A surprising number of the Chicagoans I met in Washington, on hearing of my interest in their growing ranks within the Obama Administration, delivered the same punch line to a well-worn story about home. Sixty years ago, when a future U.S. congressman and federal judge named Abner Mikva tried to volunteer at his South Side ward office, the boss there asked him, “Who sent you?” After the young Mikva admitted no one had, he was rebuffed: “We don’t want nobody nobody sent.” By reciting this kicker, the Chicagoans were staking their own claim to the city’s pugnacious political history while at the same time implying they had traveled far from that world. It was a way to say they had come out of Chicago with all the valuable lessons and none of the taint. Barack Obama himself sometimes proclaimed on the campaign trail, “Nobody sent me,” announcing both his ties to his adopted city and his arrival as a force for change.
Over the past year and a half, the administration’s Chicago roots have been credited with just about all its failures and accomplishments, the word “Chicago” serving as shorthand for everything from extremism to incompetence to conciliation. The core group of Chicagoans close to the president, all of whom worked for Mayor Richard Daley, have been accused of tone-deafness and insularity. Within the course of a few weeks earlier this year, the Beltway punditry issued competing calls for Rahm Emanuel to step down as chief of staff and to take over the reins in the White House; cast as a bat-wielding Al Capone, he was seen as both the administration’s corrupter and its savior. The passage of health-care reform, in March, was hailed as the triumph of a “Chicago Way,” just as two months earlier the bill’s impending death had been chalked up to the Obama team’s provincial innocence.
In reality, this group of Chicagoans has hardly distinguished itself from past administrations. They are eager to cozy up to power when it suits their interests; they have pointedly given little offense, social or ideological, to the Washington oligarchy and the system over which it presides. Progressives who back in December felt betrayed by compromises in the health-care bill and other unfulfilled promises now are thrilled at the passage of legislation in any form, their elation made possible only by their diminished expectations. An administration that seemed adrift for its first year—that often appeared out of touch and unable to communicate what it stood for—may have emerged from Chicago with some of the taint and not enough of the hard political lessons.
When I spoke to Mikva, long a friend and mentor to the president, I asked about the appropriation of his ward-boss anecdote. “Barack took it on as if it happened to him,” Mikva said, his voice betraying just a hint of irritation. “I had to remind him where he heard the story. I had to tell him that it was my story, and it really happened.”
One of the first Chicago transplants I met in Washington was Tim Tuten, a friend of my brother’s who had recently been named to a communications job in the Education Department. Tim, who is forty-nine and co-owns a music club on the North Side of Chicago called the Hideout, belonged to a cadre of ex-campaign workers and junior appointees who were re-creating (and redefining) their Chicago networks in the capital. Staffers from Obama’s U.S. Senate campaign, many of whom were now scattered throughout various departments, told me they had begun to reconnect. Another group—including several graduates of the University of Chicago Lab School, the high-end private school in Hyde Park that the Obama girls attended—was also gathering biweekly in what one member described as a kind of salon. “Anyone passing through from Chicago stops by,” explained Kareem Saleh, a Georgetown University law student who served on the economic transition team after the election. As for Tim, he had been a teacher and administrator in the Chicago public-school system; now he was one of a dozen or so Chicagoans who worked under Secretary of Education Arne Duncan, formerly the Chicago superintendent of schools. In his first weeks in the capital, Tim said, he ran into a friend from home at the White House, fell in with a new circle of Chicagoans at a barbecue in southeast Washington, and attended a rooftop party at the home of Peter Cunningham, who had worked for both Daley and Duncan in Chicago and is himself currently at the Education Department. Other guests at the rooftop party included Duncan, various administration staffers from Chicago, and even members of Wilco, the popular Chicago-based band.
“You might see Valerie Jarrett at the rooftop of the W hotel,” Kareem Saleh said of the senior White House staffers gathering around town. “We’re more punk-rock hipster bars.” On a Tuesday in mid-July, on a night when Charley Pride was a last-minute addition to an “Evening of Country Music” at the White House, I met Tim Tuten at one of these bars, a place called Wonderland, in Washington’s Columbia Heights. We were joined by several other Chicago transplants, including Liz Drew, who was waiting for clearance to start a job at the State Department, and her boyfriend, Dan Lurie, a former official of the Chicago Transit Authority who had landed in Housing and Urban Development. “It hasn’t sunk in that we left home, because we have so many friends here. We still see the same faces,” Liz said. She had attended the Lab School and had worked on Obama’s Senate staff with another Chicagoan at the table, David Le Breton. They counted off numerous friends in the administration—the Lab alumnus who was the politically appointed White House sous-chef; the presidential campaign photographer, another Lab Schooler, now in the Energy Department; Michael Strautmanis, a Michelle Obama protégé in Chicago who had become Valerie Jarrett’s chief of staff. Tim and Dan knew each other not from a campaign or high school but from the Chicago music scene. Back home they never even discussed politics. Unlike in Washington, Tim noted, “people in Chicago are into so many different things: city history, architecture, arts. Being on the North Side, I’m afraid that if I ask about people’s politics I’ll find out that the person I sort of like is a Naperville Republican.”
