by David Garrow
As Barack continued his private conversations about a congressional run, he did receive some positive feedback. State representative Tom Dart, whose district was part of Rush’s, encouraged Barack to run. So did both 4th Ward alderman Toni Preckwinkle, whom Rush had opposed when she defeated two primary challengers back in February, and, more surprisingly, new 5th Ward alderman Leslie Hairston. Barack had not supported Hairston when she took on incumbent Barbara Holt, and Hairston also knew how other Side South politicians disliked Barack because of the perception that “you think you’re better than us.” A $2,000 contribution from Barack’s campaign account to Hairston’s was a thank-you for her support.
A trio of independent-minded young black professionals also responded positively. Thirty-two-year-old Tim King was a South Side native and Georgetown University law graduate who in 1995 had become president of a struggling Roman Catholic high school, Hales Franciscan, after finding teaching far more fulfilling than the law. King’s work at Hales won rave reviews, with a laudatory Chicago Reader profile detailing his unceasing commitment and a Chicago Tribune editorial praising him for taking in an orphaned sixteen-year-old who then graduated from Hales and headed to college. Barack had visited Hales to introduce himself, and the two had “hit it off” and would see each other at the East Bank Club and in Hyde Park. When Barack told Tim, “I’m thinking about running for Congress,” Tim echoed the thought: “Really? I’m thinking about running for Congress!” Barack “looked at me very seriously” and said, “If we both run, there’s no chance either one of us will be able to win.” Tim concurred: “You’re absolutely right, and I defer to you.”
Tim agreed to be an active supporter, as did Barack’s friend Jim Reynolds, whose thriving Loop Capital firm now employed Barack’s brother-in-law Craig Robinson. “Jim, I’m thinking about running for Congress,” Barack remarked one summer day while they played golf, and Reynolds eagerly signed on. So did a brand-new acquaintance, Judy Byrd, another Georgetown University law graduate who had met Barack years earlier while working in Chicago city government under Howard Stanback. Like Reynolds, Byrd’s friends included a number of well-heeled Chicagoans, and she offered to set up a lunch to introduce Barack to four or five friends who were “all women of some means.”
Neither Barack nor Donne Trotter told the other about their plans, but each one spoke privately to Emil Jones, who remembered that Barack “told me that he might run for Congress, so I said, ‘I think you’d be good, go ahead and run.’ I said, ‘You are aware that Donne Trotter’s running as well, and that being the case, I cannot be involved . . . I cannot choose between my membership.’” Trotter had the same conversation with Jones. “Emil in my mind was neutral,” Donne explained. “His whole thing is he didn’t want us using his staff to fight,” as Barack already surreptitiously was, and word went out from Jones that no staffers could take leave to work on either campaign: any departure would be permanent.
Thanks to his lobbyist friend Vince Williams, who knew firsthand that “the mayor was very interested in getting to know Barack,” Obama also called on Richard Daley, who had badly thrashed Rush just five months earlier. Daley seemed friendly and receptive, reinforcing Barack’s assumption that Daley would quietly welcome a challenge to someone who had challenged him. Barack mentioned his meeting with Daley to Madeline Talbott, who along with new 15th Ward alderman Ted Thomas was more than willing to have ACORN back Barack. “Both Barack and I felt like Bobby was very vulnerable,” Madeline recalled, even though “no one knew who Barack was.” Barack also mentioned his meeting with Daley to former judge and House member Ab Mikva, who believed “Rush was no great shakes as a congressman” and encouraged Barack to challenge him. But Mikva also tried to dissuade Barack from misunderstanding Daley’s stance. Barack “thought that he would get Mayor Daley’s support,” telling Mikva that “at the end . . . the mayor stood up and said, ‘Well, good luck to you.’ And Barack said, ‘Well, I read that that maybe he’s open.’ And I said, ‘No, it’s closed, because that’s what the old man’—Daley’s father—‘used to say, “Good luck to you, fella,” and that meant that you were on your own.’”
