One morning in late May, Barack packed up his mustard yellow Toyota Tercel and headed west on the Mass Pike. He left Harvard “with a degree and a lifetime of debt,” he would say years later, but he also left with something else, just as Jeremiah Wright had told him almost three years earlier: “Don’t let Harvard change you!” “I went into Harvard with a certain set of values,” Barack recounted. “I promised myself that I would leave Harvard with those same values. And I did.” Chicago lay almost a thousand miles to the west, but this time Barack knew exactly where he was headed: 7436 South Euclid Avenue, Michelle Robinson’s family home.
Six summers earlier, on that July night at the Fairway Inn, Bob Elia’s monologue had left a homeless twenty-three-year-old feeling existential self-doubt he would never forget. His years in Roseland, in Altgeld, and in Hyde Park had staunched those fears and replaced them with a deep and abiding sense of destiny. But now Sheila Jager, just like Harvard Law School, was entirely in the rearview mirror. This time, as the Ohio Turnpike gave way to the Indiana Toll Road and finally the Chicago Skyway, Barack Hussein Obama knew exactly where he was headed, to the place he knew was essential for the destiny that awaited him: he was heading west, west toward home.60
Chapter Six
BUILDING A FUTURE
CHICAGO
JUNE 1991–AUGUST 1995
The Chicago Barack Obama returned to in late May 1991 was a significantly different city than the one he had left three summers earlier. South Shore, where he would now be living with Michelle Robinson and her mother Marian, was neither the leafy, university-dominated enclave of Hyde Park he knew so well from 1985 to 1988, nor struggling Roseland, where violent crime was increasing. “Upon my return,” Barack remembered, “I would find signs of decay accelerated throughout the South Side,” but solidly middle-class South Shore was generally tranquil.
Far more momentous—and depressing—were the changes that had overtaken Chicago politics. Less than two months earlier, Mayor Richard M. Daley had been reelected to a full, four-year term of office after crushing first West Side African American Cook County commissioner and former 29th Ward alderman Danny Davis 63 to 31 percent in the Democratic primary and then black former appellate judge R. Eugene Pincham 68 to 24 percent in the general election. In the wake of those two landslide victories over well-known opponents, one astute political observer wrote that “Richie” Daley had “totally captured political control of Chicago.” Harold Washington’s political legacy had been almost completely eviscerated.
In addition, 4th Ward alderman Tim Evans, who four years earlier had been anointed as Washington’s rightful successor by Chicago progressives, lost his seat by 109 votes to three-time challenger Toni Preckwinkle, a liberal teacher whom Evans charged was backed by gentrification-oriented developers. That race had been marred by a bizarre backfire when neighboring 5th Ward Democratic committeeman Alan Dobry, a Preckwinkle supporter, had been caught posting racist placards that he said the Evans campaign was distributing so as to turn voters against Preckwinkle, a black woman whose husband was white.
That attempt to embarrass Evans’s campaign set off a citywide controversy, with a pair of Chicago Sun-Times columnists, African American Vernon Jarrett and white Steve Neal, mounting a sustained but unsuccessful crusade to force Dobry’s resignation from his influential ward committeeman’s post. Dobry, a Hyde Park progressive independent whose role in local politics reached back more than two decades, stood his ground based upon his long record of sustained opposition to the Democratic machine. Two years earlier, when local state representative Carol Moseley Braun won election to a countywide post, Dobry had refused to concur in powerful 8th Ward committeeman John Stroger’s insistence that his organizational protégé Donne Trotter be appointed her successor. With the 5th Ward comprising 40 percent of the district, Dobry held the largest hand, but progressive 7th Ward committeeman Alice Palmer, who three years earlier had defeated machine loyalist William Beavers, nonetheless sided with Stroger. Their combined 60 percent share put Trotter in the state legislature, with Dobry casting his 40 percent for famed steelworkers leader Frank Lumpkin.
Less than two weeks after Preckwinkle’s victory over Evans was confirmed, Hyde Park’s sixty-seven-year-old African American state senator, Richard H. Newhouse Jr., who had held his seat for almost a quarter century, announced his departure from the legislature amid press reports that he was suffering from Alzheimer’s disease. Newhouse had been a courageous pioneer in independent politics, defeating a machine loyalist at the height of the Chicago Freedom Movement’s civil rights protests in mid-1966.
