And yet, in Washington, Jackson never quite mastered the rhythms of Capitol Hill. A Tae Kwon Do devotee, he’d sometimes be spotted walking through the marble halls of Congress in his dobok, and he seldom lingered on the floor to schmooze. His colleagues viewed him as something of an oddball and a loner. (People on the Hill say that it’s telling that the only congressman to visit Jackson at the Mayo Clinic has been Dennis Kucinich.) “He was not a guy who seemed to warm to the artificial camaraderie of the House,” Davis says. Although Jackson frequently claimed that he hoped to be the first black speaker of the House, his heart never seemed in the pursuit. “People who talk about wanting to be in leadership are rarely successful at it and he never really worked to cultivate those relationships with members,” a senior Democratic House aide says. “He was good at the presentation of politics, but the actual behind-the-scenes execution was always a little clumsy.”
Instead, Jackson’s focus was back in Chicago, where he was building a formidable political machine. In the basement of his house, a block from Lake Michigan, Junior constructed a campaign war room. He filled it with computers, phones, even a giant mail machine capable of producing thousands of four-color mailers—and he would take candidates there to show them the political muscle he could provide if they earned his support. “He was meticulous in his preparation,” recalls Alexi Giannoulias, who sought and received Jackson’s endorsement for his 2006 state treasurer’s campaign. “When I met with other people, I’d say, ‘Here’s why I want to run.’ I’d give them my heartfelt pitch about why I wanted to be in public office. With Junior, he’d say, ‘I want to hear your pitch, but I also want to see polling, how much money you’re going to raise, who’s running your campaign. Give me the numbers and the names.’ ”
Jackson began to assemble what some around him called a “farm team.” He seeded the Chicago City Council, local county commissions, the Illinois State Legislature, and state executive offices with his allies. At one point, he helped his minister get elected to the State Senate; a few years later, he spearheaded his wife Sandi’s successful campaign for Chicago alderwoman. Meanwhile, Jackson worked to build up his fund-raising base. Some traditional Democratic patrons, including Jewish Democrats, were off-limits. “He doesn’t have a great calling card with North Shore lakefront liberals because they’re very suspicious of the Jackson family,” one prominent Illinois Democrat explains. So Jackson created new donor groups, cultivating relationships, for instance, with members of Chicago’s growing and increasingly wealthy Indian community, including Raghu Nayak.
And then there was his signature issue: the construction of a third airport in the cornfields 40 miles south of Chicago. Junior argued the airport would be an economic-development engine for the whole South Side. But it would be a political engine for him, too. For years, O’Hare, which is run by the City of Chicago, had been a major patronage operation for Mayor Richard Daley and other Chicago politicians. The new suburban airport would be managed by a commission that was dominated with Jesse Jr.’s supporters, giving Jackson his own patronage candy bowl. No one in Chicago was entirely sure what Jesse Jr. intended to do with the political machine he was building, but one thing was clear, says a prominent Illinois Democrat: “It was designed for something bigger than getting reelected to represent the Second District every two years.”
A U.S. Senate seat was bigger, and Jackson began eyeing the one held by an unpopular Republican who would be up for reelection in 2004. “That seat had Junior’s name on it,” says Hermene Hartman, a longtime Jackson family friend. Then, in the fall of 1999, a riot broke out at a high-school football game in Decatur, Illinois, leading to the expulsion of several black students. The Reverend Jackson protested their expulsions—comparing Decatur to Selma and saying the students were victims of racism—and eventually went to jail for his efforts. A video subsequently emerged showing the students had indeed incited the riot. The Reverend Jackson looked like a fool. “Jesse Jr. said, ‘There’s no possibility that I could win the election,’ ” Frank Watkins, Jesse Jr.’s longtime press secretary, recalls. “ ‘My dad was recently in jail in Decatur, and I’m going to go down there and ask for their vote?’ ”
A young state senator named Barack Obama did not have that sort of baggage, and in 2002, he met Jesse Jr. at a Chicago restaurant. Michelle Obama had been a Jackson-family friend for years, having gone to high school with Jackson’s older sister, Santita, and Jesse Jr. (who once confessed to having a boyhood crush on Michelle) had attended the Obamas’ wedding. Over breakfast, Obama told Jackson that if he planned to run for the Senate seat, Obama wouldn’t, but if Jackson wasn’t running, could Obama have his support? Jackson gave it to him, putting his basement war room at Obama’s disposal and appearing on billboards and mailers with him. For Obama, who had lost a congressional race in 2000 over doubts about whether he was “black enough,” Jackson’s backing was crucial.