Barack had a similar exchange with John Kelly, a young white Irish lobbyist to whom Emil Jones had taken a liking and who had important family connections in Chicago politics through his uncle, powerful Cook County assessor Jim Houlihan. Kelly was just getting immersed in the world of Springfield, and although Barack “seemed very politically calculating,” he was not “a mainstream player in Springfield . . . because he wouldn’t go out at night.” Kelly thought the congressional race “was a natural progression for him” when Barack mentioned it, asking for his support. But during a summer golf outing at Ravisloe Country Club, in south suburban Homewood, Barack told Kelly that “The key thing is where the mayor’s going to be.” Kelly replied, “‘It’s very clear where the mayor’s going to be: the mayor’s going to be with Bobby Rush.’ And he said, ‘Why are you so hell-bent on the fact that he’s going to support Bobby Rush?’ I said, ‘’Cause it’s kind of Politics 101, Barack. He beat Bobby Rush, and he knows that he can beat him again, and he’d rather have him there than you there.’ He said ‘Why?’ And I go, ‘Because he doesn’t know if he can beat you. Bobby Rush is a known quantity: they know that they can beat him. They don’t know where you’re going to end up.’” Barack “looked at me kind of like it was shocking to him,” and Kelly realized that Barack’s “huge” political naiveté stemmed from him not being from Chicago.
Chuy Garcia, a 1998 machine victim, said that Daley “had seen Bobby’s full potential in the challenge against him,” and “didn’t see him as a larger threat.” But Daley “saw a lot more crossover potential” with Barack, whose “credentials were pretty impressive, so the potential for trouble was much bigger.” As Kelly had told Barack, it indeed was Politics 101: “Why should a sitting mayor help someone who can eclipse him down the road: in debate, in credentials, in being an alternative to the mayor?”69
One benefit of the huge Illinois FIRST appropriations that Barack had reluctantly backed was the ability it gave senators to direct sizable grants of state funds to quietly chosen recipients, and over the summer, Barack completed the paperwork to channel $462,000 to seven fortunate organizations. He directed almost half of that, a whopping $200,000, to the Citizenship Education Fund’s LaSalle Street Project, to assist in “setting up [a] venture capital business for underserved areas.” The fund, a nonprofit arm of Rev. Jesse Jackson Sr.’s Rainbow/PUSH, had initiated the project a year earlier as a spinoff of its two-year-old Wall Street Project, which was aimed at drawing investment dollars to poor neighborhoods. Taking its name from Chicago’s premier banking street, it was supported by Jim Reynolds as well as the Chicago Urban League. Crain’s Chicago Business labeled the project “far more of a publicity tool than a power broker” in a story highlighting how local heavyweights were backing the highly similar Social Investment Forum of Chicago. Karin Stanford, the fund’s executive director, had just resigned and given birth to a child, and two years later the LaSalle Street Project would be shuttered after news that Jackson Sr. had fathered Stanford’s daughter.
Barack also funneled $100,000 to the South Side YMCA for construction of a child development center and $50,000 apiece to two youth service programs for teen mentoring efforts. A trio of smaller grants, including one for a senior day care van and $20,000 for South Shore’s Black United Fund, rounded out Barack’s summer gift list. In mid-July the weekly Hyde Park Herald reported that both Donne Trotter and Barack were considering challenges to Rush. Trotter said “nothing is definite” but he was “leaning in that direction.” Local activist Alan Dobry stated that “the congressman is vulnerable,” and Trotter said that “my question is what has he done. I think he’s a great individual, but if your friends aren’t doing the job you expect them to, you don’t just leave them there.” Barack told the Herald, “I haven’t made a decision yet” although “it will need to be fairly soon.”
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bsp; By July 25 Barack finally had Michelle’s reluctant acquiescence, and he began contacting his oldest and closest friends, asking them to make the maximum $1,000-per-person contribution. Hasan Chandoo immediately wrote a check, as did Gerry Alexis, Rob Fisher, Jeff Cummings, Jean Rudd, Bettylu Saltzman, and Michelle’s friend Cindy Moelis. Barack already had $1,000 apiece from Judd Miner and his young friend Robert Blackwell, and before the end of July, Debbie Leff, Douglas Baird, and Newton Minow gave as well. On July 28 Barack mailed both an official “Statement of Candidacy” and a “Statement of Organization” for Obama for Congress 2000 to the Federal Election Commission. Jean Rudd’s husband Lionel Bolin was again listed as the campaign’s official treasurer, with Barack and Michelle’s friend Craig Huffman joining sister-in-law Janis Robinson as two assistant treasurers. Cynthia Miller had just returned to Chicago from abroad, and she plus Al Kindle, 4th Ward alderman Toni Preckwinkle’s top political worker, and Amy Szarek, a young fund-raiser who had worked on Carol Moseley Braun’s unsuccessful 1998 race, started pulling things together as Dan Shomon and Will Burns, Barack’s two most dedicated aides, began planning to leave Senate staff to take charge of the incipient campaign.