At the beginning of every new administration, of course, there is a hometown crowd that drafts behind the president into Washington. One wouldn’t wish it any other way; an effective White House must include staffers who know the president’s temperament and principles, people who have long spoken to him as a person rather than as an icon. But just six years ago, Obama was still a state senator, and many of the young Chicagoans in today’s administration were working intimately with him at all hours of the day. Shortly after Liz Drew graduated from college, in 2003, she left a message at Obama’s law office asking if she could serve on his U.S. Senate campaign; Obama phoned back the next day to offer her a position. Tarak Shah, who now holds a post at the White House Council on Environmental Quality, received his personal call from the state senator in his University of Illinois apartment. The candidate took Dan Lurie out to breakfast after the two were introduced on a downtown Chicago street. “I’m still in awe that I had the president’s cell-phone number,” said Juleigh Nowinski, a senate staffer who worked at Health and Human Services until this May. At early fund-raisers, Liz would invite her friends to fill out the sparse crowds, thinking that Obama wouldn’t notice. “Liz, I saw a lot of your friends here again,” he said with concern after one event. “Does that mean we didn’t raise very much money?”
Regardless of where they have ended up in the administration, the junior staffers all said they were in Washington not to work in government but to serve the president. They spoke of Obama’s agenda with an earnestness that, as one of them put it, at times veered into “some cheap West Wing vision of how exciting the job is.” In many ways, they represented the most ardent of the campaign’s rally-goers, the most dedicated of the ground troops, and generally they were to the left of the president politically. Often I heard staffers say they were willing to tolerate Obama’s reliance on political operatives and what seemed like daily concessions to both Republicans and conservative Democrats; they reasoned that these allowed him to accomplish his goals. As several people explained to me, they believed Obama to be a progressive on the inside, even if his outward actions suggested otherwise.
“I can’t be objective about Barack. For a long time he was the most important person in my life. I trust he’ll do the right thing,” Liz said. “People think of him as cool and calculating, but I know his motivations. He thinks tactically, but I never question his motivation.”
“It’s not an accident that a lot of the people Barack chose worked for Rich Daley,” Frank Kruesi told me. Kruesi, who has himself worked for Daley since well before the mayor took office in 1989, met me at a food court in a shopping mall two blocks from the White House. He had been the president of Chicago’s transit system—before stepping down, in 2007, during an outcry over shoddy service—and he now ran the city’s lobbying office in Washington. (Until recently, Kruesi’s wife was Daley’s scheduler, and several Chicago natives told me that if you upset Frank, you could forget about an appointment to see the mayor.) Kruesi said of the Chicagoans new to the capital, “As far as government policy and politics, I don’t think they could have been trained by someone better. It’s a strong alumni group.”
Michelle Obama and Valerie Jarrett have both said they took jobs at City Hall in order to dedicate themselves to “public service.” It is common in Chicago for people to shift between the private and public sectors and, if liked by Daley, to take on a wide range of roles for the city. Jarrett, for instance, served as Daley’s deputy chief of staff, the commissioner of the Department of Planning and Development, and the chair of the transit-system board before she returned to the private sector. Prior to his congressional run, Rahm Emanuel worked at the Chicago office of a large investment bank, earning $18 million in just two and a half years, a windfall due largely to the network of clients he tapped from his days in the Clinton White House and the Daley City Hall. Few Chicagoans would think of a job at City Hall as an opportunity to “give back.” Lynn Sweet, the Washington bureau chief of the Chicago Sun-Times, told me with a laugh, “You might think, That person has a good pension, or Maybe they know someone, or They don’t have to work very hard. But you’d never say, It’s public service. It’s not the Peace Corps.”
