By the time the Senate convened at 1:00 P.M. on Tuesday, Al Johnson and Tony Rezko’s entreaties had succeeded: in exchange for $30 million in what Miller called “black pork”—$6 million per year for five years for poor communities—Emil Jones backed the bill. Like Jones, three other African American Chicagoans—Rickey Hendon, Donne Trotter, and Jones’s sidekick Bill Shaw—switched their votes as well. After a brief, pro-forma debate, the bill passed 31–27, with Ed Petka and several other anti-gaming Republicans peeling off since their votes no longer were needed.
That night at the governor’s mansion, an end-of-session party brought out high spirits all around. The next morning Capitol Fax reiterated that 1999 was “The Year of the Rich White Guy.” With Illinois benefiting from what one lobbying firm’s session summary called a “red-hot economy,” the final budget as passed provided for $2 billion more in state spending than Governor Ryan had proposed three months earlier. The firm called the spring session “one of the most exciting and productive in recent legislative history,” but Barack firmly disagreed. “It’s very hard to separate yourself from the interests of the gaming industry if you’re receiving money,” he told National Public Radio in an interview excerpt broadcast the same day that Capitol Fax reported that Pate Philip had received $257,000 from gambling interests during the spring session and Emil Jones $86,000.
But Barack set off more fireworks on former Chicago alderman Cliff Kelley’s WGCI radio show when he told African American listeners that Springfield’s legislative black caucus “is not functioning as it should” because “we don’t have a unified agenda that’s enforced back in the community and is clearly articulated.” The next day’s Chicago Defender put Barack’s remarks on its front page under the headline “Obama: Illinois Black Caucus Is Broken.” Barack explained that “mistrust between the Black Caucus members in the House and the Black Caucus members in the Senate” dated back several years to disagreements about former governor Jim Edgar’s education funding proposal. He told another interviewer that the Wirtz and Crisp special-interest distributorship bills had highlighted the caucus’s disunity. “We were struggling to come up with a negotiating position the entire session,” he explained. “I don’t think we ever had a well-defined agenda, and so we were unable to leverage our votes at the end,” as Emil Jones had so successfully done on the hard-fought gaming bill. Black legislators “don’t need to be monolithic, but if we’re going to be effective, we’re going to have to have an agenda and unify around that agenda on at least some of these high profile issues where we potentially do have some leverage.”
Barack had expressed similar criticisms of his African American colleagues to fellow senator James Clayborne, but voicing such views on a premier radio program was taking it to another level. Barack “was somewhat impatient,” Clayborne remembered, “that we didn’t have the unification that we should have, that he wanted to unify us and move an agenda forward.” Clayborne had “told him ‘Unfortunately, if you jump out there too soon, you’ll turn people off. You’ve gradually got to work your way through the maze to try to get some unification and get us focused on an agenda.’”
When new young African American senator Kimberly Lightford joined the Black Caucus in January 1999, she quickly realized just how poisonous the closed-door dynamics were. Lightford had been surprised by what a cool reception her Democratic colleagues gave her, with southern Illinois veteran Vince Demuzio, Barack, and Miguel del Valle among the few senators who greeted the thirty-year-old warmly, often calling her “kiddo.” She knew that some senators saw her “as this little girl” and expected her to perform secretarial tasks, yet at the first Black Caucus meeting after her arrival, Barack nominated her as chairperson to succeed Donne Trotter. Kim quickly learned that the position was more difficult than she imagined because of Trotter and Hendon’s dislike for Barack. “We could barely have meetings in caucus because Donne and Rickey would give him hell.” Barack “wouldn’t argue with them,” he “would just leave. He avoided confrontation so well,” Kim recalled. “They felt he was arrogant” and believed he “had pretty much tricked Alice out of her seat.”
