Asif knew Sheila as “a very wonderful, wonderful person,” someone who was “passionate” about her work as well as her relationship with Barack. One evening the three of them accompanied Asif’s girlfriend Tammy Hamlish to a talk that her aunt Florence Hamlish Levinsohn, an outspoken local writer, was giving. Three years earlier Levinsohn had published a “patchy, parochial, frankly admiring” biography of her university classmate Harold Washington just after his election as mayor. Tammy had wanted Asif to meet Aunt Florence, but the evening quickly devolved into an unmitigated disaster. Asif remembered that he “started giggling at what the lady was saying, and Barry and I made eye contact, and that was fatal, because then for the next ten minutes we kept uncontrollably giggling and couldn’t control it and almost falling off our chairs because what the lady was saying was just absurd. And neither of us could control it, and because we were sitting next to each other and kept making eye contact, we’re triggering each other over and over and over. Tammy meanwhile is turning red,” and Levinsohn took note of their behavior too. She “was most upset” and “Tammy was mortified,” Asif recalled.
Apart from that embarrassing scene, Barack and Sheila were familiar faces at anthropology graduate students’ occasional parties. Sheila Quinlan, a Reed College graduate who was a year ahead of Sheila, remembered how “everyone thought they were a very sincere couple.” Barack was “quiet,” “friendly,” and “a sweet boy.” Indeed, as Chin See Ming put it, Barack “fit into the scene,” just as he likewise had learned to do in Roseland and even down in the Gardens. Jerry Kellman watched as Obama comfortably embraced his dual lives. “He found a way to be part of the black community and live beyond the black community,” Kellman explained. “He discovered he could live in both worlds.”35
But in December 1986, and for almost two years thereafter, the looming and overarching question was whether Barack Obama could live in both worlds with Sheila Miyoshi Jager as his wife. Five months earlier, before asking Sheila to live with him, he had inquisitively questioned Arnie Graf about the long-term dynamics of interracial marriage and raising half-black, half-white children. And although most passersby and even most anthropology students would not see them in such a way, Sheila knew that “Barack is as much white as I am.” With her half-Japanese ancestry paralleling his half-Kenyan, she and Barack were equally white—one half apiece.
“Marriage was THE vital issue between us and we talked about it all the time,” Sheila explained more than two decades later. Barack “kept work matters and his private life separate,” so their marriage conversations, while known to Asif, were not something Kellman, Kruglik, Tom Kaminski, or Cathy Askew ever heard about from someone so “very private” as Obama. In their time alone together, Sheila saw someone whom no one in DCP ever did, someone with a “deep seated need to be loved and admired.” In their evenings at the spacious apartment on South Harper, Barack read literature, not history, while Sheila had more than enough course readings to occupy her time. And, of course, there was another dimension as well. Barack “is a very sexual/sensual person, and sex was a big part of our relationship,” Sheila later acknowledged.
Everything had come together fast. In “the winter of ’86, when we visited my parents, he asked me to marry him,” Sheila recounted. Mike Dees, her father’s closest friend and Sheila’s virtual uncle, had been told by Bernd in advance that Barack was a prospective son-in-law. “He and Sheila . . . were going to get married,” Dees explained. “They were coming out, they wanted to get married, and so they called me to come up and look the guy over and see what I think.”
One day right after Christmas Mike drove up to Santa Rosa, and “I ended up with Barack for an afternoon,” he recalled. “We just visited.” Barack was clearly a “very bright guy,” and, complexion aside, came across like “a white, middle-class kid.” Then, after dinner, Bernd and Mike had “a big political thing with Barack” while Sheila and her mother Shinko were occupied elsewhere. The two older men and Barack found themselves on “completely opposite sides of the fence,” Mike explained, because “we’re both conservative Republicans.” Barack “kind of thought he was going to lecture to us” about politics and ideology, “and we kind of shot him down.” It got “really heated” and “went on for quite a while.” Barack seemed “very taken aback by it,” Mike recalled. “Barack kind of thought he was going to sit down and get anointed. He’s very self-centered, and he ended up getting beat up.”