Many of the Chicagoans now in Washington, though they may have close ties to Mayor Daley, are not the machine operatives that conservative critics tend to envision. Neither are they the former political radicals and civil-rights activists who settled on the city’s South Side, nor even the reform-minded independents who once dominated Hyde Park politics. Indeed, in his 1996, 2000, and 2004 campaigns, Obama ran independently of Daley but never as an anti-Daley candidate—illustrating the careful balancing act that must be executed by a Hyde Park politician with greater ambitions. Don Rose, a veteran political consultant and organizer in Chicago, described Jarrett, David Axelrod, Duncan, Michelle Obama’s chief of staff Susan Sher, and other members of the administration who worked for Daley as technocratic apparatchiks; they were the mayor’s loyal managers and policy people. Rose said that Leon Despres, Hyde Park’s independent alderman from 1955 to 1975, had a name for their type: curiae. “He used it in the medieval European sense of one who attends a ruler and is delegated for numerous sequential tasks. I believe Despres spoke specifically of the Medicis.”
For nearly two hours, as the food-court tables around us filled with the lunch crowd and then emptied, Kruesi recounted his boss’s two decades as mayor in the most glowing terms. He dismissed as “cynical” the view that Daley had abused his power—that, in other words, he was anything like his father, whose mayoralty lasted from 1955 to 1976, when he died in office. “There’s this talk of unanimous votes in the city council, of Daley with his thumb on everybody. Nonsense.” Kruesi explained that people didn’t see the real work the mayor did to win over critics and to reach consensus. “It’s like a duck gliding effortlessly along the water. When you look under the water, you see his feet paddling furiously. That’s part of the secret of Rich Daley. He works so hard, and it looks so effortless.”
It’s true that Chicago no longer has a political machine as it existed under the first Richard Daley, with tens of thousands of patronage workers beating the bushes to deliver the vote. Campaigns in Chicago, like elsewhere, now depend less on ground troops than on corporate donations and television ads; the spoils come less as patronage jobs than as government contracts. Yet the city remains a kingdom of pragmatic dealmakers, of politicians who view ideology as weakness. During his years in office, the current Mayor Daley has personally appointed to the city council thirty-five aldermen, nineteen of whom are still serving in the fifty-member caucus. He has built strong ties to the city’s business community and the more conservative suburbs. He has taken direct control of the schools and public housing, while at the same time privatizing numerous public services. In short, like his father, he has imposed his vision on the city. During the planning of a downtown museum campus, in 2003, Daley ended debate over whether the city had the authority to close a private airport on the proposed site by sending over bulldozers late one night to tear up the runway. By way of explanation, the mayor said he was protecting the Loop from terrorist attack.
Daley’s long tenure and many successes stem in part from a willingness to embrace social change in ways his father refused to do, such as hiring African Americans and supporting gay rights. “Richie is a very smart person,” Abner Mikva said. “He has some of the deeses and doses of his father. But in addition to street smarts, he has an awareness of what’s going on in the city that his father didn’t.” The independent political movement that formed in opposition to the first Daley has also mostly dissipated. There are still a few causes that mobilize the small number of reformist aldermen—fighting the mayor’s plan to lease the municipal water system, for example—but progressive politicians largely have had little to rally around since they helped to elect Harold Washington, the city’s first black mayor, in 1983. “Daley hasn’t ignored the independent movement; he hasn’t dissed it,” Kruesi said, illustrating the word by slapping an imaginary face with the back of his hand. “It’s hard to demonize someone who is responsive and able.”
Many of the onetime reformers are now part of Daley’s network. Marilyn Katz, who along with Bill Ayers and Bernardine Dohrn was a member of Students for a Democratic Society, runs a communications firm and works closely with the mayor. She explained that Daley’s father despised her and her SDS compatriots, but that the son “looks under the police record or the rhetoric and asks, ‘Are you working to build this city?’” Katz has been friends with Obama since the early 1990s, when the two of them worked together on community—development issues and occasionally played golf. She said that Daley and Obama both learned a brand of transactional politics in Springfield; as state senators they made it a priority to get to know downstate Republicans and to work across the aisle. “Politically as well as culturally, Obama is moderate, a progressive moderate,” Katz told me. “I am by nature a radical, an outlaw. But there’s not really a radical bone in Obama’s body. It’s pretty funny.”
