The essential Americanness of Michelle Obama is rooted in her home, the South Side of Chicago. What I originally knew of the South Side I had gleaned from my college years at Howard University. It was the mid-’90s, and all of us sported some measure of black pride—be it Afrocentric or ghettocentric. Often it was a mix of the two. But the South Side kids didn’t boast about rep or whose ’hood was harder. They did not make a scene like the dudes from New York. Instead, they played the South Side rapper Common’s Resurrection until the CD skipped, and walked around campus with their chins in the air, as if they knew something we didn’t. The girls from Chicago were intoxicating—maybe it was the cadences of the South that still clung to their words, or their appreciation for Sam Cooke and Al Green. Ten years ago, I chose my partner from among that lot. Though she spurned her hometown, and the South Side particularly, as a cradle of bougie Negroes, her ties to that magical city still pulled me in.
A few weeks after I saw Obama in Chicago, I came back to town, pushing a white rental through the byways of the South Side. My guide was Timuel Black, 90 years old, who’d fought in World War II, helped bring Martin Luther KingJr. to the city, and, in his later years, turned to compiling an oral history of the Great Migration. A slight, energetic man with a gray mustache, he stepped into the car wearing a blue Obama/Biden hat, and we were off. For three hours, we followed the map of his memories across the South Side, down Cottage Grove, across Hyde Park Boulevard, down through Michelle’s old neighborhood of South Shore. Black was 7 when he saw Charles Lindbergh parading down Grand Boulevard, later rechristened Martin Luther KingJr. Drive. He pointed out Joe Louis’s home, and black Chicago’s old commercial district, the Stroll, where he’d seen all the jazz acts.
The South Side’s sheer mass and its shifting character astonished me. Bungalows would give way to mansions, mansions to burned-out lots, and at every gas station, panhandlers waited in search of change. I asked Black if he, or his brethren, thought of the South Side as a ghetto, and he shook his head, noting that it had always been filled with people like him and his parents, people who worked.
Like its New York counterparts—Harlem in Manhattan, Jamaica in Queens, and Bedford-Stuyvesant in Brooklyn—the South Side is a black island in a mostly white city. But if the South Side were an island, it would be huge. Unlike Harlem, the South Side isn’t one neighborhood, but a collection of smaller neighborhoods covering 60 percent of the city. All told, the sprawling South Side is arguably the country’s largest black enclave.
We stopped for lunch at Pearl’s Place, a homey southern restaurant on South Michigan Avenue. We ate chicken, and Black broke down the South Side’s place in black American lore with unabashed pride. “We were always entrepreneurial types,” he explained. “We couldn’t yell for taxis. They wouldn’t come into the black community. So we created taxi companies. The concept of the jitney was created in Chicago. You couldn’t afford to die, because white mortuaries wouldn’t bury you. So we did it ourselves. We made places like this—places to eat. A single man could come up from the South and get good home cooking and companionship.”
Black’s memories of Chicago strivers draw from a deep well of myth and fact. The black power struggle in Chicago literally dates back to the city’s founding by the 18th-century trader Jean Baptist Point Du Sable, who, like the president-elect, was a biracial black man. The South Side has been home to the largest black insurance companies in the North, such as Supreme Liberty Life and Chicago Metropolitan Assurance. Ditto for black banks like Seaway National and Independence. Half of the first 14 black CPAs came out of Chicago. The publications that defined black Americans—the Chicago Defender, Ebony, and Jet—were also products of Chicago.
The first black congressmen elected in the 20th century were South Siders Oscar De Priest and his successor Arthur Mitchell. For years, they were the only black congressmen. The only two serious African American presidential campaigns—those of Jesse Jackson and Barack Obama—came out of the South Side. Indeed, Barack Obama, Louis Farrakhan, and Jesse Jackson all lived or worked within a 10-minute drive of each other.
Chicago in the early 20th century was racist and segregated, but whereas in the South black voters were violently suppressed, in the North they were encouraged—the better to feed Chicago’s infamous machine. Moreover, Chicago’s industry was booming, and the Defender painted the city to southerners in typical immigrant fashion—streets paved with gold, and jobs for all who wanted them. For years, the saying among Timuel Black’s peers was a reverse of the old Frank Sinatra riff—“If you can’t make it in Chicago,” they’d say, “you can’t make it anywhere.”
That promise of a better life drew Michelle Obama’s grandparents out of the South and into Chicago. Within Chicago’s Black Belt—a network of neighborhoods kept segregated by Chicago’s restrictive housing covenants—was the sort of oppressive poverty that spawned terms like the underclass. And yet, alongside this privation was a proto-middle-class group of blacks who held the community together. Obama’s mother, Marian Robinson, came up among them.
“Most of the people were working government jobs, like the post office. My father was a decorator. There was a gentleman in our neighborhood who owned a grocery store,” Robinson recalled. He “had to go to his farm to pick up his groceries. It was rough. There were plenty of reasons why people could not do. People who couldn’t afford rent for a whole apartment, they would share.”
But the hardship forged values in Robinson that she passed on to her kids. “That’s where we got our understanding that it was going to be hard, but you just had to do whatever it takes,” she said. “We all went to church. I was a Brownie. I was a Girl Scout. We all took piano lessons. We had drama classes. They took you to the museum, the Art Institute. They did all those things, but I don’t know how. I grew up with a grandmother and an aunt. My aunt would do things my mother would not or could not.”