For Barack, much of the session’s final weeks was a cascade of disappointments. He criticized a bill regulating telemarketing calls as being “full of holes,” and at a Chicago forum, he noted how Pate Philip had blocked consideration of his “driving while black” racial profiling bill. “It’s a systemic issue that one person can stifle debate on important issues,” Barack complained. “Walk into a room with one hundred black men, and ninety are going to have stories of being pulled over for biased reasons. Even if 50 percent are mistaken, there’s a real problem out there.” Under the aegis of state attorney general Jim Ryan, Barack and Judiciary Committee colleague Kirk Dillard joined with law enforcement representatives for a series of early-Monday-morning meetings in downtown Chicago to discuss the issue at length, but the conversations came to naught.
Barack unhappily voted present on a bill that would allow Illinois “to commit persons who’ve committed a sexually violent offense after they’ve served their time” in prison. This was “steamrolling what are admittedly odious folks,” Barack warned, and he also voted present on a bill increasing penalties for drug offenders. “We essentially treat the possession of fifteen grams of cocaine in the same way as we treat a violent rape,” Barack argued. “We are currently spending over a billion dollars a year to incarcerate folks, many of whom are nonviolent drug offenders, and we’re keeping them for extraordinarily lengthy periods of time.” In addition, “a disproportionate number of the youths that are sentenced under these laws are African-American and Latino.”
In committee, Barack voted against a bill to expand eligibility for Illinois’s on-hold death penalty to anyone convicted of committing a murder “in furtherance of gang activity,” and when it reached the floor, he said, “What I’m concerned about is for us to single out ‘gang activity’ as a standard that is different from activity involving all kinds of other criminal conduct.” He also worried “that we use this term ‘gang activity’ as a mechanism to target particular neighborhoods, particular individuals,” with race and ethnicity central to the equation. “If we’re going to apply the death penalty, we better make sure that it’s absolutely uniform across the board.”39
That evening the annual capitol skit took place, and Barack’s Senate colleague John Cullerton, a truly gifted mimic, performed “some wicked impersonations of Pate Philip,” Governor Ryan, Emil Jones, and Mike Madigan. “This has been a rough session,” Capitol Fax’s Rich Miller wrote the next morning, “a long, boring and difficult session” that “just hasn’t been much fun.” Tuesday evening was “one laugh riot after another” and a welcome respite. But for Barack the session’s final days were thoroughly downbeat. The Senate unanimously passed JCAR’s resolution endorsing ISBE’s opposition to the new special education rules Judge Gettleman had ordered it to draft. A month later Gettleman mandated that the rules be implemented, and the Seventh Circuit Court of Appeals strongly endorsed his decision, writing that “the district court properly found that the state authorities did not have the power to override an injunctive decree issued by a federal court to remedy a state’s violation of standards established by federal law.”
On May 25, the Senate voted 46–10–1 to approve a new map of Illinois’s congressional districts that representatives of both parties had accepted. Rickey Hendon noted that the boundaries of Bobby Rush and Jesse Jackson Jr.’s districts had been altered so that Donne Trotter and Barack both now lived in the 2nd Congressional District and no longer in the 1st. As Capitol Fax’s Rich Miller described, “Jackson’s district zips up the lakefront in a narrow band and shoots east a few blocks in Hyde Park to pick up Obama’s home.” Barack unsurprisingly voted against the new map. He also joined fifty-seven of his colleagues in supporting $3.5 billion in loan guarantees for new coal plants in southern Illinois, stating, “I am a strong supporter, I think, of downstate coal interests and our need to prop up and improve the outputs downstate,” environmental worries notwithstanding.
Behind closed doors, the Four Tops and Governor Ryan agreed to the state budget for the upcoming fiscal year, and on the last day of the session, Barack joined in its unanimous passage, although he expressed regret that KidCare had not been expanded to include the children’s uninsured parents. “I’m disappointed that 200,000 working moms and dads will have to go another year without health insurance because we couldn’t find $7 million this year and $60 million next year out of a $50 billion budget.”40
With the session over, the big news for the Obamas was the birth on June 10 of Natasha Marian—“Sasha”—her middle name honoring Michelle’s mother, as Malia’s had Barack’s. But a serious family problem loomed nearby, for Michelle’s brother Craig and his wife Janis, parents of nine-year-old Avery and five-year-old Leslie, were divorcing. Craig had kept his sister and mother in the dark as he and Janis had grown increasingly apart. Well compensated at Jim Reynolds’ Loop Capital Markets and driving a Porsche 944 Turbo and a BMW station wagon, Craig yearned to leave the world of finance for his real passion, basketball.
