As Barack described it to me, he’d been happy in Indonesia and got along well with his new stepfather, but his mother had concerns about the quality of his schooling. In 1971, Ann Dunham sent her son back to Oahu to attend private school and live with her parents. She was a free spirit who would go on to spend years moving between Hawaii and Indonesia. Aside from making one extended trip back to Hawaii when Barack was ten, his father—a man who by all accounts had both a powerful mind and a powerful drinking problem—remained absent and unengaged.
And yet Barack was loved deeply. His grandparents on Oahu doted on both him and his younger half sister Maya. His mother, though still living in Jakarta, was warm and supportive from afar. Barack also spoke affectionately of another half sister in Nairobi, named Auma. He’d grown up with far less stability than I had, but he didn’t lament it. His story was his story. His family life had left him self-reliant and curiously hardwired for optimism. The fact he’d navigated his unusual upbringing so successfully seemed only to reinforce the idea that he was ready to take on more.
On a humid evening, I went with him as he did a favor for an old friend. One of his former community-organizer co-workers had asked if he could lead a training at a black parish in Roseland, on the Far South Side, an area that had been crippled by the steel mill closings of the mid-1980s. For Barack, it was a welcome one-night return to his old job and the part of Chicago where he’d once worked. It occurred to me as we walked into the church, both of us still dressed in our office clothes, that I’d never thought much about what a community organizer actually did. We followed a stairwell down to a low-ceilinged, fluorescent-lit basement area, where fifteen or so parishioners—mostly women, as I remember—were sitting in folding chairs in what looked to be a room that doubled as a day-care center, fanning themselves in the heat. I took a seat in the back as Barack walked to the front of the room and said hello.
To them, he must have seemed young and lawyerly. I could see that they were sizing him up, trying to figure out whether he was some sort of opinionated outsider or in fact had something of value to offer. The atmosphere was plenty familiar to me. I’d grown up attending my great-aunt Robbie’s weekly Operetta Workshop in an African Methodist Episcopal church not unlike this one. The women in the room were no different from the ladies who sang in Robbie’s choir or who’d turned up with casseroles after Southside died. They were well-intentioned, community-minded women, often single mothers or grandmothers, the type who inevitably stepped in to help when no one else would volunteer.
Barack hung his suit jacket on the back of his chair and took off his wristwatch, laying it on the table in front of him to keep an eye on the time. After introducing himself, he facilitated a conversation that would last about an hour, asking people to share their stories and describe their concerns about life in the neighborhood. Barack, in turn, shared his own story, tying it to the principles of community organizing. He was there to convince them that our stories connected us to one another, and through those connections, it was possible to harness discontent and convert it to something useful. Even they, he said—a tiny group inside a small church, in what felt like a forgotten neighborhood—could build real political power. It took effort, he cautioned. It required mapping strategy and listening to your neighbors and building trust in communities where trust was often lacking. It meant asking people you’d never met to give you a bit of their time or a tiny piece of their paycheck. It involved being told no in a dozen or a hundred different ways before hearing the “yes” that would make all the difference. （This, it seemed, was a large part of what an organizer did.） But he assured them they could have influence. They could make change. He’d seen the process work, if not always smoothly, in the Altgeld Gardens public-housing project, where a group just like this one had managed to register new voters, rally residents to meet with city officials about asbestos contamination, and persuade the mayor’s office to fund a neighborhood job-training center.
The heavyset woman sitting next to me bounced a toddler on her knee and did nothing to hide her skepticism. She inspected Barack with her chin lifted and her bottom lip stuck out, as if to say, Who are you to be telling us what to do?
But skepticism didn’t bother him, the same way long odds didn’t seem to bother him. Barack was a unicorn, after all—shaped by his unusual name, his odd heritage, his hard-to-pin-down ethnicity, his missing dad, his unique mind. He was used to having to prove himself, pretty much anywhere he went.
The idea he was presenting wasn’t an easy sell, nor should it have been. Roseland had taken one hit after another, from the exodus of white families and the bottoming out of the steel industry to the deterioration of its schools and the flourishing of the drug trade. As an organizer working in urban communities, Barack had told me, he’d contended most often with a deep weariness in people—especially black people—a cynicism bred from a thousand small disappointments over time. I understood it. I’d seen it in my own neighborhood, in my own family. A bitterness, a lapse in faith. It lived in both of my grandfathers, spawned by every goal they’d abandoned and every compromise they’d had to make. It was inside the harried second-grade teacher who’d basically given up trying to teach us at Bryn Mawr. It was inside the neighbor who’d stopped mowing her lawn or keeping track of where her kids went after school. It lived in every piece of trash tossed carelessly in the grass at our local park and every ounce of malt liquor drained before dark. It lived in every last thing we deemed unfixable, including ourselves.
Barack didn’t talk down to the people of Roseland, and he wasn’t trying to win them over, either, by hiding his privilege and acting more “black.” Amid the parishioners’ fears and frustrations, their disenfranchisement and sinking helplessness, he was somewhat brashly pointing an arrow in the opposite direction.
I’d never been someone who dwelled on the more demoralizing parts of being African American. I’d been raised to think positively. I’d absorbed my family’s love and my parents’ commitment to seeing us succeed. I’d stood with Santita Jackson at Operation PUSH rallies, listening to her father call for black people to remember their pride. My purpose had always been to see past my neighborhood—to look ahead and overcome. And I had. I’d scored myself two Ivy League degrees. I had a seat at the table at Sidley & Austin. I’d made my parents and grandparents proud. But listening to Barack, I began to understand that his version of hope reached far beyond mine: It was one thing to get yourself out of a stuck place, I realized. It was another thing entirely to try and get the place itself unstuck.
I was gripped all over again by a sense of how special he was. Slowly, all around me, too, the church ladies began nodding their approval, punctuating his sentences with calls of “Mmmm-hmm” and “That’s right!”
His voice climbed in intensity as he got to the end of his pitch. He wasn’t a preacher, but he was definitely preaching something—a vision. He was making a bid for our investment. The choice, as he saw it, was this: You give up or you work for change. “What’s better for us?” Barack called to the people gathered in the room. “Do we settle for the world as it is, or do we work for the world as it should be?”