At the Check, Please! taping, Barack was incredibly relaxed and fabulously personable as he joined a white male firefighter and a white female buyer in discussing Dixie Kitchen and two other restaurants. “I eat there quite a bit,” because Dixie Kitchen offered “savory, tasty food for a good price.” Firefighter Kevin O’Grady had nominated Zia’s Trattoria, in far northwest Chicago, which was “a big surprise” to Barack and his family because it had “terrific” food plus free valet parking. When host Amanda Puck asked Barack what was the worst thing that could happen at a restaurant, he immediately answered “rudeness.”43
In the run-up to the winner-take-all redistricting drawing on September 5, both parties initiated lawsuits, with Republicans seeking federal court intervention into Illinois’s mapmaking and Democrats asking the Democratic-majority state supreme court to exert jurisdiction. One reporter trying to explain the process, whereby the winning party could impose its map to maximize its odds in the 2002 elections, turned to longtime political observer Charles N. Wheeler III. “Whichever side wins, it will be like they’ve won the lottery. The guys who lose, it’s like somebody has just called to tell them their whole family has been wiped out by a serial killer,” Wheeler volunteered.
Ten years earlier, when the Republican designee had pulled one of the two red, white, and blue pharmaceutical capsules from a crystal bowl, rumor spread that the Republican one had spent the previous night in a freezer so that the coldest one could be picked. This time one of two small envelopes would be drawn from a Lincolnian stovepipe hat, and the day before the drawing, a dress rehearsal took place in the House of Representatives chamber at the now-ceremonial Old State Capitol. Democratic secretary of state Jesse White and his deputy Jacqueline Price were joined by Democratic designee Tim Mapes, Speaker Madigan’s chief of staff, and Republican National Committee member Bob Kjellander.
On September 5, the Republicans insisted that the two slips of paper be weighed to ensure they were identical. Ms. Price read out the relevant constitutional language, then tore open a large envelope into which the two slips of paper and two small envelopes had been placed. White stepped out of the room as Mapes signed the Democratic form and Kjellander the Republican one, with each then placing his slip in one of the small envelopes before licking and sealing it. Into the hat the two envelopes went, with both men and then Price stirring and shaking the hat before White reentered to reach in and select the winner. Tearing open the envelope, he read out the name of Democratic choice Michael A. Bilandic, the former Chicago mayor and state supreme court justice. News spread rapidly, and the Chicago Defender’s Chinta Strausberg called Barack. “One of the most important things that results from this is giving us a real possibility of regaining the Senate. . . . If we can pick up a couple of seats, Emil Jones would be Senate President and that would make a tremendous difference . . . in terms of concrete legislation,” Barack emphasized. “If the Democrats controlled the Senate, then all the legislation that we’ve seen blocked over the last several years like racial profiling, FamilyCare will be passed.” Barack’s optimism was well grounded, as were the Republicans’ fears. Two days later Capitol Fax’s Rich Miller reported that while the Republican designee had “licked the edge of the entire flap” on his envelope, the Democratic designee had “licked only a portion of the flap.”44
When the legislature was not in session, JCAR’s monthly meetings took place at midmorning on the first or second Tuesday of each month, on the sixteenth floor of the Thompson Center, in the Chicago Loop. On September’s second Tuesday, JCAR members were on their way downtown for the 10:30 A.M. CST meeting. Republican senator Brad Burzynski took a METRA train in from his suburban home, and fellow Republican Doris Karpiel was driving in from Carol Stream. Barack was headed northbound on Lake Shore Drive “when I heard the news on my car radio that a plane had hit the World Trade Center.” On the sixteenth floor of the Thompson Center, Emil Jones Jr. and his two top staffers, Courtney Nottage and Dave Gross, were reviewing the proposed map of new districts with John Corrigan.
As soon as Barack reached the sixteenth floor, news spread that a second plane had hit the other tower, and the Thompson Center was evacuated. “We were all outside, and a lot of people were looking up at the Sears Tower,” Chicago’s tallest building, “thinking that it might be coming down,” Barack recalled. He headed to Miner Barnhill’s nearby office, where everyone was crowded into the basement conference room to follow the news on television. “We watched that horrific scene of the buildings coming down,” and that afternoon Barack drove home. That night Malia and Michelle turned in well before Barack and baby Sasha. “I remember staying up late into the middle of the night burping my child and changing her diapers and wondering what kind of world is she going to be inheriting.”