Hendon acknowledged that some meetings of both the Black Caucus and the larger Democratic one “got really heated,” with Barack sometimes agreeing with white senators like Denny Jacobs or Terry Link rather than with the Chicago African Americans. “There were some pretty raucous caucuses,” Bobby Molaro recalled, and George Shadid would specifically remember Rickey Hendon more than once telling Barack, “you ain’t black enough.” Hendon and Trotter’s personal behavior toward Barack remained just as problematic as it had been two years earlier. “I was so bothered by the both of them, and I was extremely bothered with Senator Hendon because he’s loud and he’s obnoxious,” Kim Lightford recalled. Barack’s public criticism of his black colleagues upped the ante, and “Donne more than Rickey took real offense at that,” well-connected lobbyist Larry Suffredin remembered. Everyone realized that Trotter was one of the Senate’s smartest members, but his sharp tongue was never at a loss for new, insulting put-downs based on Barack’s surname. By 1999 Donne was “always referring to him as ‘Senator Oh-My-Mama, trying to tell us all what to do,’” Suffredin recounted.67
By the end of the spring 1999 session, Barack’s disappointment with the Senate was manifest to almost everyone who knew him. “He just felt frustrated,” poker buddy Larry Walsh knew. “Springfield was not challenging enough for him.” Lobbyist and poker friend Dave Manning saw it similarly. “I think there was some frustration in having his family back home and having to come here all the time, often to accomplish very little” in a minority caucus that suffered under Pate Philip’s rule. The two House members with whom Barack had the most contact felt likewise. Barack “began to feel quite frustrated at the inability to make things happen,” Hyde Park’s Barbara Flynn Currie recalled. Tom Dart, whose largely white House district encompassed much of Chicago’s politically influential 19th Ward and who shared Barack’s policy interests, used the same adjective as all the others. “I remember him just being frustrated with the fact that so much of it was just personality driven” rather than policy focused. “I remember distinctly those conversations,” Dart explained. “Real frustration.”
Barack voiced similar feelings to friends who had nothing to do with Springfield. Miner Barnhill colleague John Belcaster would use the same word as Barack’s political friends. Barack felt “tremendous frustration” about “being in the minority party. . . . His frustration was palpable, and he would articulate it.” Miner Barnhill consultant and occasional golf partner Whit Soule would recall Barack grousing about being “a potted plant” in a system where the lobbyists “were drafting the legislation” and “the party leaders basically cut all the deals.” With Miner Barnhill’s Paul Strauss Barack “talked about how corrupt it was,” and writer friend Scott Turow would remember Barack calling and saying, “Man, I’ve got to get out of this place.” Ed Wojcicki of Illinois Issues listened to Barack vent and remembered him saying: “There’s really only five jobs I really want, now that I see what it’s like. I want to be attorney general, or I want to be U.S. senator; I want to be president of the Senate.” None of those were presently available, but to the Springfield denizens to whom he was closest, Barack had broached another possibility, one that Sun-Times political columnist Steve Neal had cited immediately after U.S. representative Bobby Rush’s loss in the mayoral primary in February: challenging Rush for his congressional seat in the March 2000 Democratic primary.
Barack shared this with Dan Shomon and with Will Burns, who had joined the Senate Democratic staff six months earlier. Burns recalled that “part of it was wanting to get out of Springfield” combined with “a sense that Bobby was vulnerable” because everyone knew Rush had run a “horrible” mayoral campaign. But Barack was also considering that Donne Trotter might challenge Rush. Burns knew “there was a little weird competitive thing between him and Donne,” one that had been building for two years now. Tr
otter was extremely well respected within the Senate, as much on the Republican side as on his own. Trotter’s excellent working relationship with Republican budget expert Steve Rauschenberger was recognized by everyone in the capitol. “We could work with Donne,” conservative Republican Ed Petka explained, and Trotter’s unquestioned status as the best-dressed man in Illinois politics, with a proclivity for colorful bow ties, drew admiration too. Petka saw Trotter as “an African American Paul Simon,” who also wore bow ties, and even Pate Philip saw Trotter as “a classy guy.” Donne “was a cooperative guy, and you could trust him,” Philip explained. “I always liked him.”