Newhouse played a decisive role in making his colleague Cecil Partee the first African American president of the Illinois Senate, and in 1975 Newhouse had been the first black candidate for mayor of Chicago, winning 8 percent of the vote in a protest campaign against longtime incumbent Richard J. Daley. When his friend Harold Washington won the mayor’s seat eight years later, Newhouse stood beside him on the victory podium, holding their hands high, but throughout all those years, the unspoken question always remained “Why, after all this time, is Newhouse still in the first political office he ever sought?”
The answer was simple, and reflected one of the core truths of African American politics: “Newhouse has a white wife,” Kathie, whom he had first met in 1954. Across the South Side, the word on the street was that Newhouse “talks black but he sleeps white,” and one black nationalist explained that “the perception now is that an African American married to a white is unable to give 100 percent to the cause.” Carol Moseley Braun, who for almost a decade had had a white husband, frankly confessed that “an interracial marriage really restricts your political options. The blind reaction of some people is just horrible.” The Chicago Tribune celebrated Newhouse’s “impressive record” and mourned how his retirement “marked the passing of an era for Chicago’s black progressive political movement.”
As with Moseley Braun’s smaller former House seat, the committeemen whose wards made up Newhouse’s Senate district would select his successor in a weighted vote. The 8th Ward’s John Stroger aimed to elevate Trotter, but organization loyalists controlled only 47 percent of the district. Alan Dobry held 30 percent, and together Tim Evans, still 4th Ward committeeman, and the 7th Ward’s Palmer had 23 percent.
Dobry and Evans had long respected Palmer, who had moved to Chicago at age thirty after completing her undergraduate degree at Indiana University and teaching high school English for three years in Indianapolis. With a father who was an MIT-trained architectural engineer, a mother who also was a teacher, and a grandfather who had been a prominent African American physician, Alice Roberts Robinson Palmer’s interest in education had strong family roots. In Chicago she worked at several local colleges while finishing a master’s degree at Roosevelt University. She also remarried, taking the surname of her second husband, Edward “Buzz” Palmer, a former Chicago police officer well known in the black community as one of the cofounders of the pioneering Afro-American Patrolmen’s League.
In 1977 Alice became associate dean for African American student affairs at Northwestern University, and two years later she completed a Ph.D. in educational administration at Northwestern. Her dissertation, “Concepts and Trends in Work-Experience Education in the Soviet Union and the United States,” was a sophisticated and erudite comparative analysis informed by Palmer’s own research in the USSR as well as her readings of both Karl Marx and John Dewey. During the 1980s Alice and Buzz’s travels included a visit to Grenada during the short reign of Marxist revolutionary Maurice Bishop plus multiple visits to Moscow, Prague, and other Soviet-bloc capitals. They founded a Chicago entity called the Black Press Institute, and Alice’s membership in the U.S. Peace Council plus her active role in the International Organization of Journalists indisputably reflected pro-Soviet sympathies. In June 1986 the People’s Daily World, the newspaper of the Communist Party USA, reported that she was “the only Black U.S. journalist to attend the 27th Congr
ess of the Communist Party of the Soviet Union” three months earlier.
By the time of her election as 7th Ward committeeman in 1988, Palmer had left Northwestern for the Metropolitan YMCA, and by 1991 she was heading up the Chicago affiliate of Cities in Schools, a nationwide dropout-prevention program. Her international travels and affiliations attracted no attention or concern in Chicago, and she later said she had run for the 7th Ward post reluctantly, only because her well-known, outgoing husband had declined Harold Washington supporters’ requests to do so. “I was the quiet one,” she explained. “If the well-meaning citizens of Chicago don’t go out and get their hands dirty in political action, then dirty politics will never be cleaned from the streets,” she told her friend Vernon Jarrett, the Chicago Sun-Times columnist.