Although Barack “didn’t do very well,” to Mike “it was just a political argument. I think to the father and Barack it was more than that,” indeed, much more. “For Barack it was a big deal, for Bernd it was a big deal,” because Barack “was going to be the chosen one that night, and it didn’t work out” that way. It was readily apparent that the older man was sitting in judgment on the younger, perhaps not so differently from the time twenty-five years earlier when Stan Dunham had first met Barack Obama Sr. But here the verdict was negative, not positive. “I don’t know whether his color entered into the picture or not,” Dees said about Bernd’s attitude toward Barack.
By the end of the evening, and again the next morning, Bernd made his view of Barack and his marriage proposal crystal clear. “Bernd was against it,” because he felt that Barack was unworthy of his daughter’s hand. Sheila remembers that “my father was concerned over his ‘lack of prospects’ and wondered whether, as a community organizer, he could even support me, something that deeply offended Barack. My mom liked Barack a lot, but simply said I was too young” to get married. “I went along with their judgment, basically saying ‘Not yet,’” she recalled. The unsettling holiday visit concluded, and “they ended up going back without getting married,” Mike Dees affirmed.
Barack and Sheila would revisit that decision again and again over the twenty months that lay ahead.36
During the first week of January 1987, Gamaliel held a three-day retreat for its seventeen organizers, plus Ken Rolling from Woods, at a Holiday Inn in south suburban Matteson. More important, Obama was now meeting for at least an hour a week, one on one, with Greg Galluzzo to talk about his Developing Communities Project work. Greg’s monthly calendar recorded the regularity of their discussions: Thursday morning, January 15; Wednesday lunchtime, the 21st; Friday morning, the 30th. On Wednesday, February 4, they spoke for two and a half hours; on Monday, February 9, for two more. Wednesday, the 11th, Greg came to Barack’s apartment; Tuesday, the 17th, they met for another ninety minutes—ten hours of conversation in just thirty days.
As anyone who knew Galluzzo would testify, he was so intense that no discussion with him ever devolved into idle chitchat. Deeply committed to his belief that “the essence of organizing is the transformation of the person” into someone who was “serious about being a power person in the public arena,” Greg’s self-confidence and challenging interpersonal style was robust indeed. True to the Alinsky tradition, Greg’s insistence that people unapologetically seek power for themselves was completely nonideological and entirely pragmatic: “Find out what people want,” he said, “and then we’ll decide what we’re going to do about it.” He also agreed with the Alinsky tradition of avoiding insoluble “problems” while constantly searching out winnable “issues.” Greg knew it was essential to “learn politics as the art of the possible.” He believed that, properly taught, “community organizers are pragmatists” who firmly appreciate that “in 99 percent of the cases the end does justify the means.” In addition, an Alinsky organizer assumed a dual public and private life. As one veteran put it, “you compartmentalize life and then it allows your consciousness to go to the beach.”37
On the Far South Side, parents in Altgeld Gardens, aided by Barack, maintained their boycott of the Wheatley Child-Parent Center until January 20, when the CPS provided documentation that no asbestos had been found in the school. The boycott energized Altgeld residents’ interest in Hazel Johnson’s People for Community Recovery, and Mayor Washington spoke at a PCR meeting that drew several hundred peop
le. The Tribune reported a new U.S. Environmental Protection Agency study that had found that “more than 20,000 tons of 38 toxic chemicals are emitted into the air each year in the Lake Calumet region on the Southeast Side.” The Daily Calumet reported that Waste Management’s 1986 quarterly earnings were up an astonishing 349 percent, and a WMI representative, Mary Ryan, had quietly begun speaking with interested parties about WMI’s desire to add the O’Brien Locks site as an adjoining landfill to its huge CID dump just east of Altgeld. Ryan spoke first with Bruce Orenstein, UNO’s new Southeast Chicago organizer, and Mary Ellen Montes. “Waste Management would be very willing to bring benefits to the community, gifts to the community, for your acquiesence, your agreement to allow us to dump there,” Orenstein remembers Ryan explaining. He and Lena were intrigued by Ryan’s offer but wanted to ponder what dollar amount would be appropriate and how such a sum should be managed and invested. Ryan also called on George Schopp at St. Kevin, Dominic Carmon at Our Lady of the Gardens, Hazel Johnson of PCR, civic activists ranging from Marian Byrnes to Foster Milhouse, and Obama on behalf of DCP. In mid-February Lena, Bruce, Hazel, and Barack met to discuss how to respond to WMI’s bold initiative.38
