep.”

Michelle Obama will be first lady for three more years, and the status quo is likely to continue. The office ranks have filled out with operatives comfortable with Watertown-style initiatives, and several say this has led to a less fraught workplace environment. Chief among the decision-makers are Kass and Jarrett—old family friends who enjoy rare access to the president and first lady’s ultra-secluded living quarters, and to Mrs. Obama’s private thinking. (Drink Up was a Kass brainchild.) The first lady remains broadly popular, and her office has contributed to some laudable gains: “From day one, the First Lady ambitiously set out to make a measurable impact on the lives of everyday American families,” reads a statement provided by the East Wing to The New Republic. “From a recent CDC report that found that the obesity rate for young children plummeted 43 percent in the last decade to 380,000 vets hired since the inception of Joining Forces, the First Lady is laser-focused on moving the needle wherever and whenever possible.”

And yet it’s hard not to harken back to the Michelle Obama of the early 2008 campaign. Just a few days before her speech in Madison, Mrs. Obama headlined a rally in the old music hall in downtown Cincinnati. As an itinerant campaign staffer assigned to the event, I watched from the back of the hall and was struck by the palpable force of her argument. She talked for an hour about race and inequality in frank, critical terms. At one point, she told a story about a young African American girl who had approached her at an event and told her that, if Barack Obama won the election, it would mean that she could be whatever she wanted when she grew up. Then the girl had burst into tears, Michelle told the crowd, because she knew that her country was already leaving her behind. There was no one else on the national scene who could tell a story like that and have it mean so much. I went back and searched for coverage of the rally but found only one brief clip on YouTube. There was a short story in The Cincinnati Enquirer, but it is locked away in the paper’s archive. Otherwise there is nothing, as though the event never happened.

Reid Cherlin, a former White House assistant press secretary, is a writer living in Brooklyn.