Checking in with the Chicago Contingent of the Obama White House

MIDWEST WING: Giordano’s pizza ordered from the White House? Goose Island beer at Washington parties? A crew of young Chicagoans has followed Obama to the capital. They are bringing a touch of home to D.C.’s social scene—just as Washington ways are shaping them

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Chicago’s winners and losers in Election 2008

The new Chicago crowd entered Washington with its own social structure. The senior staffers—Axelrod, Emanuel, Sher, Valerie Jarrett, and Desirée Rogers, to name a few—had crossed paths for decades back home and were close personal friends of the Obamas. The junior staffers had forged tight friendships during the long campaign as members of Obama’s grass-roots army.

“It wasn’t just that they’re from Chicago,” says Tammy Haddad, a longtime Washington producer who is now president of Haddad Media. “They lived in Chicago. That’s where the campaign was.

“They are kind, they are polite, but they are very disciplined, and they only say yes to what they want to say yes to,” she continues. “They have a defined sense of how they should do things, and I think it’s because this whole culture moved as a group.”

Many of the young Obama staffers live and play in an area they jokingly call “campus”—the up-and-coming U Street Corridor, a once-dilapidated strip that’s now dotted with hip restaurants, trendy wine bars, and basement jazz joints. The campus loosely stretches from Dupont and Logan circles up to Columbia Heights and Mount Pleasant. Some of the more senior staffers, such as Peter Cunningham, the assistant secretary for the Office of Communications and Outreach at the Department of Education, also prefer the more gritty feel of the area.

Until Desirée Rogers left her job in the White House social office, she lived in the same Georgetown waterfront apartment building as Jarrett and Sher. “I was literally sleeping on Valerie’s couch,” says Sher, recounting her first weeks in Washington. “Desirée stopped by Valerie’s apartment and said, ‘Hey, there’s an apartment across the hall that’s about to be up for rent,’ so we walked across the hall and looked at it, and I said, ‘OK, fine.’”

Midwesterners groan at the “Chicago mafia” moniker, but in many ways the teasing nickname also belies a subtle tension: the struggle between their tight existing circle and a city eager to check them out, draw them in, win them over, co-opt them a bit, and then, maybe, spit them out.

Quinn says she admires the effort led by the Obamas and Desirée Rogers to turn the White House into “the people’s house”—little touches like bringing in neighborhood kids to help with Michelle’s garden and organizing poetry jams on Tuesday nights. But Quinn warns: “You also have to reward the people that have put you there.”

She says that when Washingtonians read about White House events but don’t know anyone who’s going, “people sort of say, ‘They’re not interested in being part of Washington.’” (Translation: Some invites would be nice.)

Of course, the administration folks do get out and about. They can be spotted dining in discreet corners of restaurants like the Blue Duck Tavern, Café Milano, and Central or stopping by events at the hip new W Hotel, with its stunning panoramic views of the city. Emanuel went out frequently—grabbing drinks with journalists, bouncing from restaurant to restaurant—before his young family moved to the city last summer after his three kids had finished out the school year in Chicago.

Yet in some D.C. society circles, the perception holds that the Obamaites are uninterested in mixing, and that probably hurt Rogers after the infamous fiasco of having gatecrashers at her first state dinner. The sniping began, and less than two months after Quinn called for her ouster in a Post column, Rogers resigned.

Washington practically requires a scapegoat, and when things aren’t going well, the Chicago advisers bear the brunt of the criticism. As health care reform slogged on earlier this year, the cable chatterers began calling on Obama to unload his hometown crowd, and editors ordered up political obituaries. Of course, as the president’s political fortunes improved, so did the mood, but the message was clear: No one in the nation’s capital is going to cut them any slack.

Washington, some Chicagoans are learning the hard way, can be a tough town.

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