When the Hyde Park Herald surveyed local politicians for their comments on the September 11 attacks, Barack replied that “the essence of this tragedy, it seems to me, derives from a fundamental absence of empathy of the part of the attackers: an inability to imagine, or connect with, the humanity and suffering of others.” Following Sasha’s birth, Barack and Michelle’s increasingly spotty Sunday attendance at Trinity United Church of Christ had declined even more, so on September 16 they were not present to hear Rev. Jeremiah Wright deliver a sermon titled “The Day of Jerusalem’s Fall.” Assailing how the U.S. government had “supported state terrorism against the Palestinians and black South Africans,” Wright echoed Malcolm X’s famous remark following John F. Kennedy’s assassination to warn that once again “America’s chickens . . . are coming home . . . to roost!” Barack was seeing much less of Wright than he had in earlier years, and Wright had no memory of discussing Barack’s 1999–2000 congressional race with him. On September 16 Wright was only six days away from his sixtieth birthday, and across black Chicago there was tremendous regard for how he had built Trinity into one of the city’s preeminent churches. In an op-ed tribute in the Sun-Times, DePaul professor Michael Eric Dyson lauded Wright as “one of the most intellectually sophisticated and scholarly ministers in the land.”
In a horrible accident of timing, Barack’s good friend Bill Ayers had just published Fugitive Days, a memoir of his Weather Underground involvement thirty years earlier. On the morning of September 11, a prominent New York Times feature story began with a powerful quote: “I don’t regret setting bombs,” Ayers said. “I feel we didn’t do enough.” Bill had previously made similar comments, telling the Chicago Reader’s Ben Joravsky in 1990 that “if anything, we didn’t go far enough. . . . I wouldn’t act any differently. . . . I wouldn’t change a thing.” But in the aftermath of September 11’s almost three thousand deaths, Ayer’s embrace of purposeful political violence seemed beyond callous. In a Chicago Tribune Magazine profile that same Sunday, Ayers struck an entirely different tone. “We were young and stupid. We allowed our organization to slip into a kind of dogma, a kind of self-righteousness, and there’s something dangerous and deadly about that. So, did we make huge mistakes? Yes.” But thoughtful remarks like those received little attention as denunciations rained down upon one of Barack and Michelle’s ten or so best friends in Hyde Park.
After September 11, Barack “was a wreck,” one close acquaintance recalled, and the obvious rhyme—Osama and Obama—now made what was already a highly unusual ballot name an indelible echo of the world’s most notorious terrorist. In what may have been his most depressed moment in more than sixteen years, Barack did something he had not done in almost a decade: he wrote “a long beautiful sad letter” to Sheila Jager. She had completed her University of Chicago Ph.D. dissertation—“Narrating the Nation: Students, Romance and the Politics of Resistance in South Korea”—in December 1994, three years after she married U.S. Army intelligence officer Jiyul Kim. Sheila’s father Bernd was just as dismissive of Jiyul as he had been of Barack in 1986, but by late 1994, Sheila and Jiyul’s first child, Isaac, had arrived, soon to be followed by sister Hannah.
Over the next four years, Sheil
a published a trio of academic articles drawn from her dissertation while readying the revised manuscript for publication as a book. A recipient of no few fewer than eight notable research grants, by September 2001 Sheila was Henry Luce Assistant Professor of East Asian Studies at Oberlin College in northern Ohio. Jiyul, now an army colonel, had been at work in the Pentagon when the third of the hijacked airliners slammed into the building on the morning of September 11. Hearing the news, Sheila rushed to Isaac and Hannah’s elementary school and took the children home. “We didn’t hear from him for a couple hours, and my mom was silent,” Isaac recalled just before entering the U.S. Military Academy at West Point as a member of the class of 2016.
Barack’s long letter made clear that “he was really down and out,” Sheila recalled. Barack recounted his unsuccessful congressional race and described the “impact of 9/11” on him. “I remember distinctly how forlorn he sounded,” but Barack’s real purpose in writing her was to express how much their love still meant to him. He “reconfirmed his thoughts and feelings” even “after ten years of silence,” and Sheila was deeply touched that “the nature of the relationship, Barack’s thoughts and feelings about it” had “continued post-Chicago” all the way to September 2001. She wrote back, updating him on everything in her life, and Barack replied with “a brief letter acknowledging my response to his first letter. . . . He seemed genuinely happy to know that I was doing well and the tone was far more upbeat.”
