Hanging around Santita’s house could be exciting. The place was roomy and a little chaotic, home to the family’s five children and stuffed with heavy Victorian furniture and antique glassware that Santita’s mom, Jacqueline, liked to collect. Mrs. Jackson, as I called her, had an expansive spirit and a big laugh. She wore colorful, billowy clothes and served meals at a massive table in the dining room, hosting anyone who turned up, mostly people who belonged to what she called “the movement.” This included business leaders, politicians, and poets, plus a coterie of famous people, from singers to athletes.
When Reverend Jackson was at home, a different energy pulsed through the house. Routines were cast aside; dinner conversations lasted late into the night. Advisers came and went. Plans were always being made. Unlike at my apartment on Euclid, where life ran at an orderly and predictable pace, where my parents’ concerns rarely extended beyond keeping our family happy and on track for success, the Jacksons seemed caught up in something larger, messier, and seemingly more impactful. Their engagement was outward; their community was big, their mission important. Santita and her siblings were being raised to be politically active. They knew how and what to boycott. They marched for their father’s causes. They went on his work trips, visiting places like Israel and Cuba, New York and Atlanta. They’d stood on stages in front of big crowds and were learning to absorb the anxiety and controversy that came with having a father, maybe especially a black father, in public life. Reverend Jackson had bodyguards—large, silent men who traveled with him. At the time, it only half registered with me that there had been threats against his life.
Santita adored her father and was proud of his work, but she was also trying to live her own life. She and I were all for strengthening the character of black youth across America, but we also needed rather desperately to get to Water Tower Place before the K-Swiss sneaker sale ended. We often found ourselves looking for rides or to borrow a car. Because I lived in a one-car family with two working parents, the odds were usually better at the Jacksons’ house, where Mrs. Jackson had both a wood-paneled station wagon and a little sports car. Sometimes we’d hitch rides with the various staff members or visitors who buzzed in and out. What we sacrificed was control. This would become one of my early, unwitting lessons about life in politics: Schedules and plans never seemed to stick. Even standing on the far edge of the vortex, you still felt its spin. Santita and I were often stuck waiting out some delay that related to her father—a meeting that was running long or a plane that was still circling the airport—or detouring through a series of last-minute stops. We’d think we were getting a ride home from school or going to the mall, but instead we’d end up at a political rally on the West Side or stranded for hours at the Operation PUSH headquarters in Hyde Park.
One day we found ourselves marching with a crowd of Jesse Jackson supporters in the Bud Billiken Day Parade. The parade, named for a fictional character from a long-ago newspaper column, is one of the South Side’s grandest traditions, held every August—an extravaganza of marching bands and floats that runs for almost two miles along Martin Luther King Jr. Drive, through the heart of the African American neighborhood that was once referred to as the Black Belt but was later rechristened Bronzeville. The Bud Billiken Day Parade had been going on since 1929, and it was all about African American pride. If you were any sort of community leader or politician, it was—and still is, to this day—more or less mandatory that you show up and walk the route.
I didn’t know it at the time, but the vortex around Santita’s father was starting to spin faster. Jesse Jackson was a few years from formally launching a run to be president of the United States, which means he was likely beginning to actively consider the idea during the time we were in high school. Money had to be raised. Connections needed to be made. Running for president, I understand now, is an all-consuming, full-body effort for every person involved, and good campaigns tend to involve a stage-setting, groundwork-laying preamble, which can add whole years to the effort. Setting his sights on the 1984 election, Jesse Jackson would become the second African American ever to run a serious national campaign for the presidency, after Congresswoman Shirley Chisholm’s unsuccessful run in 1972. My guess is that at least some of this was on his mind at the time of the parade.
What I knew was that I personally didn’t love the feeling of being out there, thrust under a baking sun amid balloons and bullhorns, amid trombones and throngs of cheering people. The fanfare was fun and even intoxicating, but there was something about it, and about politics in general, that made me queasy. For one thing, I was someone who liked things to be neat and planned in advance, and from what I could tell, there seemed to be nothing especially neat about a life in politics. The parade had not been part of my plan. As I remember it, Santita and I hadn’t intended on joining at all. We’d been conscripted at the last minute, maybe by her mother or father, or by someone else in the movement who’d caught us before we could follow through on whatever ideas we’d had for ourselves that day. But I loved Santita dearly, and I was also a polite kid who for the most part went along with what adults told me to do, and so I’d done it. I’d plunged myself deep into the hot, spinning noisiness of the Bud Billiken Day Parade.
I arrived home at Euclid Avenue that evening to find my mother laughing.
“I just saw you on TV,” she said.
She’d been watching the news and spotted me marching alongside Santita, waving and smiling and going along. What made her laugh, I’d guess, is that she also picked up on the queasiness—the fact that maybe I’d been caught up in something I’d rather not do.
* * *
When it came time to look at colleges, Santita and I both were interested in schools on the East Coast. She went to check out Harvard but was disheartened when an admissions officer pointedly harassed her about her father’s politics, when all she wanted was to be taken on her own terms. I spent a weekend visiting Craig at Princeton, where he seemed to have slipped into a productive rhythm of playing basketball, taking classes, and hanging out at a campus center designed for minority students. The campus was large and pretty—an Ivy League school covered with ivy—and Craig’s friends seemed nice enough. I didn’t overthink it from there. No one in my immediate family had much in the way of direct experience with college, so there was little, anyway, to debate or explore. As had always been the case, I figured that whatever Craig liked, I would like, too, and that whatever he could accomplish, I could as well. And with that, Princeton became my top choice for school.
Early in my senior year at Whitney Young, I went for an obligatory first appointment with the school college counselor to whom I’d been assigned.
I can’t tell you much about the counselor, because I deliberately and almost instantly blotted this experience out. I don’t remember her age or race or how she happened to look at me that day when I turned up in her office doorway, full of pride at the fact that I was on track to graduate in the top 10 percent of my class at Whitney Young, that I’d been elected treasurer of the senior class, made the National Honor Society, and managed to vanquish pretty much every doubt I’d arrived with as a nervous ninth grader. I don’t remember whether she inspected my transcript before or after I announced my interest in joining my brother at Princeton the following fall.