The pepperoni, sausage and veggie pizzas were shrink wrapped, vacuum packed in dry ice, and 600 miles from home. But, man, were they good.

Darienne Page, the pretty 28-year-old White House receptionist, whose face is the first guests see when they enter the West Wing—and who sits mere feet from the Oval Office—got the idea to order Giordano’s last July. Her boyfriend, a fellow Chicago-to-D.C. transplant, had just taken a job with the Department of Transportation and was feeling homesick. Page searched online for a little reminder of the Windy City and found that the Chicago deep-dish landmark—which had been their date-night joint for pizza and wings after long days campaigning—ships nationwide.

“But when I started telling everyone about it, everyone wanted in,” says Page (whom the president has nicknamed ROTUS, for Receptionist of the United States). “So I ended up ordering six.”

Another junior staffer found a mom-and-pop grocery in northeastern D.C. that sells 312 beer, from Chicago’s Goose Island Brewery, and Page hosted a get-together for appreciative young colleagues at her apartment. Then they did it again, this time at her friend Ian Adams’s pad.

“I tried to cook the pizza, and I think I let it defrost for too long, because it got a little soggy and the bottom ended up falling out of most of it,” says Adams, a 25-year-old native of Geneva, Illinois, who works in the White House as the executive assistant to the director of scheduling and advance. He adds happily: “So I still have some Giordano’s in my oven every time I open it.”

Such is life for the troop of Chicagoans who moved to the nation’s capital to work in President Barack Obama’s administration. (Though no one knows the precise number of Chicago expats in D.C. under Obama, Katie McCormick Lelyveld, the press secretary for the First Lady, says there are about 20 of them in the East Wing and West Wing alone, and many more scattered throughout the agencies.) They are making their way in a transient town that can be tough for newcomers and outsiders, putting their stamp—equal parts Midwest friendliness and hard-charging Chicago politics—on Washington, while Washington quietly shapes them as well. And, of course, they are finding that, like the scent of Giordano’s deep-dish that wafts into Adams’s kitchen each time he uses his oven, a faint thread of Chicago still winds its way through almost everything they do.

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Chicagoans occupy positions of power throughout the administration, from David Axelrod in the West Wing to Arne Duncan in the Department of Education to Susan Sher, Michelle Obama’s chief of staff. The First Family even dines on food prepared by a Chicago native and University of Chicago grad, Sam Kass, who worked as a line cook at Avec before going to Washington with the Obamas.

When the Obama crowd began arriving in town just days after their historic victory in late 2008, they became members of the latest administration to try to fashion some semblance of home in a city best known as the marble-and-monument-flecked backdrop to a massive bureaucracy. Every new president sets his own tone, and every group of eager staffers takes to Washington with varying degrees of success.

Jimmy Carter rolled in from Plains, Georgia, and his circle’s small-town style was initially exotic. He was a peanut farmer, an aloof and moralistic figure, but his young staff quickly keened to the city’s social scene and began popping up in the gossip pages of The Washington Post. Ronald Reagan rode in from the West, the first president to imbue Washington with a sheen of Hollywood glamour.

Bill Clinton and his rascally brigade had a more difficult time. The blue-blooded Washington establishment viewed the baby-boomer president and his young hands from Arkansas as lowbrow riffraff; Bill and his wife, Hillary, in turn, scoffed at what they viewed as the establishment’s elitist Georgetown salons. George H. W. Bush was a Washington longtimer, while his son, George W., wanted nothing to do with the city and behaved accordingly. He went to bed early and rarely ventured out, and his staff followed suit—a loyal cadre of Texans who wore their outsider status as a badge of honor. They holed up in Virginia towns like Alexandria and McLean, preppy suburbs of D.C., and never bothered to make Washington their own.

But the members of the “Chicago mafia,” as this new group is frequently called, are different—both newcomers and yet somehow familiar. Chicago has long had a presence in Washington. The Illinois congressman Dan Rostenkowski headed the powerful Committee on Ways and Means, and when Morton’s of Chicago decided to open its second location, Rosty persuaded his good friend Arnie Morton to bring his steak house to D.C., where it still hosts Washington’s power players. More recently, Rahm Emanuel, Chicago’s native son—who has declared his ambition to be mayor of Chicago one day—was on track to become the first Jewish Speaker of the House before Obama tapped him his chief of staff.

“Everyone here is always welcomed by the Washington establishment, because the Washington establishment thrives on change,” says Sally Quinn, a Washington Post writer who is herself an entrenched part of the establishment and a frequent Georgetown hostess. “If people had their own way, every president would have only one term so you could have new blood all the time. And people also love power and access to power, so they’re thrilled to have all these new people in town.”

At least, they are at first—but more on that later.