Seven years later, during a joint interview with Michelle, a questioner asked Barack, “Did you ever have a ‘Can this marriage be saved?’ moment?” “Sure. I mean, you know, look. We had—” Barack responded, to which Michelle interrupted forcefully by asking, “We did?” causing Barack to backpedal. “Oh, I mean . . . no, no. No, no, no, no. But there’s no doubt that there were some strains there” because “we were still paying off student loans, and we’d be short at the end of the month sometimes.” In a subsequent joint interview, Barack attempted to walk back his spontaneous honesty, insisting that “there was no point where I was fearful for our marriage,” but his outreach to Sheila reflected just how despondent Barack was in the aftermath of 9/11.45
On Monday, September 17, Senate Democrats unveiled their new districts map, and it was an over-the-top partisan humdinger, one “that guarantees severe GOP losses in next year’s election,” the Chicago Tribune reported. It placed fourteen of the Senate’s thirty-two Republican incumbents into seven districts, with either retirements or primary contests to follow, while creating nine districts without incumbents. Barack told the Hyde Park Herald, “it’s hard to overestimate the impact the new map will have on policy making in every area.” He acknowledged that “redistricting is never fair—it’s a partisan process—but the lottery is as good a process as any.” With the “continued consolidation of African-American base” uppermost in his mind for whatever race he might next run, on Sunday evening, September 23, Barack drove to Roland Burris’s South Side home, where he joined African American congressmen Bobby Rush and Danny Davis plus Senate colleagues Rickey Hendon and Donne Trotter in endorsing Burris, rather than former Chicago schools chief Paul Vallas, in the Democratic race for governor.
The next morning the U of C Law School’s autumn quarter got under way, with Barack again teaching Con Law III and Current Issues in Racism and the Law. Con Law drew more than sixty students, with many again impressed that Barack, in contrast to some UCLS professors, had no doctrinal or ideological agenda to propound. One day a self-confident student responded to a query Barack had posed by stating that “the more interesting question” involved something else. Classmates nervously wondered how Barack would respond. He paused and smiled. “The more interesting question, huh?” he said as everyone laughed. Classroom moments like that created “a very comfortable environment” where quieter students were encouraged to participate and “students who wanted to do tons of ranting” were kept in check.
Barack’s Racism and the Law drew almost thirty students, and that fall, more than ever before, racial profiling was a front-and-center issue. One Indian American student whose male family members had been repeatedly targeted by Transportation Security Administration saps remembered Barack leading “a very vibrant discussion” of the issue. At a school that even self-conscious white males viewed as a “utopia for white men,” the few black male law students were regularly stopped by security guards even after previously introducing themselves to the officers. In class, Barack was “a very fair, even-handed” teacher, “an excellent law professor at a school that really prides itself on the quality of the teaching.” Byron Rodriguez, a 3L, had just taken a course with the well-known feminist Catharine MacKinnon, which “was just so painfully one-sided” because “you couldn’t disagree with her at all, and Obama was completely in the opposite direction and would really challenge folks of all stripes.” Indeed, “I remember him defending, in the way a law professor would, [Robert] Bork’s position on the Civil Rights Act” of 1964, which the noted conservative had argued at the time was unconstitutional.
