by David Garrow
Like Jean Rudd, Ken Rolling had gotten to know Barack well during those early years, but the five years that they worked together were “a time of his life that was I think stressful,” Ken recalled. “Money was always a big issue” because “they were in debt” and “living on the edge.” More than once Barack vented to Ken. “She’s on me. Michelle wants money. ‘Why don’t you go out and get a good job? You’re a lawyer—you can make all the money we need.’” One night Barack got “really upset” when Ken called to say he needed the board chair’s input on a pending decision. “God damn it, I’m not getting paid for this. I can’t spend my time on this,” Barack yelled into the phone. “‘Thank you’ was very hard to come by,” Ken recalled, and after the congressional loss, Ken too heard Barack profess doubt. “I don’t know. I think I might just chuck this whole thing, and I’m just going to go get myself a good job and make some money.”27
Jesse Ruiz heard similar comments at a summer breakfast. Barack “was very demoralized” and was “complaining about Springfield,” Ruiz recalled. “A lot of my classmates are partners at law firms now,” Barack said, adding that “you probably earn more than I do!” In midsummer Barack, Michelle, and two-year-old Malia traveled to Washington to see Rob and Lisa Fisher. The visit began inauspiciously, with Barack telling their hosts, “‘We’ve forgotten our suitcase,’ and Michelle was like, ‘We didn’t forget our suitcase! I packed for me and Malia, you forgot your suitcase!’” Rob and Lisa already knew “there’s no question as to who’s the boss of that household,” and it was readily apparent how unhappy Michelle was with Barack’s political life. “Michelle’s pushing him hard at that point,” Rob recalled. “‘Let’s take care of our family. This is not worth it.’” During that visit Barack and Michelle also went for brunch to the home of old Harvard friend Julius Genachowski and his wife, and afterward Barack confessed to Julius that Michelle had asked him, “When are we going to have a life like that?”
In late July and again in August, Barack signed off on twenty-eight different “member initiative” projects, committing a total of $1,080,000 in state funds to a wide range of South Side organizations. Twenty-five of the grants ranged in size from $2,500 to $50,000. The three larger ones provided $100,000 each to the South Side YMCA and to Father Mike Pfleger’s St. Sabina Church and $450,000—up from the $400,000 announced just before the congressional primary—to Wellington Wilson’s Kennedy-King College. Speaking to the Hyde Park Chamber of Commerce, Barack turned from legislative issues to describe his daughter Malia. “She’s such a little sponge right now, she’s soaking everything in. I know she’ll be able to compete at any level because she’s had well-educated parents,” but “that’s not the case for most children.” Barack’s role as cochair of JCAR led the progressive Woodstock Institute to recruit him to take the lead in pressing Governor Ryan to order the state’s Office of Banks and Real Estate, and the Department of Financial Institutions, to strengthen predatory-lending regulations, which a recently passed bill had instructed them to draft. Meeting with Ryan in Chicago on August 10, Barack said the executive branch agencies had not lived up to the legislature’s intent, and that JCAR expected to see stronger rules in the near future.
That initiative won Barack front-page attention in both the Chicago Defender and the Hyde Park Herald, and in the third week of August he flew to Los Angeles, where the Democratic National Convention was about to nominate Vice President Al Gore to take on Texas governor George W. Bush in the November presidential election. Unlike many Illinois politicians, Barack was not a member of the 190-person state delegation, but he thought the trip might be helpful because “I was a little depressed.” Barack had reserved a rent-a-car to get from LAX to the Burbank Airport Hilton, where the Illinois delegates were staying, but at the Hertz counter, his credit card was declined and he had to spend “half an hour on the phone” pleading with customer service to increase his credit limit. “Once he got to the hotel he had to increase his debt limit again to get a hotel room,” Senate colleague James Clayborne remembered Barack telling him. At a Monday-evening reception at the Los Angeles County Museum of Art, an Associated Press reporter asked Barack to comment on rumors that state Democrats hoped U.S. senator Dick Durbin would run for governor in 2002. “Dick Durbin is not only the most popular Democrat in the state, but the most popular politician in the state,” Barack replied. But without a floor pass like official delegates received, Barack and Clayborne ended up taking a bus to the Staples Center and waiting for a day pass together. One night they managed to sneak up to the suite level and watched the proceedings from the box of Donna Brazile, Gore’s campaign manager, but Barack found the trip enervating rather than restorative. He was “the guy in the room who nobody knew, but everyone knew didn’t belong,” he recalled a few years later.