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Photo Illustration: Sean McCabe

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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Congressman Mike Quigley was standing in a little row house in the shadow of the Capitol, reciting lines from Mike Royko’s Boss, the bestseller about the late mayor Richard Daley: “But you could always tell, even with your eyes closed, which state you were in by the odors of the food stores and the open kitchen windows, the sound of the foreign or familiar language, and by whether a stranger hit you in the head with a rock.”

No one clocked Quigley with a rock, but the Chicago congressman could have been forgiven for thinking that he was in his hometown. Behind him, a long table was filled with all the trappings for Chicago dogs: poppy-seed buns, slippery grilled onions, freshly chopped white onions, electric-green relish, thick quartered pickles, sliced tomatoes, juicy hot peppers, celery salt, mustard, and, of course, an aluminum tub piled high with all-beef dogs. In fact, Quigley was playing host to a fundraiser—a suggested $1,000 donation bought Chicago dogs and the chance to schmooze the congressman from Illinois’s Fifth District, Emanuel’s replacement. But Quigley was quick to point out the flaws with his Chicago-cum-D.C. spread.

“This is like a B,” he said, offering a grade. “But for D.C., it’s not bad. You’re supposed to have a big pickle on your hot dog, you’re supposed to have mustard—but for these people, heathens that they are, we put ketchup on the table. For the D.C. people.”

So where in Washington could the congressman close his eyes and know exactly where he was?

Quigley shrugged. “The floor?” he offered. “The House floor?” Then he resumed talking smack about his temporary town. In Washington, transience can often seem like the town’s most permanent trait. The adjustment can be tricky for someone from Chicago, where roots run deep. “You have third-generation Cubs and Sox fans in Chicago,” says Quigley’s press assistant, Ben Strauss, 24, who moved from Lake View last summer before landing a job with the congressman. “You don’t have third-generation anything in D.C.” (Redskins fans might disagree.)

“There isn’t the same vibrancy in D.C.,” Strauss continues. “People come to D.C. to work. To live in D.C. is to work. You can be friends with someone in Chicago for years and not be quite sure what they do. In D.C., the first question out of your mouth is, ‘What do you do?’ You never leave home without a business card. You can never really relax.”

The Chicago crew is still struggling to find a favorite restaurant or a deli that can rival Axelrod’s beloved Manny’s on South Jefferson Street. (Axelrod recently had an infusion of corned beef and turkey legs shipped from home.) But Union Pub, an ersatz Bears bar on Capitol Hill, frequently pops up as a favorite Chicago hangout, a place where administration staffers are sure to spot a familiar face.

“They play the Chicago Bears theme song every time the Bears score a touchdown,” says 24-year-old Luke Rosa, a Lincoln Park native who just finished an internship in the White House and is now looking for a job while keeping busy with freelance work for the administration. “Everyone is in Chicago jerseys. It’s pretty much like being in a Chicago bar watching a Bears game.”

Beyond sports, food provides a link to home for many Chicagoans. There’s a Secret Service agent from Chicago on the president’s detail who is also an amateur chef, and he makes deep-dish for hungry colleagues. Susan Sher’s husband was invited to the first annual White House seder last year and came bearing macaroons from Manny’s—“because he felt only those were the best,” Sher says, laughing. They attended again this March, and about a week before, one of the Secret Service agents from last year saw Sher and asked if she’d be bringing macaroons. Yes, indeed.

Sam Kass, the 30-year-old White House chef with a smooth shaved head, plummy lips, dimples, and an easy smile that landed him on People’s “Most Beautiful” list last year, has also been slowly adjusting to his new home. He seems to have cracked the Washington-as-outsider code, carving out a niche for himself by simply doing his own thing—getting to know his new neighborhood, meeting some nonwork friends, throwing himself into his East Wing job—and neither shunning nor coveting the spotlight.

Kass also carries the title food initiative coordinator, which means he handles the garden on the South Lawn and Michelle Obama’s extensive food and health programs. He once cooked for the Obamas in Chicago; now he brings inner-city kids in for tours of the White House garden, and he accompanied the First Lady when she helped open a farmers’ market in downtown Washington last fall.

Kass can already rattle off a few of his favorite D.C. restaurants: Founding Farmers, Zaytinya, anything by the famed chef José Andrés. “I love Good Stuff,” he says, referring to the quirky burger joint owned by the former Top Chef contestant Spike Mendelsohn.

Standing in the South Lawn garden one morning, Kass showed off the White House beehive—a cluster of large pastel-colored boxes stacked four high atop an elevated platform, tied down with thick yellow straps so the whole thing doesn’t blow away when the president’s helicopter touches down.

“It’s really good honey,” Kass said. A little of Chicago began to creep into his accent as he continued: “I’ve tasted lots of honey. I’d put my honey up against anyone’s.”

Although he was talking about honey, he could have been talking about anything, really—his new life in the nation’s capital, the unforeseen pressures of his job, the little ways in which he’s trying to change Washington while the city slowly changes him as well.

He paused for a moment and smiled. “Yeah, bring it.”

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