I caught a glimpse of Chicago’s remaining South Side independent movement last Fourth of July, at a parade marching up one of Hyde Park’s main thoroughfares. Leading the procession was the neighborhood’s alderman of nineteen years, Toni Preckwinkle, who was dressed as the Statue of Liberty in a seafoam-green gown. On previous Independence Days, she had been accompanied by State Senator Barack Obama decked out in a George Washington costume. But this year she was trailed by twenty or so supporters, each in a blue T-shirt advertising her run for president of the Cook County Board of Commissioners, the county’s highest political office. (In February, she won the Democratic primary in an unexpected landslide.) The parade also included a marching band and cheerleaders from the local public high school I had attended, neighborhood business owners, and several African-American cowboys laterally cantering their horses. Somewhere in there, a small car inched along with two giant photographs of Sam Ackerman masted to its roof. Ackeman had been the president of the Independent Voters of Illinois–Independent Precinct Organization, once one of the most influential political groups in the area. But as with Ackerman—an urn containing his ashes rode inside the car—the IVI–IPO’s influence was mostly a memory. As we watched the proceedings, my wife pointed to a man stepping out of a dark SUV on an adjoining street. It was Jesse Jackson Jr., the neighborhood’s eight-term congressman and a vocal critic of the mayor. Jackson’s reputation had been tarnished recently when he was caught up in the scandal surrounding then-governor Rod Blagojevich, who was taped trying to sell Obama’s Senate seat. Jackson grabbed a coffee at a Starbucks and then stood alone, watching for a minute as the parade shuffled past.
Although Chicago remains one of the nation’s most racially divided large cities, it is also a city where African Americans have long operated in the highest reaches of power. “It’s the contradiction embedded in segregated Chicago: elites across racial lines are used to working with each other,” Michael Dawson, a professor of political science at the University of Chicago, told me. Illinois is one of the few places in the country where black politicians have consistently built statewide coalitions. The first African American elected to the Congress in the twentieth century, Oscar DePriest, was a Chicagoan, and three of the four African Americans to serve in the Senate since 1900 have been from the city’s South Side. As surprising as it may be that we have an African-American president, it is less of a surprise that he should come from Chicago.
But none of Obama’s bids for office began as a popular cause within the city’s black community. He turned first to a small network of African-American business leaders, many of whom were close friends from Hyde Park. These businesspeople—among them John Rogers, the ex-husband of former White House social secretary Desiree Rogers and the founder of one of the largest black-owned investment firms in the country; Marty Nesbitt, who owns the Parking Spot, an off-airport parking company; and Valerie Jarrett—provided Obama with a financial base and eventually helped him to access the real money in the city, the white Lakefront Liberals. Consequently, the Obama Administration does not include Jesse Jackson Jr., Bobby Rush (who handed Obama his only electoral defeat, in the 2000 congressional race that saw Obama called “the white man in blackface”), or any other member of Chicago’s South Side political apparatus.
When I was in Chicago last summer, Marilyn Katz took me around several South Side communities where Jarrett had helped tear down and replace public–housing high-rises with mixed-income developments—first as the city’s chief development official and then as the CEO of a for-profit real estate firm contracted to oversee the city’s public-housing development deals. (One of the worst of the former high-rise housing projects had been named for Jarrett’s grandfather, Robert Taylor, the first African American to head the Chicago Housing Authority.) Of those I talked to, many echoed Katz’s point about Jarrett and the other Chicagoans in D.C.: They knew urban issues. As residents of Hyde Park and the South Side, they had firsthand knowledge of inner-city poverty; they had experienced the city’s complex interplay of racial strife and class conflict. It is in large part because of this background that many Obama supporters assumed his team would dramatically undo Bush-era policies through sweeping reforms; it is this same background that stokes opponents’ fanciful notions of foreignness and leftist extremism, such as Newt Gingrich’s claim that Obama is running a “secular, socialist machine.” Privileged and relatively wealthy, with close ties to others in Chicago’s political and business establishment, theirs is actually a complicated urban milieu that defies political caricature.
Kwame Raoul, who was named to the state-senate seat vacated by Obama in 2004, grew up on the same Hyde Park block where, in 2005, the Obamas bought their six-bedroom home, a street on which John Rogers lived and which is named in honor of Rogers’s mother, a distinguished Republican judge. Additionally, Raoul attended the Lab School—where Michelle Obama, Jarrett, Susan Sher, Marty Nesbitt, and John Rogers all recently served on the board of directors. (When I met with Rogers at his downtown Chicago offices overlooking Millennium Park, he remarked, “It says something about parents who choose to send their kids to Lab: You’re a progressive thinker. You believe in Hyde Park. You believe in inclusion and fairness.”) Not surprisingly, some of the same local black business leaders who initially helped Obama also backed Raoul. And Rogers and Arne Duncan, one of Raoul’s high school basketball teammates, were among the first prominent Chicagoans to endorse him.