On August 1 the Chicago Tribune and the Chicago Sun-Times caught up to the Herald’s report from two weeks earlier. Barack said he was “seriously considering” a race and expected “to make a final decision” in “the next couple of weeks.” Four days later the Defender followed up, with Barack saying he had been discussing “a possible candidacy” for “the last two months” and would continue “seriously considering” a run “for the next several weeks.” Both Toni Preckwinkle and local state representative Barbara Flynn Currie felt strongly that Barack needed to get started as soon as possible if he was going to challenge a well-known incumbent, but ten days into August Barack told the Herald, “I will be making a decision before Labor Day.” He explained that “it’s important for me to discuss the possibility of my candidacy with a wide range of community leaders” and “that process has not yet been completed.” The next day he told the Sun-Times’ Lynn Sweet that “at this point, it looks like we are going to go ahead with this,” and Donne Trotter told her that he too was “more than likely” to run.
That same day, August 11, the campaign rented the first of two offices, on 87th Street near Cottage Grove Avenue, arranged phone service, and issued its first payroll checks to Will Burns and Amy Szarek. On Saturday Al Kindle took Barack to march in black Bronzeville’s biggest annual event, the Defender-sponsored Bud Billiken Day parade, which featured marching band and drill team competitions as well as a full array of South Side politicians. “No one knew who he was,” Kindle recounted. “People were asking ‘Who is he?’” and Barack “seemed a little embarrassed,” Kindle remembered. “You could see how humbling it was in his face.” Capitol Hill’s Roll Call included Bobby Rush in a story on endangered incumbents, saying Rush “has been viewed as vulnerable to a Democratic threat” since his mayoral thrashing, but the Sun-Times’ Steve Neal warned that Rush “has a solid base of about 40 percent of the vote.” Neal predicted that Barack could outpace Rush in fund-raising, collecting at least $500,000 for the race, and the mayoral disaster had shown that Rush’s organization “is relatively weak.” Donne Trotter “will attempt to portray Obama as a newcomer to the South Side,” and a black weekly warned that Barack “is likely to get some unwanted opposition from friends of former state Sen. Alice Palmer,” who “has not forgiven Obama.”
Neal believed that “Trotter and Obama are genuine threats” to Rush, but former senator Paul Simon was far more cautioning when he had breakfast with Barack one mid-August morning. Simon emphasized that Barack must win public endorsements from prominent African Americans in order to credibly challenge Rush, but Barack had already been told by senior figures like former attorney general Roland Burris that they would not support him. “My instinct is that you will be portrayed as ‘the white man’s candidate’ for this seat,” Simon warned in a prescient thank-you letter, “virtually portraying you as an Uncle Tom.”70
Barack turned his attention toward another round of fund-raising calls, with $1,000 checks coming in from his uncle Charles Payne, Davis Miner colleague Paul Strauss, Sidley & Austin’s Eden Martin, Jim Reynolds and his wife Sandra, John Rogers Jr., Pat Graham, and Tony Rezko and his wife Rita. A second and larger campaign office was secured just south of 95th Street on Western Avenue, and by the end of August Cynthia Miller was on the payroll, soon to be followed by campaign manager Dan Shomon. In the world of Springfield, it “was a big deal” when Shomon and Will Burns gave up their Democratic caucus jobs to sign on with Barack, with some colleagues such as Cindy Huebner wondering “why in the hell is Barack doing this?” Paul Simon’s sidekick Mike Lawrence reacted similarly when Barack checked in with him by phone. “Why are you doing that?” Mike asked. “I don’t think it’s a good idea. I think your future is statewide,” not South Side.