During the 1999–2000 school year, Craig had coached the University of Chicago Lab School’s varsity team, and then Northwestern University basketball coach Bill Carmody invited Craig to join his staff. “Here I was, making all this money, but I really wasn’t excited with what I was doing,” Craig recalled. The Northwestern job meant a 90 percent cut in pay, but “I had a passion for coaching,” and “I didn’t have that passion for business.” After “a very painful period when we began living separately in the same house,” Craig moved back to his childhood home in South Shore, living upstairs over his mother Marian.
Things were tense at East View too. “By the time Sasha was born,” Barack later wrote, “my wife’s anger toward me seemed barely contained. ‘You only think about yourself,’ she would tell me. ‘I never thought I’d have to raise a family alone,’” Michelle complained. Barack continued, “I found myself subjected to endless negotiations about every detail of managing the house, long lists of things that I needed to do or had forgotten to do, and a generally sour attitude.” Michelle’s anger at the primacy Barack accorded his political career was understandable. The day after she gave birth to Sasha, Barack hurried downtown for a meeting of an Illinois State Board of Investments (ISBI) subcommittee that had been created several months earlier in response to his and Speaker Madigan’s initiative on behalf of African American investment firms.
In late March, Madigan, Jim Reynolds, and other black executives had made a similar request to the State Universities Retirement System’s board, and ISBI’s staff believed they could increase their use of Illinois-based minority-owned firms without adversely affecting investment earnings. In the interim, Governor Ryan had quietly named two highly sympathetic new members, Robert Newtson and Susan McKeever, to ISBI’s board, and at the June 11 meeting, Reynolds took the lead in thanking ISBI for its efforts while firmly requesting that they formally adopt the 15 percent minority-firm investment benchmark that the African American firms were calling for.
By the time of Sasha’s birth, Michelle had decided to leave her U of C student affairs job once her maternity leave was over. She was unhappy with her life in manifold ways. “I am sitting there with a new baby, angry, tired, and out of shape. The baby is up for that 4 o’clock feeding. And my husband is lying there, sleeping.” She resolved to reorganize her life, taking advantage of her early-to-bed nature whereby she turned in every night at 9:00 P.M., while Barack stayed up past midnight in his small, exceptionally cluttered office at the rear of their condo, which Michelle called “The Hole.” Michelle realized “I was pushing Barack to be something I wanted him to be for me. I believed that if only he were around more often, everything would be better.” But she realized that if she took the initiative to leave home at 4:30 A.M. for an early workout, Barack would have to assume some basic child care tasks. “I would get home from the gym, and the girls would be up and fed.”
Michelle’s transition to a better life attitude was gradual, not instantaneous, b
ut it was aided considerably when she received a midsummer phone call from Michael Riordan, who on July 1 had become the new president of the University of Chicago Medical Center. Riordan’s general counsel was Susan Sher, Michelle’s friend and former colleague from Mayor Richard Daley’s office, and Paula Wolff, Barack’s Joyce Foundation board colleague, chaired the medical center board that had promoted Riordan to his new post. Riordan wanted Michelle to come speak with him about a new community affairs position at the medical center, but she initially brushed him off, citing newly arrived Sasha. Yet Sher pressed Michelle to at least talk with Riordan, and with no babysitter available, Michelle brought two-month-old Sasha along for a conversation during which Riordan agreed to all of Michelle’s requests and convinced her to take up the new post come early fall.