But Obama’s top priority in early 1987 was recruiting supporters for his Career Education Network. In addition to Dan Lee, Aletha Strong Gibson, and Isabella Waller, the three DCP members most interested in the proposal, he also discussed his idea with four people he already knew: Dr. Alma Jones, the indomitable principal of Carver Primary School in Altgeld; John McKnight, whom he was getting to know well through Gamaliel; Anne Hallett of the Wieboldt Foundation, with whom he had spoken in November and who had given DCP a $7,500 grant; and John Ayers, a close friend of Ken Rolling’s who had observed DCP’s “Let Loretta speak!” meeting with Maria Cerda and worked for the prestigious Commercial Club. McKnight and/or Hallett suggested that Barack approach Fred Hess, and Hess recommended that Barack introduce himself to Gwendolyn LaRoche, the education director of the Chicago Urban League. LaRoche scheduled a thirty-minute appointment, but her conversation with the “very polite young man” lasted “about two hours.” LaRoche explained that much of the federal and state funding that was supposed to go to schools with high concentrations of poor students was instead being spent on administrative jobs at CPS headquarters. “Barack was very much interested in” how “our kids were being cheated” by CPS, Gwen LaRoche Rogers recalled years later. The Urban League was already sponsoring after-school tutoring programs in churches, an approach that would fit perfectly with DCP’s congregational base.
Obama reached out as well to Homer D. Franklin at Olive-Harvey, a fifteen-year-old community college just north of 103rd Street that was named for two African American Medal of Honor recipients, and to George Ayers at Chicago State University, on the south side of 95th Street. Olive-Harvey would be crucial to Barack’s hope of establishing a job-training program focused upon public aid recipients and especially Altgeld Gardens residents. DCP also won board of education president George Munoz’s agreement that CPS counseling specialists would cooperate with DCP’s effort.
Obama would later say that his Far South Side work was inspired by what he knew about the history of the black freedom struggle during the 1950s and 1960s, and in late January 1987, Chicago’s public television station, WTTW, joined in the nationwide PBS broadcast of the six-part landmark documentary series Eyes on the Prize on Wednesday evenings at 9:00 P.M. These first six episodes covered only the years from 1954 to 1965—a second set of eight programs three years later would include an episode focusing on Chicago’s own 1965–1967 Freedom Movement—but the Defender and the Tribune publicized and praised the early 1987 Eyes telecasts. The Defender also accorded a full-page headline to a review of a new biography of Martin Luther King Jr., calling the book “a magnificent and unvarnished study” based upon “exhaustive research.” Written by one of Eyes’ three senior advisers, the book devoted the better part of two long chapters to King’s role in the Chicago Freedom Movement. Those chapters highlighted how one particular Chicago civil rights activist, thirty-two-year-old schoolteacher Al Raby, had convinced King to come to Chicago and had been at his side throughout every day of the 1966 campaign.
In subsequent years, Raby played a significant role in the 1970 revision of Illinois’s state constitution before running unsuccessfully for 5th Ward alderman in Hyde Park. Eight years later, Harold Washington’s top political adviser, Jacky Grimshaw, persuaded Washington to name Raby his campaign manager for his successful 1983 primary campaign against incumbent mayor Jane Byrne. But as Raby’s longtime closest friend, Steve Perkins, later explained, “Al and Harold just didn’t have good chemistry” and indeed “rarely communicated.” Once Washington triumphed, Raby was “moved aside” and “totally marginalized.” Raby ran for Washington’s now-vacant congressional seat, but the new mayor backed labor veteran Charles Hayes, and Raby’s loss seemingly left him with “no future in Chicago.” He accepted the number two post at Project VOTE!, a trailblazing voter registration organization, and moved to Washington, D.C.
Eighteen months later, in early 1985, Raby returned to Chicago after Jacky Grimshaw convinced Harold Washington to name him as the new head of the city’s Commission on Human Relations. But Al Raby was no one’s bureaucrat. Instead, as Steve Perkins would emphasize, notwithstanding how Al was “an intensely private person,” he was also “a continual talent scout, always looking for new activists with special gifts.” Judy Stevens, Raby’s deputy at the commission, also watched as “he mentored people.” By early 1987 Al was living in Hyde Park with Patty Novick, who two decades earlier had introduced Al and Steve.