No matter how handsome and smart Trotter was, the cosmopolitan roots and academic pedigree of his eleven-years-younger junior colleague had led Donne to view Barack with an antipathy that would take years to finally dissolve. Trotter’s own undergraduate degree was from humble Chicago State University, and his disdain for everything the U of C represented manifested itself in his interactions with Barack’s young acolyte Will Burns, who had now earned two degrees there. Burns recalled, “The first time I met Donne Trotter, he called me . . . a fucked-up motherfucker” because of Burns’s ties to the U of C and to Barack. Trotter saw Rush’s mayoral run as a sign that “maybe he doesn’t want to be” in Congress, and in some quarters resentment still festered about how Rush had taken out Representative Charlie Hayes in the 1992 primary. Some of Trotter’s friends thought “Bobby was just not being effective,” and Trotter’s political godfather, powerful Cook County Board president John Stroger, “didn’t have any love for Bobby Rush, so I had that potential support behind me,” Donne recalled, especially because Stroger’s son Todd could then inherit Trotter’s Senate seat. Black lobbyist and former state representative Paul Williams remembered “there was a feeling that Bobby was vulnerable,” and Trotter believed that in a one-on-one matchup, all of the disenchantment with Rush could coalesce behind him. Trotter’s best friend Rickey Hendon had seen how “from the very beginning, Barack demonstrated ambition,” and with Barack now poised to deny Trotter a clean shot at Rush, Donne “clearly resented this new guy trying to jump over him.”
As Barack pondered a congressional run, in June he went to Santa Fe for the seventh Saguaro Seminar session and then back to Chicago for meetings of the Chicago Annenberg board and the legislature’s Joint Committee on Administrative Rules. Everyone involved in the Annenberg effort now understood that the four-year-old program was not producing dramatic improvements at most of the scores of schools it was assisting. As Northwestern professor Charles Payne told the board, “the moment CAC decided to work with and fund over 220 mostly lower tier schools, we knew there was not going to be a deep impact,” in large part because data showed that recipient schools were getting an average of only $49,000, hardly 1 percent of most schools’ annual budgets. The board agreed to adopt a “Breakthrough Schools” initiative whereby most of CAC’s remaining funds would be concentrated on eighteen particularly strong schools.
At the end of June, Barack flew to New York for the first true board meeting of the incipient think tank that was now calling itself the Network for American Renewal. The advance concept paper envisioned programs addressing “Shared Prosperity and Human Well-Being” and “Renewing American Democracy for the 21st Century.” Cofounders Charles Halpern and Stephen Heintz imagined this first gathering as “potentially an historic occasion,” and Barack’s fellow board members included former Colorado congressman David Skaggs and Public Allies cofounder Vanessa Kirsch. Barack told his colleagues that “part of the opportunity and challenge is to develop norms and values that unify us as Americans but are also inclusive of the norms and values brought by other cultures.” He also “stressed that while the Network does not plan to focus on issues of race and culture with specific projects, we must address these issues in all our activities” and must also consider “how we include people who are not sharing in prosperity,” because “whatever ails this country ails poor folks worse.” One proposed project would focus on “Asset Building,” such as “inner-city entrepreneurship.” Barack noted that the “concept of ‘ownership’ is an extremely powerful American notion,” and he “expressed special interest in the notion of community assets,” again echoing John McKnight.