After Raoul was appointed, another aspirant to the seat, Will Burns, came over to offer congratulations. Burns, who is now a state representative, is another young African–American politician with close ties to Obama, but he had moved to the neighborhood from Cleveland only when he began school at the University of Chicago. Burns looked at Raoul and his team of supporters and said, “I guess I should have gotten a Lab School mafia, too.”
I spoke with Carol Moseley Braun, the former senator and presidential candidate. (“That lasted for a hot second,” she said of her 2004 run.) As a recovering politician, she told me, she rarely gave interviews and was focusing her energies instead on an organic food company she had started in 2007. When I asked about the similarities between the rise of Barack Obama and her own rise from Hyde Park and the University of Chicago law school, she dismissed the comparison as one of apples to oranges. There was a fundamental difference, she believed, between the political roots of Obama, Raoul, and their ilk, on the one hand, and the previous emergence, on the other, of herself and of Harold Washington, another Hyde Park resident who served in the Illinois senate before being elected to higher office. “The independent movement was not a Lab School movement,” she said. “It was a civil-rights movement. It came from an entirely different place. Just look at the tuition.”
Last summer, the Department of Education hosted a weekly reading series on the plaza in front of its headquarters. Various administration officials, including Rahm Emanuel, David Axelrod, Valerie Jarrett, and U.N. ambassador Susan Rice, joined Secretary Duncan at the events to read stories and distribute free books to local children. When I arrived at one of these “Read to the Top!” programs in July, a woman in a pantsuit was asking questions into a cordless microphone. “What is chartreuse?” “How many $5 bills can you get out of a $20 bill?” The mostly black and Latino grade school students, who sat in front of her cross-legged, raised their hands and shouted clamorously; correct answers were rewarded with stickers. Behind them sat a crowd of seventy-five or so, many of them older African Americans, volunteers in a foster-grandparents program. They were there to see the day’s guest reader, Marian Robinson, Michelle Obama’s mother.
After Duncan arrived with the “first grandmother,” he explained to the students that Mrs. Robinson’s son was not the president but a man named Craig Robinson, “one of my closest friends.” Duncan and Craig Robinson got to know each other as teenagers on South Side basketball courts. Duncan went on to play for Harvard, Robinson for Princeton. One of Robinson’s teammates was John Rogers, whom Duncan had idolized back in high school at Lab. When Duncan returned from a stint in an Australian professional-basketball league, he ran several education programs in disadvantaged communities for Rogers and then (with his sister) operated a Rogers-funded small public school in North Kenwood, a neighborhood adjacent to Hyde Park. The new school was just one element of North Kenwood’s planned redevelopment, with the larger effort being the rebuilding of much of the neighborhood’s housing stock—one of the development projects Valerie Jarrett had been tasked with orchestrating.
When Marian Robinson finally took the stage, the older women in the audience stood, wobbly legged, to better see her; employees on lunch break from other federal buildings flocked around the plaza’s perimeter. Robinson read The Napping House, a story about a child and several creatures who fall asleep atop a slumbering grandmother. When Robinson finished the book, Duncan suggested that students ask her questions. A girl with a bit of a stutter asked how the president and first lady met. Robinson said, “The story is, they were working together. Didn’t she become his mentor or something?” Then a boy walked close to the small stage, only a few feet from Robinson’s face, and asked, to laughter, “Are you rich?” The first grandmother, who had already described the White House as larger than anything she was accustomed to, told the child that she was not.
Several people, in discussing Obama’s Chicago circle of African-American confidants, pointed out that Michelle Obama alone had not come from a family of significant means. Her father had worked at the city’s water department, for many years doing so with debilitating multiple sclerosis. Marian Robinson was a secretary at a bank until 2007, when she retired to help with her granddaughters. And for high school Michelle went not to Lab but to one of the city’s public magnet schools. Yet Carol Moseley Braun assured me that the family nevertheless must have wielded some influence within the city’s political power structure. “For Michelle Obama’s father to work in the water department under the old man Daley, he had to have been connected, period. Nobody got a job with the city that didn’t come through the Chicago political machine. That was as incomprehensible as walking on the moon without an oxygen mask.”
Mrs. Robinson’s young inquisitor, still not satisfied, took another step forward. “You got a lot of money?” he asked. There were still gee-whiz laughs from the audience but also some uneasy seat-shifting. “Are you angry?” Robinson asked back. But then the first grandmother collected herself and explained that you can be happy if you earn enough money just to pay your way. She said it felt overwhelming to have a daughter married to the president. “Especially when you come from the South Side of Chicago, go to public schools, live an ordinary life of going to work and making a living.”