Alan Dobry and Tim Evans fully agreed that longtime independent Dick Newhouse’s Hyde Park Senate seat could not be filled by someone allied with Stroger’s black Democratic machine. They also concurred that Alice Palmer was the best available individual, and together they called her to make that case. An “initially reluctant” Palmer accepted, and the trio brushed aside Stroger’s argument that they elevate Donne Trotter and name Palmer to his House seat. On Thursday evening, June 6, the committeemen assembled at Stroger’s 8th Ward office. After brief remarks by both Trotter and Palmer, they voted 53 to 47 percent to make Palmer a new member of the Illinois state Senate before making the formal tally unanimous. Five days later, with the legislature’s annual spring session running overtime into early summer, Palmer headed to Springfield and was immediately sworn into office. In the Sun-Times, Vernon Jarrett praised the new senator as “a role model for other individuals of her race who have attained high degrees” and declared that “there are fewer than a dozen individuals in the Illinois Legislature or the City Council who match her combination of academic attainment and commitment.” The weekly Hyde Park Herald commended Palmer’s selection, praising her independence as well as “her dedication to education.” A week later another Sun-Times columnist reported that Palmer was already “getting high marks from legislative colleagues for her baptism of fire in Springfield. ‘She’s jumped right in and is having no difficulty staying in the fast lane,’” one unnamed observer stated. Before the month was out a clearly happy Palmer told the Herald that she “plans to make a career of the General Assembly.”1
Like Hyde Park, Barack’s new home base in South Shore sat squarely within the Newhouse-Palmer Senate district. But to whatever degree Barack noted Alice Palmer’s emergence as a significant figure in South Side politics, his undisputed focus throughout all of June and July was on the Illinois bar exam, which would be administered on the last two days of July at Northwestern University’s law school. Sidley & Austin had footed the tab for the intensive bar review class that Barack, like almost all other applicants, took in the run-up to the highly demanding, two-day test, and on weekdays Barack often accompanied Michelle downtown, studying at Sidley and attending review sessions. Sidley still hoped Barack would join the firm, but at one large summer dinner another guest mistook Barack for a waiter and asked, “Can I have more tea?”
On Barack’s first Saturday back in Chicago, Michelle took him to the wedding of one of her best friends’ younger brother at the family’s Jackson Park Highlands home. To Barack, Jesse Jackson was the former presidential candidate for whom he had cheered back in 1984 in New York; to Michelle he was the father of her friend Santita, and someone she had met many times during her high school years. Twenty-six-year-old Jesse Jackson Jr. was marrying fellow University of Illinois law student Sandi Stevens, and a Jackson family videotape of the happy event captured a glimpse of Barack, whom Santita introduced to her brother.
Marriage was a subject that was also on Michelle Robinson’s mind, but so was the fact that she was increasingly conscious of how unfulfilling she found her highly remunerative work at Sidley. Her close colleague Kelly Jo MacArthur remembered how the view from Michelle’s office on the forty-something floor looked southward, and that unbroken perspective—“That’s where I really come from”—helped fuel Michelle’s “internal dissonance” about her life. “There was always some sense, from the first time that I met Michelle, that ‘I’m not sure that I really belong in this corporate law firm,’” Kelly recounted, and notwithstanding how much relatively interesting work partners like Newton Minow, Charles Lomax, and Quincy White gave Michelle, including pro bono assignments, her dissatisfaction grew. “I couldn’t give her something that would meet her sense of ambition to change the world,” White recalled. Even before that summer, Michelle had quietly begun searching for a new job. One person she sought counsel from was Gwendolyn LaRoche Rogers, the effective stepmother of her brother Craig’s best friend, fellow Princeton graduate John Rogers Jr., who, like Craig, was pursuing a career in finance. Eight years earlier Rogers had founded his own investment firm, Ariel Capital Management, with start-up funds from his mother and a Chicago couple who were lifelong family friends, James and Barbara Bowman.