Another anticipated focus was “Democracy and Devolution,” with Barack citing his own past experience in noting how “‘motor voter’ registration is not really at all significant. The problem is not voter registration but voter participation. How do you engage citizens in their government?” He complained about how in Illinois “hundreds of millions of dollars in tax breaks were approved without knowing what impacts they will have,” and no matter what the group might initiate by way of “devolution” at the state level to anticipate “resistance on the part of legislators who like things the way they are.” A key question was “Where do citizens collectively assert their rights and interests,” which “is central to the current state of democracy”?68
Back in Chicago, on July 1 Barack made his first move toward a congressional race by agreeing to Dan Shomon’s idea of conducting a small, discreet poll of 1st District voters to explore just how vulnerable Bobby Rush might be. Dan asked his three closest Springfield friends, Senate Democratic staffers John Charles and Adelmo Marchiori and former staffer Jeff Stauter, for their confidential help, explaining that “Barack is thinking about doing this.” Adelmo knew that “the relationship between Barack and Shomon was the tightest on staff,” and although they thought Barack “was going somewhere, we still questioned Shomon’s bromance with Obama,” Jeff recalled. “I had the software to do the poll,” John explained, “some statistical sampling software that I’d picked up along the way” while polling for state Senate campaigns. Shomon bought “a list of phone numbers from a vendor” there in Springfield for $450, and “we put together this poll,” Adelmo remembered. “We were completely on our own personal time,” making sure no word of their project seeped back to chief of staff Courtney Nottage. Working out of Stauter’s lobbyist office, they “spent night after night calling” residents of the 1st Congressional District, which ran from 26th Street down to 103rd Street on Chicago’s South Side, then westward through Englewood to encompass predominantly white Beverly and parts of suburban Evergreen Park, Oak Lawn, Alsip, and Blue Island. “You test your opponent’s negatives,” and “we would have done a favorability of Barack and Rush,” they remembered. Overall they completed about three hundred calls, four young white men asking respondents who were more than 75 percent African American to voice their feelings about former Black Panther leader Rush. The bottom-line question was “Is it doable? Is it worth taking the shot?” and John Charles recalled that after a week’s worth of phone calls, “our numbers showed that it was possible.”
Barack was encouraged by the amateur poll, but the tallest barrier to launching a challenge was right at home: Michelle. “With every political run that Barack made, my instinct was to talk him out of it,” she later recounted. Malia was just celebrating her first birthday, and with Barack in Springfield for so much of the spring, and then out so many evenings at political events like a “Second Thursday” DL21C speaking appearance, Michelle “was in a lot of ways a single mom, and that was not her plan,” her close friend Susan Sher explained. This campaign would be far more demanding than either of Barack’s state Senate wins, making an already bad situation far worse, no matter what the outcome, and Michelle told Barack she was opposed to it.
As Barack surveyed his closest political friends, he heard far more opposition than support. Carol Harwell declined to be involved, and Terry Link and Denny Jacobs each said such a challenge would be “foolish” and “stupid.” So did Mike Lieteau. “I told him he shouldn’t run,” Mike said, and warned Barack that even he would support Rush. “Bobby was a personal friend of mine” and “was very supportive of me personally and very supportive of telecom issues, so I had no choice.” Politically savvy lawyers John Schmidt, Matt Piers, and Newton Minow said th
e same. “I thought it was a terrible idea,” Schmidt recalled, and Piers remembers, “I thought it was crazy.” Minow was even blunter: “Are you nuts? Barack, I think this is a mistake.” African American acquaintances responded similarly. Sokoni Karanja had long thought Barack eventually would run for mayor but felt this was “a bad move. I said, ‘Barack, what are you doing? You can’t beat Bobby’” and “‘folks are going to react badly’” to him trying. Lobbyist and former state representative Paul Williams told Barack, “you aren’t the guy for the blackest district in the country,” and former Harold Washington aide Tim Wright, who had been Rush’s chief of staff before a recent falling-out, advised Barack that “This isn’t the race, this isn’t the time.” When Barack asked 6th Ward alderman Freddrenna Lyle to lunch and revealed his plan, “I explained that I thought the seniors in my area remembered Bobby when he was with the Panthers, and they had a connection to Bobby that I thought was unbeatable,” irrespective of how poor a mayoral race Rush had run or how good a state legislator Barack was.
Barack was encouraged by a Chicago Tribune Sunday magazine story in which well-known black businessman Dempsey J. Travis, once a top supporter of Harold Washington, said that Barack and Jesse Jackson Jr. were Washington’s successors: “there are people we have coming up who have shown they have the class, the intellect and the people skills to do exactly what Harold did—strong people who are bright, sophisticated, sharp. Razor sharp,” Travis stressed. “Harold lives on in these people.” Barack also took pleasure from a Hyde Park Herald interview with him headlined “Hyde Park’s Own Renaissance Man.” He made no mention of the congressional possibility but cited three top local challenges: “the continuing under-performance of the public schools,” whether residents feel “confident that they can raise and educate their children here in safety,” and how to “foster economic development and economic integration . . . to include the larger South Side,” because Hyde Park was in danger of becoming “an island of prosperity within a sea of poverty.”
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