Eager for press attention, Barack capitalized on a big mid-August power failure to propose toughening a state law that failed to require utilities to reimburse customers for damages unless an outage lasted more than four hours and losses totaled at least $30,000. Barack devoted a Hyde Park Herald column, a Chicago Tribune op-ed, and a letter to the editor of the Chicago Defender to the problem, his biggest outreach effort to date. He, Shomon, and deputy campaign manager Will Burns began recruiting friends and acquaintances like young organizer John Eason and Democratic activist John Corrigan to devote time to the campaign. Like Will, his good friend Eason thought the race was actually about more than a congressional seat. “You just wanted this guy to go as far as he could, and you wanted to do whatever you could to get him to go as far as he could, and ultimately I think what we’re all thinking is ‘Oh, we can get another Harold Washington. We’ll get him in as mayor,’ and even he talked about that.” Of course “nobody would say anything publicly against Daley,” but “it was the same trajectory as Harold: you run for Congress and you get attention on the national stage and that’s just so you can run for mayor. . . . You want to be mayor of Chicago,” and Barack “knows that’s what I want to hear.” But underlying everything, Eason realized, was Barack’s intense aversion to Springfield. “I remember him saying he needed to get out of Springfield desperately—he desperately needed to leave Springfield.”
Barack also drew public attention, even on the Defender’s front page, by decrying how Governor Ryan in mid-August had vetoed his bill mandating that at least two-thirds of child support payments actually go to the children. “One of my biggest concerns in the legislature has been helping people move out of poverty,” and HB 1232 was “a pretty common sense” effort in that direction. Barack vowed to seek an override come mid-November’s veto session, but a Saturday town hall meeting at a Baptist church in Englewood attracted just twenty people. Barack called for a moratorium on capital punishment and tried to educate the tiny crowd by pointing out how “some of the biggest contributors to Governor Ryan’s” and even “Emil Jones’s campaigns are gaming interests.”
Barack devoted much of mid-September to another burst of fund-raising calls, with $1,000 checks coming in from his brother-in-law Craig Robinson’s good friend Marty Nesbitt as well as Nesbitt’s boss, wealthy real estate heir Penny Pritzker, John Rogers’s Ariel colleague Mellody Hobson, basketball buddy Eric Whitaker, law firm colleagues George Galland and Chuck Barnhill, real estate manager William Moorehead, and Harvard Law School professors Martha Minow, Larry Tribe, and Randall Kennedy as well as new supporter Judy Byrd. Barack prepared to step down as chairman of the Chicago Annenberg board, and in midsummer Howard Stanback had already succeeded him as chairman of the Woods Fund’s board, while at the same time Bill Ayers joined the board. On Tuesday, September 21, the campaign reserved a Palmer House ballroom in the downtown Loop for a Sunday-afternoon announcement ceremony five days later, and the next morning Steve Neal reported that Rush was gearing up for a reelection campaign. Former representative Gus Savage’s
longtime chief of staff, Louanner Peters, would manage it, and while Citizens for Rush had only $94,000 in the bank, Rush had just put his wife Carolyn on its payroll. Rush had met Barack briefly seven years earlier during Project VOTE! and remembered him as “a very persuasive young man” with “a sunny disposition” and “a certain charisma about him.” That September, reaching out first to political science Ph.D. and Citizen Action veteran Don Wiener and then to political consultant Eric Adelstein, Rush wanted Wiener to research Obama’s record. “I don’t know much about him. He seems like kind of an Oreo to me.”
As of August, Barack believed he had veteran political strategist David Axelrod and his longtime partner John Kupper lined up to be his primary media consultants, but that quickly came unglued. “We actually started doing the race,” Kupper recalled, and had “started advising him,” but then “we started getting calls saying ‘You cannot work against Bobby Rush. If you do, you’ll never work for another Democrat again,’” Kupper recounted. “There was pressure from the DNC [Democratic National Committee] and from Washington that caused us to get out of the race,” and a direct-mail firm, Crounse Malchow, likewise backed away from Barack. Other well-known Chicagoland consultants like Pete Giangreco and Delmarie Cobb cited their past ties to Rush in declining to get involved, and Axelrod told Dan Shomon to call Chris Sautter, his D.C.-based former partner. Sautter flew to Chicago to have breakfast with Barack and Dan and accepted the handoff from Axelrod and Kupper.