Students found Barack an uncommonly sympathetic professor outside of class as well as in it, even though he spent far fewer hours in the building than any other full-time instructor. One day after class, walking to the parking lot, Barack spoke to 2L Bethany Lampland, who had “taken on incredible loans” and was feeling “tremendous pressure to find a career that was fulfilling.” Having recognized “how unhappy I was,” Barack gently asked, “Are you happy here?” with “such an earnest, sincere,” and “disarming” tone that Bethany unburdened herself. “I’m really unhappy. I’m really miserable, and I’m really scared because I only have a year left, and I don’t like this at all, and I’m really afraid that I’m not going to like being a lawyer, and I don’t know what else to do with my life.” As an experienced law teacher, Barack posed the perfect question: “Did you go straight through?” When Bethany nodded yes, Barack described how Michelle had gone directly from college to law school and had had a much less fulfilling experience both at Harvard and in law practice than he had. But “‘going to the University of Chicago Law School is a really big privilege, it’s not a set of handcuffs,’” Barack told her. “He talked about how there were many, many ways that I could use the experience of going to law school even if I never practiced law that could be as meaningful or more meaningful than becoming a traditional lawyer, and that he had a lot of confidence that because I was struggling with this so much at such a young age that I would find the right path,” Bethany recounted years later. By then she was leading one of New York’s largest charity organizations, and that conversation with Barack in the parking lot “really stayed with me.”46
On WTTW’s Chicago Tonight, Barack said that new federal detention proposals were “most troubling” because they targeted only noncitizens. “I’m always more concerned about encroachments on civil rights or civil liberties that apply selectively to people. When they apply to everybody, there tends to be a majoritarian check.” Barack said he supported slightly broadened wiretapping rules, but emphasized that “the crucial issue here is do we have judicial oversight of some sort” for government surveillance. By late September, Senate Democrats had moderated the political pain their new, now slightly revised map would impose on Republican incumbents, but Republicans believed the new map guaranteed Emil Jones at least twenty-nine of the Senate’s fifty-nine seats and perhaps as many as thirty-four. Barack’s district would remain centered on Hyde Park, but rather than running westward to encompass so much of deeply poor Englewood, it would instead run northward along the lakefront, taking in not only Kenwood and Oakland but also wealthy neighborhoods like Streeterville and some of the Gold Coast, north of the Chicago River. The underlying rationale, as John Corrigan and Barack both knew, was to make his district less African American so that those voters could prove useful elsewhere, but the remap also gave him “some really interesting new friends,” as savvy city lobbyist Bill Luking put it. The redistricting process moved forw
ard, with a three-judge federal court quickly dismissing a Republican challenge to the lottery procedure, but Barack’s attention was completely distracted when a sudden medical emergency threatened the life of four-month-old Sasha.
One night Sasha “would not stop crying,” Michelle explained, “and she was not a crier, so we knew something was wrong.” At dawn they called Sasha’s pediatrician, who immediately suspected Sasha had meningitis and told Barack and Michelle to take her right away to the U of C Medical Center’s emergency room. There Sasha underwent a spinal tap and was placed on antibiotics. “We didn’t know what was wrong, and we were terrified,” Barack recalled. “Michelle and I spent three days with our baby in the hospital,” with “us not knowing whether or not she was going to emerge okay.” But the immediate treatment succeeded, and Sasha was discharged with no harm to her long-term health.
On October 11, Barack’s state campaign fund-raiser took place at the South Shore Cultural Center. Barack still confronted his congressional debt, and just a week earlier, he had sweet-talked a brand-new acquaintance, Northwestern University business professor Steven Rogers, into contributing $2,000—in his and his wife’s names—to Obama for Congress 2000 as well as $1,000 to Friends of Barack Obama. The congressional donation allowed Barack to pay himself and Michelle back a second $2,000 for the personal funds they had loaned the campaign eighteen months earlier, following an initial repayment in early spring, and by the end of the year, the debt would be down to only $8,830, $5,500 of which was owed to Barack and Michelle. For his state committee fund-raiser, Dan Shomon and Laura Hunter had assembled an almost fifty-person “host committee,” and the Hyde Park Herald reported that “supporters showed up in droves” at the October 11 event. Many of the host committee members, who gave $1,000 or $1,500 apiece, were old friends and colleagues like Elvin Charity, Jeff Cummings, Valerie Jarrett, and Peter Bynoe, and $1,500 apiece also came from John Rogers at Ariel Capital and Louis Holland of Holland Capital, two of the firms most involved in Barack and Michael Madigan’s initiative to reform state pension investment practices. The beneficent Robert Blackwell; old mentors Newton Minow and Abner Mikva; present and past law firm colleagues Judd Miner and Allison Davis; top congressional supporters Jim Reynolds, Judy Byrd, and Marty Nesbitt; school executive Tim King; former student Jesse Ruiz; and fellow Joyce Foundation board members Carlton Guthrie and Paula Wolff were also on the host committee list. Including a total of more than $20,000 from PACs, by the end of the year Barack’s state campaign committee boasted a balance of more than $93,000, its healthiest amount ever.47
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