Four years earlier Barack had approached Gwen LaRoche, the Chicago Urban League’s education director, for help with his Career Education Network, and now Michelle Robinson sought advice too. “Michelle came to me and said that she was not happy at Sidley & Austin. She did not want to be working in a law firm. She wanted to do something for the people,” Gwen LaRoche Rogers explained. Michelle remembered it similarly: “I wasn’t happy” and wanted work with “a community-based feel” that would “benefit others.” She asked Gwen if the Urban League could use her, but Gwen, knowing what Sidley paid, told Michelle that she would cry every night over what the League could afford. So Michelle continued her outreach, realizing that when she asked herself, “Can I get pumped up every day about coming to practice corporate law? The answer was simply ‘no.’”
Barack also knew that even after devoting the next year to writing “Journeys in Black and White,” practicing law at Sidley was not what he wanted to do either, no matter how well it paid. Michelle also was repeatedly raising the question of would they indeed commit to getting married, but throughout June and July, Barack kept putting it off. Then, with Barack’s bar exam complete on Wednesday, July 31, the couple scheduled a celebratory dinner, and Barack chose the stylish, three-star Gordon at 500 North Clark Street, which the Chicago Tribune had praised as one of the city’s best restaurants just weeks earlier and was best known for its flourless chocolate cake. Early in the meal Michelle mentioned marriage, and Barack once again parried. Then, after they ordered dessert, what appeared in front of Michelle was not chocolate cake but a small box. As she opened it and discovered an engagement ring, Barack asked, “Will you marry me?” and Michelle immediately replied, “Yes, yes,” before being rendered otherwise speechless. “I was completely shocked,” she later explained, because Barack’s long-standing equivocation left her truly surprised by his proposal. Whatever Michelle had ordered for dessert was ignored. “I don’t think I even ate it. I was so shocked and sort of a little embarrassed because he did sort of shut me up” after weeks of persistent questioning.
In the immediate wake of Barack and Michelle’s engagement, events moved quickly. Almost simultaneous with their dinner, a copy of Michelle’s résumé made its way to assistant Chicago corporation counsel Susan Sher. Just weeks earlier Sher’s fellow assistant corporation counsel Valerie Jarrett, the thirty-five-year-old former daughter-in-law of columnist Vernon Jarrett and the daughter of James and Barbara Bowman, had been named Mayor Richard Daley’s new deputy chief of staff. Sher, highly impressed with Robinson’s Princeton and Harvard Law School credentials, passed Michelle’s résumé to Jarrett, who responded similarly and quickly scheduled an interview. In person, Robinson was just as impressive as on paper, and as their initial ninety-minute conversation ended, Jarrett spontaneously offered Michelle a job as assistant to the mayor without clearing it with either Daley or her boss, chief of staff David Mosena. Michelle bonded almost immediately with Jarrett—“She understood how I felt. It
was difficult to find people who understood my desire to leave a high-paying corporate job”—but replied that she wanted to think it over. A few days later Michelle called Jarrett and asked, “Would you be willing to have dinner with my fiancé so that the three of us could talk about it?” Jarrett agreed, and an evening or two later, they met up at a seafood restaurant in the downtown Loop.
Valerie Bowman Jarrett’s background was almost as exotic as Barack’s. Five years his senior, Jarrett had been born in Shiraz, Iran, while her father, a pathologist who specialized in blood diseases and abhorred the racial discrimination he had experienced in U.S. medical institutions, was working there for six years. Jim Bowman had met and married Chicago native Barbara Taylor, whose father Robert was the first African American chairman of the Chicago Housing Authority, during a Chicago residency. From Iran, the small family moved to London for one year before returning to Chicago, where Bowman soon joined the University of Chicago’s medical faculty.
Valerie grew up in Hyde Park, completed her secondary education at the Northfield Mount Hermon School in Massachusetts, and graduated from Stanford University in 1978 before entering law school at the University of Michigan and receiving her J.D. in 1981. After six years in private practice with two Chicago law firms, Judson “Judd” Miner, Harold Washington’s corporation counsel, hired Jarrett, and she remained in that office as first Eugene Sawyer and then Richard Daley became mayor. Divorced in 1988 after a five-year marriage to a childhood friend, Vernon Jarrett’s son William, by 1991 Jarrett was a single parent raising a six-year-old daughter and experiencing what the Tribune called a “meteoric rise” in Mayor Daley’s inner circle.
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