Barack’s embrace of his “destiny,” as he described it to Sheila, had quickened his thinking for the last six months. Kellman’s move to Gary had left DCP entirely in Barack’s hands until he had been able to hire Johnnie Owens, but once Johnnie was on board, Barack’s references to law school—to Sheila, to his close friend Asif Agha, to Asif’s friend Doug Glick on their long drives up to Madison and back—became far more frequent. Early that fall Bobby Titcomb, Barack’s closest Hawaii friend, passed through Chicago, and he remembers Barack talking then about wanting to get a law degree. Asif left Chicago in early November for six months in Nepal, and one October evening, not long before he left, he went to Barack and Sheila’s apartment on South Harper. “We used to cook dinner for each other a lot,” said Asif, and that evening Barack was out on one of his several-days-a-week runs along Hyde Park’s lakeshore. “I was sitting with Sheila in the kitchen, and he walked in all sweaty,” wearing shorts, and “I remember him saying something about his law school essay, and that he had been mulling it over for many days, maybe weeks.” Mary Bernstein remembered Barack mentioning it to her as well. He had cited Harvard in particular to Asif—“his dad went to Harvard,” Asif remembered, “so he had some interest in Harvard” and “that was his first choice.” Asif had not heard what Barack had told Sheila about a “destiny,” but after two years of weekly conversations, he knew Barack “was an ambitious person.”
Several weeks earlier, Jerry Kellman told Obama about a conference titled “The Disadvantaged Among the Disadvantaged: Responsibility of the Black Churches to the Underclass.” It would be held in late October at Harvard Divinity School in Cambridge, Massachusetts, and Barack agreed they should go. The weekend of “study, reflection, and worship,” as the divinity school’s dean termed it, for the two hundred attendees began on Friday evening with a sermon by Samuel D. Proctor, pastor of New York’s Abyssinian Baptist Church and one of the most famous living black preachers. Proctor’s sermon “chilled us,” one listener recounted, with its description of “the ordinary terrors of normal life in Harlem.”
Saturday morning featured a powerful and provocative lecture by Philadelphia congressman and clergyman William H. Gray. “Will we have a two-tiered society of the haves and the have-nots … or will we have a society … that allows people to move from the underclass on up?” Gray asked. For black Americans, “education is an absolute essential,” as the record was clear: “no education, no advancement,” and “blacks with no education have very little hope” of bettering their lives. Gray did not shy from naming other ills. “The leading cause of death among young black males is black-on-black crime. That’s us. Superfly selling drugs and coke in our community is not someone else. It’s us. Those who are mugging us, raping us, and robbing us are not coming from somewhere outside. It’s us. The teenage pregnancy problem is not the white man’s problem, it’s our problem…. You cannot ever escape poverty with children having children.”
Two sets of four concurrent workshops bracketed a lunchtime lecture by sociologist William Julius Wilson. After the workshops ended, Jerry and Barack took a walk around the Harvard campus. “We didn’t spend a lot of time with other people at the conference,” Kellman recalled, “just with each other.” During their stroll, Barack told him that he was applying to law schools. Kellman remembers Barack saying, “ ‘I owe it to you to let you know as soon as I can,’ ” and Kellman recalls being “very surprised.” Kellman also remembers Barack saying he did not think that community organizing was an effective means for attaining large-scale change or a practical method for influencing elected officials who potentially could. Years later Obama described his thoughts similarly, saying that “many of the problems the communities were facing were not really local,” and that he needed a better understanding of how America’s economy worked “and how the legal structure shaped that economy.” He also “wanted to find out how the private sector works, how it thinks.” By “working at such a local level” he had learned that problems like joblessness and bad public schools were “citywide issues, statewide issues, national issues” and he wanted to “potentially have more power to shape the decisions that were affecting those issues.” In a subsequent interview he would specifically cite decisions that “were being made downtown in City Hall or … at the state level.” He had been able to get “outside of myself by becoming a community organizer,” but the experience also had taught him that “community organizing was too localized and too small” to offer significant promise to those it sought to empower.
Saturday night’s dinner speaker was Children’s Defense Fund president Marian Wright Edelman, who one listener said presented a “terrifying analysis” and emphasized the need for “an ethic of achievement and self-esteem in poor and middle-class black children.” Sunday morning the symposium concluded with a sermon by Harvard professor and pastor Peter J. Gomes, who worried that after two days of “some pretty depressing statistics, some very grim predictions, some very sobering analyses” the discussion had become “so intimidating, so daunting as to lead to paralysis rather than action. With more conferences like this, one will be terrified of thinking about any form of response.” But Gomes believed the weekend’s clear message was that “money, programs, and advocacy alone will not solve the problems of the underclass.” Instead, a consensus had identified “despair as the root and fundamental disease: despair, the loss of hope, the loss of any sense of purpose, or worth, or direction, or place,” an analysis all too true to someone familiar not only with Altgeld Gardens but also Chicago’s Far South Side high schools.60
Back in Chicago on Monday, Barack wrote a congratulatory postcard to Phil Boerner, who had announced his upcoming marriage to his longtime girlfriend Karen McCraw. “Life in Chicago is pretty good,” Barack wrote. “I remain the director of a community organization here, and I’m now considering going to law school. Makes for a busy life: not as much time to read and write as there used to be. Seeing a good woman, a doctoral student at Univ. of Chicago.”
The next weekend was the beginning of Gamaliel’s third weeklong training at suburban Techny Towers, with about sixty trainees joining the network’s usual roster of trainers: Greg, Mary, Peter Martinez, Mike Kruglik, Phil Mullins, Danny Solis, and Barack. David Kindler now worked under Mike at SSAC in Cook County’s south suburbs, and Kindler brought his Quad Cities friend Kevin Jokisch to the early November training. “Who you brought to training was a reflection of your ability as an organizer,” Kindler explained, and Jokisch already had hands-on experience.
“Barack was always a great trainer,” Danny Solis remembered. “He had a presence.” After sitting in on two of Obama’s sessions, Jokisch agreed. “Barack was totally in control without appearing to be in control…. His sessions flowed, were all lively, and engaged participants. He drew people out, had them tell their stories in the context of the session he was leading. His style was different than many of the other trainers. Most of the trainers were aggressive, in-your-face types.” In contrast, “Barack and Mary Gonzales had a very similar way of moving, speaking, drawing people out, utilizing humor, and probably most importantly being trusted by those in the room.”
Most nights some of the trainers adjourned to an Italian restaurant and bar just down the road. “Obama showed up twice to have beers with us. The after-hours sessions were very lively,” Jokisch recalled. “Most of the debates were around politics and politicians,” with Barack jumping in. Phil Mullins remembers how Barack “saw the limitations of just pure community organization” and asked, “How do you get at these bigger issues?” Given Gamaliel’s IAF worldview, that meant Barack “was kind of out there on his own,” and he was “constantly asking himself what he actually thinks about something,” another colleague recalled. Phil, like Kindler, also knew that among all the organizers, Barack’s real relationship was with Kruglik. “That’s the tighter person-to-person relationship” for Obama, more so than Jerry or even Greg, Mullins recounted. It was “more personal,” because as everyone