Barack sat back before again weighing in. “There is this big slippery slope of folks and communities that are sinking,” he reminded the group. How can organizing help them? “How do you link up some of the most important lessons about organizing … with some powerful messages that came out of the civil rights movement or what Jesse Jackson has done or what’s been done by other charismatic leaders? A whole sense of hope is generated out of what they do. Jesse Jackson can go into these communities and get these people excited and inspired. The organizational framework to consolidate that is missing,” especially given the lack of minority organizers. “The best organizers in the black community right now are the crack dealers. They are fantastic. There’s tremendous entrepreneurship and skill,” all being used to distribute illegal drugs. To help black neighborhoods, “organizing in these communities … can’t just be instrumental … it has to be recreating and recasting how these communities think about themselves.”
After a pause, Barack turned to one of his chief takeaways from his time in Roseland. Harold Washington “was an essentially charismatic leader,” although “his election was an expression of a lot of organizing that had been taking place over a long time.” All indications were that “to a large extent” Washington “wanted to give back to that process. He wanted to give those groups recognition and empower them in some sense,” as he had done so visibly with Mary Ellen Montes and UNO, but “real empowerment was not done.” An African American historian on the panel objected to Barack criticizing Harold Washington. Sokoni Karanja agreed with the angry historian, but Anne Hallett sided with Barack, who pursued his point. “When you have a charismatic leader, whether it’s Jesse Jackson or Harold Washington … there has to be some sort of interaction” that moves all that energy back “into the community to build up more organizing … more of that needs to be done.” Then the conversation shifted, but Obama made one final point: “Organizing can also be a bridge between the private and the public, between politics and people’s everyday lives.”
Barack’s comments revealed how profoundly he disagreed with the worldview of IAF and Greg Galluzzo, and how convinced he was that social change energies should be focused on the political arena. In later years hardly anyone would appreciate the significance of what Obama said that day. Ben Joravsky, a fellow participant who was already on his way to becoming one of Chicago’s most perceptive political journalists, later recalled Obama’s “veneer of cool” but dismissed his comments as those of “a windy sociology professor with nothing particularly insightful to say.” Only journalist John B. Judis, examining this moment many years later, would highlight how Obama had voiced “a litany of criticisms of Alinsky-style organizing” and note that he had “rejected the guiding principles of community organizing: the elevation of self-interest over moral vision; the disdain for charismatic leaders and their movements; and the suspicion of politics itself.” But, Judis wrote, Obama “did so in a way that seemed to elude the other participants,” who objected only to Barack’s remark that Harold Washington had not left behind any tangible political legacy.
Judis mused that even Obama “seemed initially oblivious to the harsh implications of his own words,” but Washington’s fundamental failure should have been obvious to everyone in the room, especially because the mayor’s political base had so quickly fallen apart after his death, leaving Chicago with a white, Democratic machine mayor with an all-too-familiar surname. Six months earlier, Cook County state’s attorney Richard M. Daley had defeated Gene Sawyer in the Democratic primary by 55 to 44 percent, and five weeks later, Daley was elected mayor, besting Alderman Tim Evans, running as an independent, by 55 to 41 percent. Ed Vrdolyak, now a Republican, garnered 3 percent and soon added a sideline as a radio talk show host to his lucrative South Chicago law practice.22
The Chicago trip was also a chance for Barack to spend a weekend with Michelle Robinson, and either then or soon after, he asked her to accompany him to Honolulu over the winter holidays. Back in Cambridge, Barack kept his distance from the burgeoning student protest campaign, despite his friendship with the outspoken Cassandra Butts, who, second only to Rob Fisher, was his best friend in Cambridge. Laura Jehl, who was working with Cassandra on a manuscript for the Harvard Civil Rights–Civil Liberties Law Review, knew that Barack and Rob were “inseparable,” and she also saw how Barack and Cassandra “were around together a lot but they didn’t appear to be together,” as she put it. “It did not seem to be romantic” and “it did not appear to be sexual.” Another female friend concurred: “the vibe they gave off was fraternal.” Laura thought that as attractive as Barack was, “there was also absolutely no body language of him that I was aware of towards anybody,” and other women all agreed: “I didn’t see any sexual energy from him” said one, and “never any sense” at all, recalls another.
On evenings when Barack worked on the Anthony Cook manuscript at Gannett House, he and fellow 2L African American editor Ken Mack often walked to a sandwich shop in Harvard Square for dinner. On several nights, Gordon Whitman gave Barack a lift home and spoke about how he was volunteering at the Massachusetts Affordable Housing Alliance, a Boston group headed by veteran community organizer Lew Finfer. After Barack mentioned his Chicago experience, Whitman told Finfer he should meet him. Finfer called Obama, and they met up one day at a Harvard Square coffee shop. Finfer found Barack “cool” and “dispassionate,” but hoped to interest him in a return to organizing after law school. Barack politely said no. “I have a plan to return to Chicago and go into politics.”
One mid-October night, 3L executive editor Tom Krause, a U.S. Navy veteran who was overseeing the group edit of the Anthony Cook article, hosted a party following a lecture by Alex Kozinski, the well-known federal appellate judge for whom Krause would be clerking after graduation. Krause invited a number of editors of all political persuasions, and Barack attended. Review editors were prized candidates for clerkships with top federal judges like Kozinski, and an astonishing 102 members of the law school’s 1989 graduating class had won clerkships. Each fall 2Ls began eyeing and discussing which jurists they would apply to in the spring, and Ken Mack was astounded when Barack told him one evening that he was so focused on returning to Chicago after graduation that he would forgo applying for clerkships. When this news spread among African American students, there was open disbelief that such a top performer would pass up so prestigious an accolade. Kenny Smith was surprised and impressed, but others sensed an attitude of group disappointment. As Frank Harper put it, there were “these steps you’re supposed to take” and “people thought that he was making a catastrophic error by not clerking.”
Obama was a semiregular presence at BLSA meetings and parties. Cochairing a BLSA committee made him a formal member of BLSA’s executive board, but the group’s style was decidedly informal, with its annual spring conference the one major event requiring time and attendance by its members. After some BLSA gatherings Barack, Ken, and basketball buddies Frank Harper and David Hill would go to a pizza parlor on Mass Ave a bit north of the law school. Often joining them were two new 1Ls. Karla Martin was an African American 1987 Harvard College graduate; Peter Cicchino was white, gay, a year older than Barack, and had spent six years as a lay member of the Jesuits. Cicchino would become a defining member of the school’s public interest community and a landmark figure in the public emergence of gay people at Harvard Law. Karla remembers Barack saying that he “wanted to be a change agent” notwithstanding his absence from student protest ranks. “It was clear he had ambitions,” but “how that was going to play out was not clear.”
Barack continued to spend more time on the basketball court than he did just hanging out. The new 1L class brought some new faces plus a familiar one into Hemenway gym’s late-afternoon mix. Nathan Diament, an honors graduate of Yeshiva University, was short and fast. Greg Dingens had played defensive tackle at Notre Dame and three times won Academic All-American honors before graduating magna cum laude in 1986. Tom Wathen had been NYPIRG’s executive director during Barack’s four-month stint at City College four years earlier. Wathen recalled that they both did “a double-take” when they first saw each other. Compared to early 1985, when Barack was twenty-three years old, he of course seemed “more sophisticated” now at twenty-eight. “I was very impressed with him,” Wathen remembered.
One day early that fall, Frank Harper, cochair of BLSA’s community