In the manner of all high schoolers everywhere, my friends and I liked to

loiter. We loitered boisterously and we loitered in public. On days when school
got out early or when homework was light, we flocked from Whitney Young to
downtown Chicago, landing in the eight-story mall at Water Tower Place. Once
there, we rode the escalators up and down, spent our money on gourmet
popcorn from Garrett’s, and commandeered tables at McDonald’s for more hours
than was reasonable, given how little food we ordered. We browsed the designer
jeans and the purses at Marshall Field’s, often surreptitiously tailed by security
guards who didn’t like the look of us. Sometimes we went to a movie.

We were happy—happy with our freedom, happy with one another, happy
with the way the city seemed to glitter more on days when we weren’t thinking
about school. We were city kids learning how to range.

I spent a lot of my time with a classmate named Santita Jackson, who in the
mornings boarded the Jeffery bus a few stops after I did and who became one of
my best friends in high school. Santita had beautiful dark eyes, full cheeks, and
the bearing of a wise woman, even at sixteen. At school, she was one of those
kids who signed up for every AP class available and seemed to ace them all. She
wore skirts when everyone else wore jeans and had a singing voice so clear and
powerful that she’d end up touring years later as a backup singer for Roberta
Flack. She was also deep. It’s what I loved most about Santita. Like me, she could
be frivolous and goofy when we were with a larger group, but on our own we’d
get ponderous and intense, two girl-philosophers together trying to sort out life’s
issues, big and small. We passed hours sprawled on the floor of Santita’s room on
the second floor of her family’s white Tudor house in Jackson Park Highlands, a
more affluent section of South Shore, talking about things that irked us and
where our lives were headed and what we did and didn’t understand about the
world. As a friend, she was a good listener and insightful, and I tried to be the
same.

Santita’s father was famous. This was the primary, impossible-to-get-around
fact of her life. She was the eldest child of the Reverend Jesse Jackson, the
firebrand Baptist preacher and increasingly powerful political leader. Jackson had
worked closely with Martin Luther King Jr. and risen to national prominence
himself in the early 1970s as the founder of a political organization called
Operation PUSH, which advocated for the rights of underserved African
Americans. By the time we were in high school, he’d become an outright
celebrity—charismatic, well connected, and constantly on the move. He toured