On an evening when the president held a prime-time news conference to discuss health-care reform, I attended a “Celebrate Chicago in D.C.” fund-raiser for Illinois Congressman Mike Quigley. The event was held at the Capitol Hill outpost of the Billy Goat Tavern, a Chicago bar and grill famous for the curse its original owner laid on the Chicago Cubs, in 1945, when his goat was kicked out of a World Series game at Wrigley Field. Quigley had been in office just three months, having won the special election to fill the seat vacated by Rahm Emanuel. Quigley’s North Side district previously was represented by quintessential insiders—Emanuel, Rod Blagojevich, Dan Rostenkowski. But Quigley, a Cook County commissioner who described himself to me as “fiscally conservative but very liberal on social issues,” ran on his record as a reformer and environmental activist. With twelve Democrats on the ballot, he was able to cobble together enough support to squeak by in a low-turnout primary (winning the Democratic primary in Chicago being tantamount to winning office).
The Chicagoans who had come to the Billy Goat to curry favor with the new congressman were almost all young white men in dark suits. One of them told me that he managed the political-action committee of a large Chicago-based law firm. During the special election, he said, it seemed like even the associates at his office each had a different friend in the race. “One lawyer sent me an email about a politician who did us a huge favor and how we should do something for him in return. I’m like, ‘Whoa. Let’s not do that.’” I also heard an attendee named Chris Kozicki explain to Dan Lipinski, another congressman there from Chicago, that Bridgeport, the traditionally Irish neighborhood where both Mayor Daleys were raised and where Kozicki lived, is now 30 percent Chinese. Kozicki worked in Chicago’s City Hall for thirteen years before taking a job with a maker of steel screens used to cover abandoned buildings. It was his first extended business trip to the nation’s capital, and he had already scored meetings with HUD and D.C. city officials. His Chinese neighbor, he’d heard, had gotten one of “those mail-order brides.” The woman eventually left her husband, but the family she brought over from China had stayed. “They’re always out there gardening,” Kozicki said.
 In 2004, Lipinski was teaching political science at the University of Tennessee when his father, an eleven-term congressman representing southwestern Chicago, withdrew from the race for his twelfth term after he had already won the Democratic primary. Then, in what is a dispiritingly common Chicago move, the elder Lipinski persuaded local Democratic Party officials to put his son’s name on the ballot in place of his own.
Mike Quigley arrived late, rushing over from the Capitol and immediately removing his jacket before pushing into the crowd. An ice-hockey fanatic, he had skated that morning with a group of Canadians who were filming a reality show called The Buried Life, which, I was told, combined elements of a “bucket list” with the idea of “paying it forward.” Quigley is fifty-one, short, and trim, with a rounded Irish nose and an inability to remain still. When we chatted, he described the learning curve he faced as a newcomer to Washington. “I owned Cook County as far as institutional knowledge. Here, it’s like transferring your senior year to a new high school. You suddenly have 434 new classmates, and you need to know them all and what they like. That stuff is really important when you’re working with people.” He mentioned the advantages of already knowing the occupants of the White House. “Both Chicago and D.C. are political towns,” he said. “Power is power. Clout is access to power.”
But no city comes close to Washington in its blinding fixation with insider politics. Tarak Shah noted that when he took a break from Obama’s presidential campaign headquarters in downtown Chicago, he would come into contact with “an entire world that wasn’t consumed by politics.” John Schmidt, a Chicago mergers-and-acquisitions lawyer who counseled the city in the privatization of one of its major toll roads, had been Mayor Daley’s chief of staff before going to Washington to serve in the Clinton Justice Department. He told me how on each trip back to Chicago he would become acutely aware of the skewed perspective in D.C., a place where Sunday-morning talk shows are seen as the most important constituency and a press conference announcing the introduction of a bill is considered an accomplishment in and of itself. “I came to think of Chicago as the place where you had to deal with reality and Washington as the place where an artificial media world of the press and P.R. and imagery took on a life of its own,” he said.
When Scott Brown won Ted Kennedy’s Senate seat in Massachusetts, the administration was castigated, perhaps correctly, for having lost touch with the world outside Washington. Soon after Obama took office, Rahm Emanuel moved his family from Chicago to D.C. David Axelrod, the former Chicago Tribune reporter and guru of local politics, started holding Wednesday-night meetings with a group of fellow political consultants in his new Washington home. And Valerie Jarrett, Susan Sher, and Desiree Rogers (up until her recent departure) all lived in the same Georgetown apartment, a residence they playfully refer to as “the dorm.” The Obamas themselves initially planned to return regularly to their South Side home, calling it their Kennebunkport, but they have made just one overnight trip back, in February 2009.
