Barack Obama arrived in Chicago in 1985, after answering an ad for a community organizer in a publication called Community Jobs, which he’d picked up one day at the New York Public Library. Gerald Kellman, founder of the Developing Communities Project, was looking for a black organizer to take over the project, which worked in the far-south-side neighborhoods of Roseland, Altgeld Gardens, and Golden Gate. Kellman interviewed Obama in New York and hired him on the spot.

The DCP’s most dedicated volunteers were three women that Obama portrayed in Dreams From My Father as Angela, Mona, and Shirley. The real names of these “Obama Mamas” are Loretta Augustine (now Augustine-Herron), Margaret Bagby, and Yvonne Lloyd.

Edward McClelland is a former Reader staff writer currently working on a history of the Rust Belt. Young Mr. Obama is his third book.

Barack Obama’s very first followers were a trio of middle-aged women who sat on the DCP’s board. Their backgrounds could not have been more different from Obama’s—or more similar to the great majority of blacks who had grown up in the segregated America of the 1940s and ’50s. Loretta Augustine was a native south sider; Yvonne Lloyd a southerner, from Nashville; Margaret Bagby a country girl from a small Michigan town that was a remnant of the Underground Railroad. All three lived in Golden Gate, the neighborhood of aluminum-clad ranch houses alongside Altgeld, and all were married to men with blue-collar jobs: Augustine’s husband was a postal clerk, Lloyd’s was a cop, Bagby’s a UPS driver. Augustine, the youngest, was a cherubic woman who had lived several years in Altgeld during the early years of her marriage. But by the time Obama arrived to head DCP, that marriage was breaking apart, and she was spending more and more time on community activism. That was one reason she became the group’s president. Lloyd, thin and sardonic, was the mother of 11 children, several of them born before Obama. Bagby, a quiet, heavyset woman who had joined DCP after seeing several steelworker neighbors lose their jobs, also had sons older than her kid organizer.

At one point, all the women asked themselves the same question: why am I following this child? When Gerry Kellman had been their organizer, they’d dutifully followed his orders, figuring it was for the good of the neighborhood. With Obama, it was different. They wanted to do what Barack told them to do because Barack told them to do it. The DCP was responsible for its own funding, through church dues and grants, which meant going to foundation boards and asking for money.

“We’ve got to have funding,” he’d tell the group, in meetings at Holy Rosary, the Catholic church on 113th Street where the DCP had its offices, and then he’d tick off the names of groups that might give them money—the Woods Charitable Fund, the Joyce Foundation, the Wieboldt Foundation—astonishing everyone with his knowledge of the bureaucracy and the research he’d done during the few spare hours he wasn’t hauling his ass from meeting to interview to meeting to church service. Lloyd wondered if he ever slept.

“Barack, why don’t you make the presentation?” Lloyd would ask him wearily, before yet another plea for funds.

“Oh, no,” Obama would say. “This is your neighborhood. You feel this inside. You’re going to have to go and talk to these people.”

That was a tenet of community organizing he’d learned from Kellman: you could lead people but you couldn’t do the work for them. Obama would call downtown to set up the appointments, and then he’d drill the women there at Holy Rosary, telling them exactly what to say to those white board members who had millions of dollars to hand out. His favorite words of advice were “stay focused. If everyone around you is acting the fool, screaming and hollering, you stay focused.” On the day of big presentations, he’d drive them to the meeting, all jammed into that rusty blue Honda they thought was the hooptiest car they’d ever seen.

And damn if they didn’t get the money every time.

That was Obama’s dual nature at work. He was black enough to fit in on the south side, but white enough to believe that if he walked into a room and asked people for money, they would give it to him. To women who’d always thought of their race as a limitation, Obama’s attitude was a new way of looking at life.

Augustine became especially close to Obama—close enough to discuss her personal problems with him when he visited her house on DCP business. She thought he was the soberest, hardest-working young man she’d ever met. That $10,000 a year was blood money because he was working 80 hours a week to earn it. You’d never see him in a pair of jeans, only college-boy chinos and little zip-up boots. You’d never even see him eat, he was so focused. On the way to meetings, Obama would stop his car at restaurants. While the women piled their plates with chicken and mashed potatoes, he ordered a spinach salad.

“Food weighs me down,” Obama explained. “It keeps me from thinking. Makes me sluggish.”

When he was forced to cater a meeting, he brought in sandwiches and chips from Subway. Not only does he have no taste for good food, Lloyd thought, he’s cheap, too.

Augustine figured Obama was carrying 140 pounds on his six-foot-one body. She was so worried about his eating that she invited him to her house for Thanksgiving.

“I’ll be all right,” he assured her.

None of them knew anything about Obama’s personal life because he never invited them to his apartment. Obama didn’t live on the far south side. He lived in Hyde Park, a few blocks from the University of Chicago, in a timeworn courtyard building with ill-fitting windows, chipped paint, and crooked Venetian blinds. It was inexpensive, and it was in an academic ghetto, similar to the neighborhood he’d recently left in New York. Obama quickly discovered the Seminary Co-op Bookstore, an underground warren with sections devoted to such esoteric topics as Critical Theory & Marxism and Christian Theology, and paid $30 for a membership. He lived as ascetically as a philosophy PhD candidate, spending his meager free time reading serious books on history and politics. Kellman gave him a copy of The Power Broker, a 1,300-page biography of urban planner Robert Moses; he considered it the best book ever written on how power-hungry politicians and greedy developers can destroy urban neighborhoods. After finishing Parting the Waters, Taylor Branch’s history of the civil rights movement, he told Kellman, “That’s my story.” But even Kellman became so concerned about Obama’s bookishness and overwork that he urged his protege to get a social life. He didn’t want the young man to burn out.

Obama and Kellman met regularly at the McDonald’s on 115th Street, across the street from the Sherwin-Williams plant. The more Kellman got to know his new hire, the more he understood why Obama sympathized with people whose backgrounds were so different from his own. Like the residents of Altgeld Gardens and Roseland, he was an outsider. Growing up as an American in Indonesia, and then as a black kid in Hawaii, without a mother or a father, he understood what it was like to be different from the surrounding society. Outsiders can take one of two paths: they can ease their dislocation by conforming, or they can rebel. By quitting his suit-and-tie job to become an organizer, Obama had rebelled. He had thrown in his lot with the outsiders. That was why he worked so well with people facing poverty and discrimination. The difference between Obama and the folks in Altgeld was that he could go back to the inside whenever he wanted. He had an Ivy League education. He had opportunities. Kellman was always expecting Obama to quit organizing for a better-paying career.