(Washingtonpost.com) 
South Side Childhood

It is not a shy person who sets a bar high, then chooses to lay out her reasoning to audiences and interviewers all across the country, day after day, without notes or evident anxiety. Chicago businesswoman Kevann Cooke, a fellow black Princeton graduate, describes Michelle as "intelligent, thoughtful and a hell of an amazing public speaker. She has the ability to talk to anyone, and that's because she's comfortable in her own skin."

Maybe it was always that way for a woman who jokes that her family wondered what man would be strong enough to win her heart and handle her personality.

For much of her early life, Obama lived on the second floor of a two-family house in South Shore, a predominantly black working-class community near Lake Michigan on Chicago's South Side. Her brother, Craig, says, "If I had to describe it to a real estate agent, it would be 1BR, 1BA. . . . If you said it was 1,100 square feet, I'd call you a liar."

Wood paneling divided the living room into three spaces -- one for Craig's bedroom, one for Michelle's and one for a common study area. For a living, Frasier Robinson tended steam boilers and Marian Robinson stayed home until Michelle was in high school, and achievement was expected, fueled by a certain optimism.

"When you grow up as a black kid in a white world, so many times people are telling you, sometimes not maliciously, sometimes maliciously, you're not good enough," says Craig Robinson, a two-time Ivy League basketball player of the year at Princeton, now head coach at Brown University. "To have a family, which we did, who constantly reminded you how smart you were, how good you were, how pleasant it was to be around you, how successful you could be, it's hard to combat. Our parents gave us a little head start by making us feel confident.

"It sounds so corny," he adds, apologetically, "but that's how we grew up."

Barack Obama says visiting the Robinsons was "like dropping in on the set of 'Leave It to Beaver.' " As the son of a white single mother from Kansas and a largely absent black father from Kenya, he felt he had "bloodlines scattered to the four winds." But he found a sense of place at the Robinsons, where "there were uncles and aunts and cousins everywhere, stopping by to sit around the kitchen table and eat until they burst and tell wild stories and listen to Grandpa's old jazz collection and laugh deep into the night."

The portrait came with a twist: Beset by multiple sclerosis, Frasier Robinson declined from an agile boxer to a man who needed two canes to walk across the street. Craig Robinson says the children never knew their father without a limp, yet saw him report to work uncomplainingly. To the end, he was his family's voice of good sense and authority.

"I remember him saying you don't want to do things because you're worried about people thinking they're right; you want to do the right things," Craig says. "You grow up not worrying about what people think about you."

Except maybe your father.

"If you disappointed my dad," Craig recalls, "everybody was, like, crying."

"I am constantly trying to make sure that I am making him proud -- what would my father think of the choices that I've made, how I've lived my life, what careers I chose, what man I married," Michelle tells an audience. "That's the voice in my head that keeps me whole and keeps me grounded and keeps me the girl from the South Side of Chicago, no matter how many cameras are in the room, how many autographs people want, how big we get."

When Michelle and Barack went on their first date, they saw Spike Lee's "Do the Right Thing."

Ivy League Acclimation

Princeton left Michelle Robinson freshly conflicted about her own ambitions. The picture-book university, with its neo-Gothic quadrangles of carved stone and its clutches of self-assured white people, was an elite realm that delivered an elite education. It was a combination that cut both ways, reminding her too often that she was a black student from the urban working class, while also telling her that Michelle LaVaughn Robinson could play in the big leagues.

"My experiences at Princeton have made me far more aware of my 'Blackness' than ever before," she wrote in the introduction to her sociology thesis, "Princeton-Educated Blacks and the Black Community." "I have found that at Princeton, no matter how liberal and open-minded some of my White professors and classmates try to be toward me, I sometimes feel like a visitor on campus; as if I really didn't belong."

Yet she began to think her time at the university had instilled "certain conservative values." By senior year, she saw herself "striving for many of the same goals as my White classmates -- acceptance to a prestigious graduate or professional school or a high-paying position in a successful corporation."

Her internal debate over her future -- What is possible for a black person? What is desirable? What is acceptable when judged by whom? -- continued at Harvard and Sidley Austin the year her father and college friend died. In her mid-20s, two years out of law school, her answers prompted her departure.

When she began looking for life beyond the law firm, she sought advice widely. A friend sent her resume to Valerie Jarrett, Daley's deputy chief of staff, who interviewed her and offered a job on the spot. Michelle was intrigued, but she asked Jarrett to meet with her fiance. Barack wanted to know whether her ideas would find a home with Daley, the energetic but untested son of Chicago's imperious longtime Democratic boss.

At dinner with the couple, Jarrett came up with the right responses and Michelle went to City Hall in 1991, soon following Jarrett to the city planning department. Later, when Jarrett chaired the Chicago Transit Authority, Michelle volunteered to lead the citizens advisory board. In 1993, she started the Chicago chapter of Public Allies, an AmeriCorps program that trains young people through internships at nonprofits.

"Michelle," says Jarrett, "is really good at taking nothing and creating something."

In 1996, recruited again by Jarrett, she decamped for the University of Chicago and the first in a string of increasingly prominent community service and outreach jobs. She is now vice president for community and external affairs at the University of Chicago Medical Center, a liaison to impoverished and medically underserved black neighborhoods.

There is significant irony in her position. The university is an intellectual haven with broadly liberal politics, yet its sometimes diffident approach to surrounding African American neighborhoods has long been a sore point. A half-century ago, its heedlessness provoked one of the most storied episodes in the career of Saul Alinsky, the iconoclastic community organizer whose mobilizing model was studied and taught by Barack Obama.

In 1960, as the University of Chicago expanded into the black community of Woodlawn, Alinsky mobilized residents to fight back, while also challenging city policies on policing and school segregation. In August 1961, to prove that City Hall should pay attention, more than 2,000 residents boarded 46 buses for the trip downtown. They registered, very publicly, to vote.

© 2007 The Washington Post Company

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