Quigley worked long hours—incredibly, he did not even keep an apartment in Washington, instead sleeping in his office every night—and he already saw that almost all socializing there was some form of politicking. But his family remained in Chicago, and as a congressman he was able to fly back home on weekends. “I won’t lose my bearings, because I won’t forget the street-level stuff,” he said. He explained how Republicans had tried to push through a record number of votes during one of his first days on the Hill. One veteran Republican pointed directly at Quigley and began yelling at him. “I said back to him, ‘I’m from Chicago, we can do this tomorrow,’ ” Quigley told me. “The political tough guys aren’t going to intimidate me. I had people in Chicago physically challenge me.”
In September, two weeks before the city of Chicago presented its case to the International Olympic Committee for hosting the 2016 Summer Games, the White House held an event on the South Lawn to promote the bid. A balance beam and mats had been placed on the grass beneath the Oval Office windows, not far from the swing set that had been installed in the garden for Sasha and Malia. With a jaunty “Stars and Stripes Forever” playing in a loop, children from nearby Lake Ridge and John Philip Sousa middle schools joined officials from Chicago’s City Hall and the Obama Administration to watch Olympians demonstrate proper technique in judo, fencing, and gymnastics.
The president would fly to Copenhagen to lobby in person on Chicago’s behalf, joining Michelle Obama, Valerie Jarrett (who had worked on the bid herself, first in Chicago and then as the head of the newly created White House Office on Olympic, Paralympic and Youth Sport—a possible conflict of interest that required a special ethics waiver), Arne Duncan, Transportation Secretary and former Illinois congressman Ray LaHood, and Oprah Winfrey. Chicago would finish fourth among the four finalists. When the IOC announced its decision, there was jubilation on the streets of Rio de Janeiro and in the halls of The Weekly Standard, according to a blog post by the magazine’s editor entitled “Chicago Loses! Chicago Loses!” Obama’s right-wing critics managed to see in the Olympics defeat a rejection not only of the administration’s mobbed-up hometown ties but also of its entire big-government liberal agenda. “Game over on Obamalympics. Next up, Obamacare,” tweeted Michelle Malkin.
 Despite the Olympics loss, Obama himself may actually have escaped with a victory, by avoiding the prospect of very serious conflicts of interest. The businessmen and politicians on Chicago’s Olympic Committee bundled at least $1.95 million for Obama’s 2008 presidential election, and many members of his staff still have significant financial interests in the city. He also will not have to spend the next six years under attack at every whiff of corruption emanating from any Olympics-related projects.
But on that sunny fall day, expectations for Chicago’s bid remained high. Daley was first to address the crowd. Flanked by the first couple and the track star Jackie Joyner-Kersee, Daley looked squat, flushed, and uncomfortable. He spoke about his deep desire to showcase Chicago’s landmarks and ethnic neighborhoods, and he stumbled through an explanation of what Chicago thinks about when it thinks about the Olympics, which is Jesse Owens and Ralph Metcalfe—“two young men from the South Side of Chicago who went to Germany in the 1930s. Their race was not popular at the time, in the city and the country.” (Frank Kruesi, Daley’s aide-de-camp of many years, told me how people often failed to realize that the mayor’s apparent inarticulateness was a sign of “something more profound. He thinks so fast that his thoughts are way ahead of what he says.”)
After Barack and Michelle Obama took turns extolling Chicago’s charms, they left the lectern to watch the Olympians perform. At the judo mats, as the athletes flipped one another repeatedly, the president, his jacket off, stood with an arm looped casually around his wife’s waist. When the couple moved over to the fencers, the president picked up a foam sword and jabbed it into the first lady’s belly.
At the same time, the dozens of other Chicagoans on the South Lawn—the mayor’s people and those who were now the president’s—conversed among themselves. Daley and David Axelrod spoke intensely for several minutes, Axelrod hunching his tall frame to position his ear closer to the mayor’s mouth, Daley clapping his hands to underscore his points. Jarrett and Kruesi, who had clashed during their time together at the Chicago Transit Authority, talked amicably, while Obama’s controversial Senate replacement, Roland Burris—small, stoop-shouldered, with a near-constant impish grin—listened in. Congressman Bobby Rush extended a hand to Arne Duncan. Tina Tchen, a Chicago lawyer and Obama fund-raiser now in the White House, cheek-kissed a City Hall friend. Mike Quigley paced near the balance beam. Cindy Moelis and Bob Rivkin, a husband and wife who had worked in city government back home and were currently in the White House and Transportation, respectively, neared the scrum hand in hand. Desiree Rogers, in leopard-print high heels and a short, form-fitting skirt, stood beside her ex-husband, each Rogers staring silently into a BlackBerry.