When Maya visited Chicago that summer to see the Obama family’s newest member, she found her brother at a low ebb and asked him what was wrong. “I don’t know. I’m feeling a little frustrated, like I’m not doing what I’m supposed to be doing, that I could be doing more, that I haven’t found my path, my mission. I’m not listening hard enough for my call, and I’m floundering a little bit.” Taken aback, “I started laughing at him,” Maya recalled. “You’re the only guy who could be a state senator, a law professor, and a civil rights lawyer and feel like you’re underachieving!” Barack had bounced back from his congressional loss fifteen months earlier, as his more energized legislative performance during the 2001 spring session had reflected. As he explained five years later, he had convinced himself that “I can lose an election and this isn’t so bad, and I can still serve and do useful things.” But no matter how much effort he had invested from January through May in advancing a plethora of generally modest bills, the meager results had left him “extraordinarily frustrated.” Looking back at what were now five spring sessions, Barack summed up his record in an almost plaintive tone: “I’m very proud of the work that I did, even though people didn’t know I was doing it.”41
With a new baby, a discontented wife, and an energetic three-year-old at home, the balance of the summer was relatively quiet for Barack. On July 4 he took Malia along to Hyde Park’s annual Independence Day parade, for which local politicians dressed up in patriotic costumes. Two weeks later, Barack was on WTTW’s Chicago Tonight to weigh in on the city’s latest political contretemps. In 1999 white alderman Thomas Murphy had been reelected by the 18th Ward’s 85 percent African American population, but now he was being refused membership in the city council’s Black Caucus. The dispute drew national coverage in the New York Times, and the Chicago Tribune supported Murphy, arguing that if a Black Caucus “has any purpose, it is to serve the special needs of Chicago’s African-Americans,” including “those who elected a white man to be their council voice.” The NAACP also backed Murphy, but black political consultant Delmarie Cobb, speaking for the caucus, explained that membership was based on being a “black elected official.” On Chicago Tonight, Cobb reiterated that position, while Barack took a more nuanced stance. “There’s no question that whites can effectively represent blacks, in the same way that blacks can effectively represent whites.” The caucus’s informal status reminded Barack of black law student associations, where an exclusive group could privately discuss issues. “We all aspire to a vision of a color-blind society,” but “what we also have is a reality which is pluralist.”
At the end of July, Barack, Dan Shomon, Will Burns, and Laura Hunter held the first new Obama Finance Committee meeting. The short-term focus was an October 11 fund-raiser at the South Shore Cultural Center, where Barack and Michelle’s wedding reception had taken place, to generate funds for Barack’s state campaign committee. But the real agenda was Barack’s political future. Shomon divided his presentation into two headings: “Opportunities” and “Challenges.” In the first, Dan cited Barack’s “reputation as [a] thoughtful independent,” his “demonstrated success at building multi-racial electoral coalitions,” his “high visibility,” and his “low negatives.” Several priorities loomed: “continued consolidation of African-American base,” “maintain grass roots event attendance through summer and fall 2001,” and “state-wide travel.” “Challenges” began with “congressional campaign debt,” which had been reduced but was not retired. “Family responsibilities prevent statewide bid in 2002,” Shomon wrote, and Barack’s “next major campaign will be for statewide office and must be a winner.” A “well-funded campaign war chest” would make Barack a “serious contender for emerging opportunities,” such as Republican U.S. senator Peter Fitzgerald’s expected 2004 race for reelection. “Attorney General 2006” and “Governor 2006,” presuming no Democratic incumbents, were more distant possibilities, and another congressional bid would occur “only if there are retirements.” But another hurdle, as Barack and Dan well knew from 2000, was “Cost—Examples: 6 weeks of Chicago TV = $2 million,” “seven state-wide mail pieces = $500,000.” The total cost would be “$5 million or above, depending on [the] office sought.”
Barack had raised a little more than $500,000 to challenge Bobby Rush, so he would need a tenfold increase in his fund-raising in order to mount a credible U.S. Senate race. Later that day, at an ACORN leader’s eightieth birthday party, Madeline Talbott and Keith Kelleher were struck by how “really depressed” Barack seemed. Given a Republican-controlled Senate, “I don’t know if I’m going to stick around with this,” he told them, “but I’m thinking of running for something big, real big. I can’t tell you what it’s about, but I’m going to need your support.”
In August, behind-the-scenes tussling about the upcoming state legislative remap intensified, with state representative Lou Jones, Alice Palmer’s old friend, showering Democratic staffers with invective when one map showed her House district overlapping with Barack’s Senate district. House colleague Barbara Flynn Currie knew Jones was “an incendiary person,” and Jones’s hatred of Barack was well known. Two years earlier, when state representative Tom Dart backed Barack in his challenge against Rush, Jones went after “me like you wouldn’t believe” on the House floor, Dart recalled. “The vehemence was unreal,” and the deluge of expletives was “so intense and virulent.” Now John Corrigan, who was drawing the Chicagoland districts, became the target of Jones’s wrath. “The shit hit the fan. I’ve never heard anyone so angry,” Corrigan recalled, “and I knew it all went back to Alice Palmer.”