Hasan Chandoo recounted a late-summer conversation: “After the election he’s fucked. He’s got no money. He’s maxed out on credit cards.” Michelle would later mention receiving telephone calls from debt collection agents and hesitating to open the mail because of unpaid credit card bills. But with Dan Shomon insistently encouraging him to focus on legislative prospects in the upcoming 2001 session, Barack and Dan revived the “Obama Issues Committee” that had debuted a year earlier at the outset of the congressional race, this time directing volunteers like Will Burns and young attorney Andrew Gruber to “develop bill and research ideas” that Barack could use to introduce legislation in January.28
Barack continued to emphasize that “the state’s commitment to education is lacking,” and in late September he returned to Cambridge for a weekend gathering of six hundred black Harvard Law School alumni. One of his old basketball buddies remembered Barack making some “very poignant” remarks about the challenges of inner-city education, and the conference proceedings recorded him remarking that “what strikes me is how many talented young students come out of law school thinking they have no options.” At the end of that month, a board retreat aimed at rejuvenating Bronzeville’s Hope Center, where Barack’s former aide Cynthia Miller was now program director, showed that Barack’s vision of what the center should be had not changed from years earlier. Barack “underscored the need for a citywide space for the development of leadership and issues strategies within the African American community,” but just as before, other members wanted to retain a Bronzeville focus. “You cannot be organizing in a local community while trying to develop broader coalitions too,” Barack insisted. “There are no local organizations in the Black community capable of shaping the city agenda,” and “what seems to be missing is an overarching strategy for change in the African American community.” Barack said that “citywide doesn’t mean everything,” just that “the conception of what we’re trying to build is not confined by geographic boundaries.” That meant both “public policy change” and “institution building,” but others wanted the Hope Center to remain focused on “changing people’s level of awareness in ways that enable them to improve their daily lives,” a much more modest mission.
Late September was also the start of the law school’s academic year and Barack’s return to teaching after nine months away. He once again offered both Constitutional Law III and Current Issues in Racism and the Law, each unchanged from prior iterations and with the Racism syllabus wrongly stating that the class was being offered during the spring quarter, as it had been up through 1996, rather than in autumn. Con Law drew only seventeen students, while Racism attracted thirty-two almost entirely liberal students in a law school that continued to have even fewer African American students than it had a half decade earlier. “It was a school that didn’t really understand race relations,” one white male 3L explained. It was “stiflingly white male dominated,” a 3L female who would become a partner at a huge international law firm recalled, “the most stifling environment I’ve ever been in.”
Once again, as 3L Stacy Monahan Tucker remembered, whenever a student “tried to reduce an issue to a claim that the ‘right’ result wa
s clear,” Barack “would jump in and masterfully argue the other side—not as though he was playing devil’s advocate, but as if he truly believed these issues were complex and multilayered, and it would be irresponsible to pretend that there were easy or obvious answers.” Barack “seemed to honestly understand and sympathize with the viewpoints of those who took what would be viewed as the more ‘bigoted’ or less progessive position.” Peter Steffen, also a 3L, agreed that Barack “would often argue the more conservative side of the issues” and “was pretty good at keeping a poker face about what he really thought.” At one of the course’s nine weekly meetings someone asked him directly, “Where do you stand on reparations?” and Barack “paused a long time” before responding, “I think there’s a moral case for reparations, but I don’t know that in practice we can actually ever do anything about it in any kind of practical way.” There was no question that Barack remained a “very effective classroom teacher,” but with the final month of classes given over to the students’ group presentations, one woman felt “he outsourced about half the class.” More importantly, as 3L Rachael Pontikes realized, Barack’s syllabus featured 100 percent male authors, causing her to remember that “women’s voices were missing from the class.”29
In the fall, Barack signed off on more “member initiative” grants of state funds to additional South Side groups. In September, $100,000 each went to the Museum of Science and Industry in Hyde Park and to the Chicago Better Housing Association (CBHA) for a six-block-long Englewood Botanical Garden/Education Project that Barack had announced eight months earlier and that was located directly across the street from a CBHA-sponsored housing development. Then, on October 4, he submitted paperwork to award $75,000 to the South Shore Community Partnership Network, a part of Yesse Yehudah’s FORUM—Fulfilling Our Responsibility Unto Mankind—“to purchase computer equipment, print literature and training manuals, and to cover administrative costs for the 21st Century ‘e’-family.com initiative.” Eleven months earlier, Yehudah had handed Obama a bundle of five $1,000 campaign contribution checks from FORUM employees for the congressional race. “Yesse came and kissed his ass,” Dan Shomon explained, and then “yes, he got an earmark.” Three days after Senate Democrats’ chief of staff Courtney Nottage signed off on Barack’s $75,000 request, another five $1,000 checks, this time from arm’s-length Yehudah friends and acquaintances, arrived to help pay down Barack’s outstanding debt. The quid pro quo could not have appeared more explicit, just as was Barack’s knowing descent into Illinois’s “pay to play” culture: in exchange for $10,000 in campaign contributions to a needy candidate who still needed to recoup $9,500 of his own family’s funds from Obama for Congress 2000, $75,000 in state funds had been given to Yehudah’s organization to use at his discretion.30
In contrast was Illinois’s Republican U.S. senator, Peter Fitzgerald. Less than two years into his first term after defeating Carol Moseley Braun, Fitzgerald, on the same day that Barack was submitting the paperwork for Yesse Yehudah’s $75,000 grant, took to the floor of the U.S. Senate to filibuster an Interior Department appropriations bill he feared lacked adequate safeguards to prevent Republican insiders’ corrupt self-dealing in Springfield. Less than a week earlier, Capitol Fax’s Rich Miller had cited Fitzgerald’s “super-strong distaste for the pinstripe patronage crowd and the politicians who cater to them” while writing about “how corrupt this state can be.” Fitzgerald’s fear was that federal funding for Springfield’s Abraham Lincoln Presidential Library and Museum would be handled so that “a bunch of political insiders wind up lining their pockets at taxpayer expense.” He was particularly concerned about Republican insider Bill Cellini, whose behind-the-scenes influence in state party affairs was infamous and whose wife, along with those of Governor George Ryan and House Republican leader Lee Daniels, sat on the Lincoln Library’s board.
