The Friends of O
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Obama won his state senate seat, joining a Democratic minority in the body at the time, but soon grew bored with the slow pace of Springfield. He decided to challenge U.S. Rep. Bobby Rush in 2000. The reaction was cool. Minow recalls, "I know a lot of successful black businesspeople; I've done legal work for a lot of them. I called every single one I know, asked them for a contribution for Barack [against Rush]. I raised exactly zero dollars because they all said the same thing to me—quote, Let him wait his turn."
Toni Preckwinkle, the Fourth Ward alderman and longtime champion of the IVIs, backed Obama in the contest, in part as a turnabout because Rush had supported her opponents in the 1999 aldermanic elections. Preckwinkle is something of a Chicago archetype—the liberal reformer who is also a tough political infighter. She says she warned Obama that he was going to have a terrible time of it. "He got beat badly, partly because he wasn't a very good candidate, and partly because the weekend before the election, President Clinton did radio spots for Bobby."
Both Minow and Mikva argue that Obama was lucky to lose that congressional race. "He found out a lot about himself," says Mikva. "He just assumed that he had some natural affinity with black voters. [But] you earn votes. . . . The first time I heard him speak in a black church in that campaign, he sounded like a law professor."
The loss didn't temper Obama's ambition. One day in 2003, Minow recalls, Obama scheduled a lunch with Minow and announced that he wanted to be a U.S. senator. "I said, 'Are you nuts?' He said, 'No, I've thought it through.'" For months, the campaign looked like a long shot, at best. Minow says that later that same year, when he attended the public announcement of Obama's declaration of candidacy for the U.S. Senate, "there were, I think, only a few other white people there."
Stone recalls that not long after, he and Obama were "standing around the shrimp bowl" at a fundraiser for the Clinton Foundation. "I said, 'I don't get it: You lost to Rush, you've got a very strong field [of Senate candidates in the Democratic primary]; hang it up and become a full-time law professor and make something of yourself.' He said, 'I appreciate that but I really believe I have been given an opportunity.' I thought, 'What a waste.'"
Alan M. Dobry, a former Democratic committeeman of the Fifth Ward who had helped Obama knock Palmer off the ballot, observes that Obama brought an advantage to that 2004 race. He "has a lot of well-connected friends and some of them are quite affluent," Dobry says. "When he was a state senator, he used to be able to have benefits on the Near North Side, where he could go and raise a lot of money." At the same time, South Side black politicians, including state representatives Mary Flowers and Monique Davis, and the late Cook County Board president John H. Stroger, pointedly endorsed a white candidate, Daniel Hynes, now the state comptroller. Not incidentally, Hynes, son of the powerful political strategist Thomas Hynes, was backed by Mayor Daley's brothers John and Bill.
Upon winning the primary, Obama joined hands with the Daley organization to win the general election. Obama and Daley's alliances developed when Daley endorsed Obama for president and Obama endorsed Daley for mayor. Dobry says that maneuver alienated many IVIs. "I feel he essentially double-crossed us on the matter of being a liberal and went over to the Daley gang."
Will Burns, who has worked for Obama and for Obama's political godfather, Illinois senate president Emil Jones Jr., of the South Side, scoffs at the charge. "The Machine supported Paul Douglas for years and no one called him a sellout," Burns says. A Hyde Park intellectual and U.S. senator from 1949 to 1963, Douglas was one of the strongest liberal voices of the last century—and he was close to the former mayor Richard J. Daley.
Other sources say that Obama's error was not so much in embracing Richard M. Daley as in neglecting to go back to Hyde Park to explain his position and mend his fences. His detractors regard him as sometimes distant, even supercilious—a complaint that came up in the Bobby Rush race and that has resurfaced in the presidential campaign. "Barack tends to be somewhat aloof," Dobry says, "but that's been my experience with people from Harvard."
In any case, Obama's departure for Washington in 2004 opened a vacancy in his state senate seat. His successor would be named by the Democratic committeemen in the district. Obama told them that he wanted Will Burns in the job. In a stinging rebuke that attracted little public attention, the committeemen instead selected Kwame Raoul, who remains in the job. "Barack is not a committeeman," Burns says. "It was not his decision to make." Anyway, he says, "in politics and comedy, it's all about timing." Burns is now the Democratic nominee for a state representative's seat.
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The Obama campaign has long maintained that he decided to run for president in December 2006 during an annual vacation with his family in Hawaii. Actually, sources say, Obama's staff believed as early as the summer of 2006 that he would run in 2008.
Some of his early mentors, however, didn't know yet, and in September 2006 Obama spoke at the popular political steak fry hosted every year by Senator Tom Harkin of Iowa. The C-Span cameras stayed with Obama as he mingled with the crowd. "I watched it and saw a 21st-century Jack Kennedy," says Minow.
He and Mikva soon met with Obama to urge a White House run in 2008. "Ab and I both have three daughters and they all turned out very well," Minow remembers saying. "If you're going to run for president and be away from home a lot, you're better off doing it when your kids are small rather than when they are teenagers. That's when they really need a father." Obama's daughters, Malia and Sasha, were then eight and five years old.
Minow also told Obama, who at the time was 45, "Jack Kennedy told me when he was 39 he was going to run for president." (Kennedy made up his mind in 1956 after falling just short of winning the vice presidential nomination at the Democratic National Convention in Chicago.)
By the end of the year, Obama was calling Democratic operatives and fundraisers in Chicago, laying the groundwork of support for a run for the presidency.