For Corrigan, the key factor in drawing Cook County’s House and Senate districts was “you don’t want to waste African American voters if you’re a Democrat.” The federal Voting Rights Act, with its mandate to maximize the number of black and Hispanic districts, offered a crucial legal assist. “If the end result also helped to produce a Democratic majority, it was not a bad side effect,” Corrigan explained. Barack described the same principles to Chinta Strausberg for a front-page story in the Chicago Defender. Ten years earlier, when Republicans had won the winner-take-all drawing, the result had been “racial packing,” whereby African American influence was diminished by creating heavily black districts. “An incumbent African American legislator with a 90 percent district may feel good about his re-election chances, but we as a community would probably be better off if we had two African American legislators with 60 percent each.” Black senators as diverse as Rickey Hendon, Donne Trotter, Barack, and machine warhorse Bill Shaw all grasped that point, but neither Margaret Smith nor a number of black House members endorsed it.42
On August 8, Governor George Ryan announced that he would not run for reelection. Saddled with abysmal approval ratings, due primarily to the ongoing federal investigation into the commercial-driver’s-license scandal dating from his time as secretary of state, Ryan’s decision promised a Republican contest between his moderate lieutenant governor, Corinne Wood, conservative Illinois attorney general Jim Ryan, and ultraconservative state senator Patrick O’Malley. On the Democratic side, Northwest Side congressman Rod Blagojevich, whose father-in-law, 33rd Ward alderman Richard Mell, was one of
the machine’s most influential power brokers, had made clear for months that he intended to run. Mayor Richard Daley, who had worked closely with Governor Ryan, loathed Mell, and Barack’s friend John Schmidt had considered a gubernatorial bid before word spread that former Chicago school superintendent Paul Vallas would enter the race. Perennial statewide African American candidate Roland Burris was eyeing a run, but even in mid-June, Capitol Fax’s Rich Miller put his money on the young congressman. “Blagojevich is wowing Democratic audiences all over Illinois, is raising money by the boatload, has support in the African-American community and has a reliable and sizable Northwest Side base.” Blagojevich is “the ‘new’ face of the Chicago machine,” Miller wrote in early August, and “his career has been carefully stage-managed by his father-in-law.”
Now officially a lame duck, Ryan vetoed the “gang activity” death penalty bill Barack had opposed. Lisa Madigan formally announced her candidacy for attorney general, soon to be joined by John Schmidt. Joyce Washington, a well-to-do African American health care executive, announced a run for lieutenant governor and impressed Rich Miller as “a real firecracker and about the most personable candidate running for any statewide office.” At his frankest moments, Miller loathed the true nature of Chicago and state politics, writing one day about “how brutally greedy and inept the mayor’s office is now that all the reformers,” like Schmidt and Vallas, were long gone. “When you work for a guy like Mayor Daley (or Speaker Madigan . . . or President Philip) you might as well be in the Mafia,” Miller added.
Late that summer television producer David Manilow, whose philanthropist parents Lewis and Susan were regular contributors to Barack’s campaigns, recruited him for a pilot episode of Check, Please!, a restaurant-review show where a trio of guests dined at three eateries, each guest choosing one. Barack’s selection, Hyde Park’s Dixie Kitchen and Bait Shop, exemplified just how deeply grounded in Hyde Park Barack and Michelle had become in their eight years there. Barack ate regularly at several local eateries—Bonjour Bakery, Medici, Pizza Capri, and especially Mellow Yellow—and he patronized Hyde Park Hair Salon, Cornell Shoe Service, Golden Touch dry cleaners, plus, on almost every Sunday, he did his grocery shopping at the Hyde Park Co-Op. Many weekday mornings Barack worked out at the Regents Club gym in the Regents Park high-rise condominium before smoking a cigarette outside. One August morning Stephen Heintz, one of the cofounders of the nascent think tank, now named Demos, on whose board Barack had been a usually absent member, and new president Miles Rapoport met Barack in the Loop for lunch. They had flown to Chicago to tell him that “we want this to be a working board,” and Barack quickly agreed that he would step down.
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