One morning Obama joined Patty and Al for breakfast, and soon after, Al called Steve: “he wanted me to come have breakfast with Barack, and so we had breakfast at Mellow Yellow,” a well-known Hyde Park eatery. “Barack was fabulous. He was smart, he was articulate—it was a joy to meet him,” Steve remembered. Patty recalled how “I want you to talk to” was one of Al’s favorite phrases, and one day in early 1987 Raby took Barack to City Hall and introduced him to Jacky Grimshaw, who was serving as Washington’s director of intergovernmental affairs. According to Jane Ramsey, the mayor’s director of community relations, “Al was all over the place,” and Grimshaw can picture Barack that day: “he was a kid,” although a “very serious” one. But Raby was far more influenced by his experiences with King than by city politics. “Al was determined to create a base for a long-term movement,” Steve Perkins emphasizes.39
In early 1987, Harold Washington’s aides were focused on his reelection, and Jane Byrne was mounting a stiff challenge in the upcoming Democratic primary. The mayor’s employment aide Maria Cerda had made a point of renting a portion of Local 1033’s East Side union hall as a new jobs-referral site. Maury Richards said that income “was just totally instrumental in keeping us afloat” and “at a critical time.” Soon Richards was put on the city’s payroll part-time, allowing him to hold the local union together while also staffing the Dislocated Worker Program. Washington needed all the votes he could get in Southeast Side precincts, and Maury was deeply thankful to Washington, whom he described as “a great guy.” Eight days before the election, steel was poured at South Works for the first time in seven months, another small victory for South Side steelworkers.
Just before midnight on February 25, Byrne conceded defeat after mounting a “powerful challenge” to Washington, whose 53.5 to 46.3 percent victory “was much closer than the mayor’s strategists had been counting on,” the Tribune reported the next day. But the headline “Mayor’s Tight Win Just Half the Battle” pointed to the April 7 general election, when Washington would face two white Democrats running as independents: Cook County assessor Tom Hynes, a relative “Mr. Clean” by Chicago standards, and 10th Ward alderman Ed Vrdolyak, the mayor’s worst nemesis. Fewer white voters had turned out to support Byrne than had voted against Washington in 1983, though the mayor’s own white support had barely risen from four years ear
lier. A larger, more heavily white electorate was possible on April 7, but Washington was “a heavy favorite” as long as both Hynes and Vrdolyak remained in the race.40
On the Far South Side, Obama was trying to generate more grassroots support for his Career Education Network idea. Five high schools drew students from major portions of DCP’s neighborhoods: Harlan at 96th Street and South Michigan Avenue, Corliss on East 103rd Street, Julian at 103rd and South Elizabeth in Washington Heights, Fenger on South Wallace Street at 112th Street, and Carver down in Altgeld Gardens. Barack and a number of DCP’s most active members, including Dan Lee and Adrienne Jackson, began staging modest street corner demonstrations near the troubled high schools to draw attention to the schools’ horrible dropout rates, especially among young black men. One morning that spring, they held a rally on busy 111th Street a block north of Fenger, where one year earlier a Defender photo of the school’s top academic achievers had pictured one dozen African American women. Among the passersby was Illinois state senator Emil Jones Jr., whose office was less than two blocks away. “I stopped to see what they were out there for,” Jones later explained. He knew Adrienne Jackson, and she introduced Jones to Obama. “Barack was part of the group,” Jones recalled. “I met him on the corner.” But Jones was not happy to see protesters just down from the 34th Ward headquarters. “You have a lot to learn,” he told Adrienne and Barack. “You’ll get more flies with honey than you will the way you all are doing this.”
Jones viewed them as an “in-your-face type of group,” but invited them to his office, where they laid out their dropout prevention goals, and particularly Obama’s hope of winning state funding for his Career Education Network. Jones thought Obama was “very bright and intelligent and very sincere” but also “very aggressive and somewhat pushy.” More seriously, Jones thought Obama “was naive as related to the political situation.” He did not know that in most any Chicago ward organization, real power was with the ward committeeman, who often doubled as alderman, and not with state legislators, even one with the grand title of senator. In addition, the Illinois legislature was made up of two very separate chambers.
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