I was positioned behind the reporter’s rope next to Lynn Sweet, of the Sun-Times. At one point she turned to me and said, “It’s like a high school reunion out there”; she went on to describe the Obama people as “the Daley wing of the Democratic Party.” But if the White House were actually run with the iron first of a Daley, it might not find itself forced into so many disappointing compromises. The Chicagoans in the administration seem to have served a machine without learning how to run one themselves.
Frank Kruesi sidled up, reminding Sweet that he had known her for three decades—longer, he said, than he’d known any other Chicago newsperson. He opened a binder to show her glossy 8 x 10 photographs that the mayor and other city officials had taken beside Janet Napolitano at the Department of Homeland Security. Soon Mike Quigley ambled over, too, and Sweet apologized for not paying more attention to him. The new congressman didn’t seem to mind. He wore chunky black sunglasses that looked like BluBlockers, and I heard him say that the Chicago Blackhawks were playing at that exact moment. He paused as if listening for something far off. “The puck is dropping right—now!”
“I think people will want to do their stint with the Obama Administration, but once that’s done, I think most of them will want to get out of Dodge,” Danny Davis, the six-term congressman from Chicago’s West Side, told me. “The guys had a song they used to sing: ‘You can keep your New York, I’m going back to Illinois just as fast as I can,’” he crooned in a mellifluous baritone. Indeed, many of the Chicago set I met in Washington firmly believed their political destiny lay back home. With “change” on the national level repeatedly undermined by partisanship and advanced only through a near-endless series of painful compromises, progressive politics now seemed to them more plausible—even desirable—on the local level. In Chicago, they already knew all the street names, all the players. Their new jobs had exposed them to best practices from cities around the country, and all the missed opportunities at home suddenly seemed inexcusable. Chicago was just 228 square miles; anything should be possible there. “We don’t want to be in D.C. for the sake of being here, and when the time is right we’ll see if we can go home and make something special happen in Chicago,” one of them told me. (Like everyone who spoke on this subject, this Chicagoan asked not to be identified, since such talk might seem a dereliction of present duties in Washington and an affront to people back home.)
Any plans staffers had to use their Washington experiences and connections to reenter Chicago were at least as far off as the midterm, and perhaps as far off as the 2012 reelection campaign or beyond. Still, speculation about what such a return might entail came naturally. Some imagined themselves in a leadership role with one of the city’s large philanthropic organizations, or possibly one of Chicago’s influential public-private partnerships. There was also much conjecture about the mayoral race in 2011, and who might challenge Daley or rush to fill the vacuum if the mayor chose not to run for a seventh term. (Daley was reelected in 2007 with nearly three quarters of the vote; but, in part because of a fiasco involving the privatization of the city’s parking meters, by last fall his approval rating had sunk to an all-time low of 35 percent.) These Chicagoans shared their constantly amended mental lists of potential mayoral candidates, naming several Hispanic city and state officials, a progressive alderman, a couple of hometown people in the Obama Administration. People had their theories on whether Rahm Emanuel would run if Daley decided not to, but I also heard that Emanuel expected eventually to get his old congressional seat back. One staffer said of a possible Emanuel mayoralty, “I don’t know anyone in D.C. talking about being a part of that.”
For many of these Chicagoans in Washington, Daley’s fall seemed an inexorable corollary of Obama’s rise. Understandably, some of them harbored doubts about whether the Obama Administration actually represented a new direction for the country. In December, William Daley—the mayor’s brother and an Obama backer—wrote in a Washington Post op-ed that the Democratic Party “has a critical decision to make: Either we plot a more moderate, centrist course or risk electoral disaster not just in the upcoming midterms but in many elections to come.” It was a strategy that seemed oblivious to the facts of the past year. The final health-care bill, nothing if not “moderate” and “centrist,” could not win the vote of a single Republican.
Yet Obama himself continues to fill the Chicagoans with hope. His ascent out of local politics, in a city dominated by nepotism and family legacies, for them represented true audacity, the wonder of boundless possibility. He made them believe that they could be the next wave in Chicago politics, that they could build broad coalitions and move the city forward. What the president could or would not do for the country, they imagined carrying out themselves back home. As one staffer put it to me, “The idea of Obama is what we want. The actuality is more mainstream.”