The Friends of O

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Inside the circle of Chicagoans who spotted Barack Obama's talent, helped guide his path—and made it hard for him to close the deal (even before the Reverend Wright eruptions)

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When Barack Obama ran in the Democratic primary for a South Side congressional seat in 2000, one of his opponents, Donne Trotter, raised a curious accusation. "You just have to look at his supporters," Trotter told the Chicago Reader that year. "Who pushed him to get where he is so fast? It's these individuals in Hyde Park, who don't always have the best interests of the community in mind." The Reader also mentioned rumors that Obama was a creature of a cabal of white Hyde Park liberals—a group that created something called the Obama Project to groom the young Harvard-trained lawyer for high office.

If Trotter or anyone else was trying to plant the notion that Obama was only a figurehead or a mouthpiece for some self-serving liberal elites, the conspiracy charge did not seem to have a decisive impact. In the end, the incumbent congressman, Bobby Rush, won easily, with Trotter getting only 7 percent of the vote and Obama around 30 percent. Even so, as Obama has gone on to stunning electoral success since then, he has not entirely escaped echoes of the Obama Project accusation.

More than a score of people interviewed by Chicago who were close to Obama in the 1990s dismiss the idea that some kind of secretive group schemed to produce the man who is now a leading candidate to win the Democratic nomination for president. Indeed, several people who tried to recruit Obama when he got out of Harvard Law School in 1991 say that he returned to Chicago with a political career in mind—in other words, he was his own Obama Project.

Still, Trotter's premise touches some threads of truth. (Trotter, who has endorsed Obama for president, did not respond to requests for comment.) Obama made his home in Hyde Park, and the liberal, diverse South Side neighborhood serves in some ways as a metaphor for the man. On the one hand, Hyde Park has been the historical incubator of reform politics in Chicago. Early on, Obama found friends and powerful patrons there—some white, some black—with similar beliefs and the ability to boost his career. On the other hand, Hyde Park is the home of the University of Chicago, known as a center of conservative thought, where Obama taught in the law school and socialized. Though his policies clearly tilt toward those of the Hyde Park liberals, Obama supporters find strains of the U. of C. in his thinking, notably in an openness to free-market solutions.

Hyde Park piles on baggage, too. Obama continues to face sniping that he is an elitist, a loose and loaded term that nonetheless reflects a stereotype of that intellectually charged university neighborhood—and exactly the sort of charge that has made it hard for him to "close the deal," in the parlance of the presidential campaign. What's more, Obama has made enemies there as he has moved up the political ladder, and he has disappointed some old allies, particularly reformers, dismayed that he's a friend of the Daley administration (for more on Obama's relationship with Mayor Daley, see "Making Peace"). Indeed, with a few exceptions, Hyde Park has long been marginalized in Chicago politics; the idea that the neighborhood might produce the country's president is little short of remarkable.

Nonetheless, Hyde Park, seven miles southeast of the Loop, proved a warm and nurturing base for the ambitious young lawyer. The Obama Project may be a figment of someone's imagination, but it's clear that in Hyde Park and in similar liberal enclaves around Chicago, a great many people recognized Obama's talent and boosted his progress, believing fervently in his promise. "When I first met Barack, I believed he could be president," says Valerie B. Jarrett, a close friend since 1991, a former city official, and now an adviser to his campaign.

Barack Obama first came to Chicago in 1985, taking a job as a community organizer shortly after graduating from Columbia University in New York. He spent three years working for the Developing Communities Project in Roseland and West Pullman, but he grew frustrated at what he could accomplish and decided to become a lawyer, enrolling at Harvard. While still there, he started attracting significant Chicago mentors. None have been more important than Abner Mikva, a powerful figure in Chicago and national Democratic Party politics for 40 years. He has served as a congressman both from Hyde Park and the North Shore, as a federal judge, and as White House counsel to President Bill Clinton. In 1990, sitting on the U.S. court of appeals in Washington, D.C., Mikva heard from his law clerk that a young man had just been elected the first African American president of the Harvard Law Review. "I was always looking for diversity among my clerks," Mikva says, so he tried to interview Obama for a clerkship, a coveted position, especially on that prestigious court. Obama turned him down. "I said jokingly, 'Oh, he's one of those uppity blacks who will only work for black judges,'" Mikva recalls. Mikva's clerk said no—Obama was headed back to Chicago to run for public office.

The previous year, Obama had been hired by the firm of Newton Minow, Mikva's childhood friend and fellow Democratic insider. Assistant counsel to Illinois governor Adlai Stevenson and chairman of the FCC under President John F. Kennedy, Minow is senior counsel at the gold-plated Loop law firm now known as Sidley Austin. His daughter Martha taught Obama at Harvard Law. Obama came to Sidley Austin as a summer intern in 1989. Later the firm offered him a second internship, which would likely have been followed by a permanent job. "He said, 'I can't take the job,'" Minow recalls. "I said, 'Why?' He said, 'I'm going to go into some form of politics.'"

Obama had some other news for Minow as well. Michelle Robinson, a Sidley Austin attorney, had been assigned that first summer as Obama's mentor. "He said, 'I'd rather you sit down when I tell you this. . . . I'm taking Michelle with me.' I said, 'You no-good, worthless, rotten . . .' He said, 'Hold it: We're going to get married.' I said, 'That's different.'" Minow and his wife, Jo, remain friends with the Obamas, the couples sometimes attending concerts at Ravinia together.

Barack and Michelle were married in 1992 by the Reverend Jeremiah A. Wright Jr. at Trinity United Church of Christ, 40 blocks south of Hyde Park in Washington Heights; Obama joined the church later that year. Snippets of Wright's percussive sermons and subsequent public statements have caused roiling trouble for Obama's presidential campaign, prompting the candidate to denounce his former pastor and deemphasize Wright's influence on his thinking. But, according to Obama, a 2007 book by the Chicago Tribune reporter David Mendell, Obama sometimes used Wright as a sounding board for his political aspirations. The pastor himself has traveled in political circles—for example, he advised Harold Washington. Back in Hyde Park, the newly  wed Obamas bought a condo at 5450 South East View Park near Lake Shore Drive and Jackson Park. Barack liked to play pickup basketball games on nearby courts.

Michelle brought her own powerful neighborhood connections to the marriage. She grew up in South Shore, the nearby working-class enclave to the southeast of Hyde Park, with her close friend Santita Jackson, daughter of the Reverend Jesse Jackson. Michelle went to Princeton University, where her brother, Craig Robinson, played basketball with Hyde Parker John W. Rogers Jr.

Rogers exemplifies a dimension of Hyde Park often overlooked in accounts of Obama's career—young African American entrepreneurs. Rogers founded the nation's first African American money-management and mutual fund, Ariel Capital Management, and he is chairman emeritus of the Alliance of Business Leaders and Entrepreneurs (ABLE), a group of black CEOs of Obama's generation. Rogers's former wife, Desiree Rogers, a longtime friend of Michelle Obama, is president of Peoples Gas. Valerie B. Jarrett, one of the closest advisers to both Obamas, is CEO of the residential real-estate giant The Habitat Company. John Rogers, Jarrett, and Allison S. Davis, a lawyer and developer,  all grew up near a stretch of South Greenwood Avenue. Obama's close pal Martin Nesbitt, former chair of the Chicago Housing Authority, is president of PRG Parking Management. These and other figures have been crucial Obama supporters and, in many cases, fundraisers. "Many of us were able to introduce [Obama] in our workplaces," says Alan S. King, a lawyer who studied for the bar exam with Michelle. "That expanded his base of support, raised his profile, and enhanced his fundraising efforts."

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