Democratic campaign strategist Pete Giangreco praised Fitzgerald, telling Chicago Magazine that “he’s on target about the Lincoln Library—that thing looks like it’s larded up like the proverbial fatted calf.” Poll numbers showed Fitzgerald with better than 62 percent approval among Illinois voters, but publicly trashing his own party’s top state leaders in the most prominent forum imaginable contributed to the belief that Fitzgerald’s reelection in 2004 “is far from a sure thing,” Chicago reported.
In late October, several weeks before the veto session, Barack traveled to Carbondale to deliver a keynote address at a Youth Government Day event at Southern Illinois University, at the invitation of former U.S. senator Paul Simon. Barack began by highlighting how “pervasive in our culture at this point is a cynicism about not just the political process but public involvement generally. We have a tendency to believe that politics is more of a business than a mission.” Barack explained that he held public office because “I feel like meaning in my life depends on me being involved in something bigger than just myself, that unless I hitch my wagon to larger movements of people and the community at large that I’m selling myself short.” Barack joked that “having a law degree allows you to pretend that you know what you’re talking about even though you don’t,” and he complained that “change is awfully slow in the political process,” especially because “particular groups are so much better organized than the public at large.”
Lobbyists, he said, capitalized on a “monopoly of information” in Springfield, where “the degree of partisanship is not based on ideology but simply on the basis of the interests of leadership in maintaining control of their particular chamber.” Barack explained that “your state senator or your state representative has ceded much of their individual law-making power to the leadership” of the Four Tops, who focused on “policing their membership and making sure that they don’t cross the aisle and work as effectively as they might.” Barack was displeased that “our public policy debate isn’t as effective as it should be . . . because we frame things as either/or as opposed to both/and,” but he referred to his days as an organizer in stressing that “it’s important to communicate to people in terms of their self-interest what government and politics” can do for them. Soon after, Paul Simon sent Barack a thank-you letter, commending his “adept handling of the English language” and reiterating that “when the right opportunity presents itself you should be and will be a candidate for state-wide office.”31
In late October, Michelle discovered that she was again pregnant, happy news but also problematic for the possibility, as the Sun Times’ Steve Neal repeatedly wrote, that Barack would be an ideal Democratic candidate for state attorney general in 2002. Dan Shomon joined Paul Simon in believing that Barack should look to a statewide race and procured a batch of “Obama Statewide” buttons to hand out at one Democratic gathering. Barack had passingly mentioned the AG possibility to Jim Reynolds, Judy Byrd, and Marty Nesbitt during an early fall conversation in Nesbitt’s kitchen, but he told them, “I don’t know whether Michelle’s going to put up with another race. Maybe one more.” Yet having a newborn baby at home just as the 2002 campaign schedule began to ramp up would be difficult, especially given how unhappy Michelle was about Barack’s electoral aspirations. In addition, Barack would be up for reelection to the Senate, so any candidacy for another office would mean surrendering the post he already held.
Barack and Dan’s informal issues committee focused on “legislative ideas for the 2001” session, and Will Burns recommended that Barack call for an increase in “the number of charter schools operating in Chicago,” because such schools enjoyed “broad support . . . within the African American community” and would give Barack “school choice credentials in [a] state-wide race.” One week before the presidential election between Al Gore and George W. Bush, Barack devoted a Hyde Park Herald column to the third-party candidacy of Ralph Nader. “I fervently believe in Nader’s right to run in this election. I think he should have been allowed to participate in debates, and I share a number of his criticisms of the major parties.”
Barack kept up a busy,
sometimes hectic schedule of speaking appearances around Chicago, with a panel discussion at Northwestern Law School, a dinner address at the awards ceremony of a legal aid hotline service, and an appearance at the Developing Communities Project’s annual convention. In the presidential election’s confused and uncertain aftermath, with the counting of votes in Florida leaving the winner in doubt, Barack appeared on WTTW-TV’s Chicago Tonight program and said, “the federal courts have no business being involved in this.” While the Republican front-runner’s status was still uncertain, Barack said, “I don’t think this is going to destroy President Bush’s legitimacy in any fashion.”
