I grew up in one of Chicago’s most prestigious, most progressive, most expensive private schools. I arrived as a precocious almost-four-year-old for preschool (what we called “junior kindergarten”) and left at 17 with a high school diploma and the best education that money could buy.
Remembering the freedom we had to run amok in those days is both hilarious and terrifying. We were allowed to “sign out” during free periods starting in eighth grade, which meant that at any given time a good chunk of the student body aged 13-18 was roaming the streets of the north side of Chicago, like feral cats, with Sony Walkmen and Marlboro Lights and extremely questionable judgement in hand. Our thrice-weekly assemblies, called “Morning Ex” in homage to the “morning exercises” of the school’s storied past, were largely student-planned, so the guest speakers brought in were occasionally eye-opening beyond what may have been entirely appropriate. My senior year, our class t-shirt was a celebration of the traditional senior hot-dog booth at the all-school county fair in the fall: the front of the shirt was a cartoon of Sleeping Beauty, napping, with the Prince looking down at her questioningly and the words WHEN A KISS WON’T DO… underneath; the back of the shirt featured a wide-awake Sleeping Beauty holding a up a hot dog with a huge smile on her face and the suggestion TRY A SENIOR WEINER! underneath. I have no recollection of any adult—a teacher, administrator, or parent—ever saying or doing anything about this shirt except shaking their head. I wore mine until it disintegrated, sometime in college.
The school was, it goes without saying, extremely wealthy and extremely white, and most of us were, it also goes without saying, absolutely marinated in privilege, with the extra layer of smugness that goes along with being “progressive.”
All of this is context for the prank executed by the senior class, bless their hearts, in the spring of my sophomore year. This was a senior class with a capital-R Reputation for drinking, drugging, and general rule-breaking of all kinds even beyond the normal anarchy that was table stakes in the eighties (although reasonable people can disagree on how much of the Reputation was based in reality and how much was carefully curated adolescent blather). The ringleaders of the class were a group of boys with enormous amounts of money and a corresponding lack of sense who seemed—at least from my sophomoric, wide-eyed perspective—all-powerful and untouchable.
The Morning Ex at which the prank took place began like all the others. We shuffled into the auditorium, which had the school motto (“A School Should Be A Model Home, A Complete Community, An Embryonic Democracy”) in big letters across the proscenium, at 10:50 a.m. (To this day, I will sometimes have an OH SHIT MORNING EX moment when the hands of a clock are on the ten and almost-eleven.) People lined up at the front to make various announcements about play rehearsal and the bake sale and prom tickets. We ignored them and talked to our friends and were shushed.
Suddenly there was a commotion in the senior section, which was in the back right of the auditorium. The sophomores sat in the front, so we all twisted around to see what was going on. A small knot of burly men in suits—one had a dark mustache and a brown check suit, a weird detail that I remember vividly—were stomping down the aisle waving badges and yelling about drug busts and pushing their way into the senior seats. As we all sat there gaping, they grabbed three of the Ringleader Boys of Great Wealth and Little Sense, pulled them to their feet, handcuffed them, and marched them out of the seats, back up the aisle, and out the back door of the auditorium.
It was pandemonium. The seniors were screaming and waving their arms—an Oscar-winning performance, really, since they all must have been in on it. A girl in my class, who was dating one of the handcuffed boys, was crying hysterically, almost hyperventilating. To this day, I don’t know if she was acting or was truly surprised (and traumatized). The rest of us melted down completely. I have no memory of the logistics of what happened next, but at some point it became clear that the “arrest” was a joke; the class had flawlessly choreographed and performed a law-enforcement-flavored flashmob as their senior prank. I do have a vague recollection of all of us tumbling out of the auditorium into the hallway and seeing the three boys standing there laughing and shaking hands with the burly men, off-duty CPD detectives who had done it as a favor for one of their dads, a well-known local attorney.
The whole thing was considered a smashing success, so extremely clever and well-planned, the best senior prank in memory, maybe ever.
I made wonderful, lifelong friends at my school. I had wonderful, brilliant teachers, several of whom remained so important to me as an adult that they were guests at my wedding. And I learned a lot, a lot that was good and important. I learned how to write with clarity, how to read with curiosity, how to speak with confidence, how to think critically. I learned a lot about (white, western) literature and history and art and music and theater. I was at the time and remain to this day very aware of how lucky I was, and I’m enormously grateful in many, many ways.
I also learned a lot of lessons that I wasn’t aware I was learning at the time and have a hard time facing even now, lessons that have colored my view of the world just as much as my (white, western) literature and history classes. Those lessons, the ones about privilege and power and race and class and law enforcement and accountability and smugness and “progressive” education and politics, are part of a system—a centuries-old system that was the oxygen of the rarefied air we breathed but never acknowledged at my school at that time. But I do understand, now, that it’s a system that I’m a participant in, and a perpetuator of, and those are the lessons that I will spend the rest of my life unlearning.


The question is do you remember when they mural was painted in the green and white generic display?
Loved your post. Following in the steps of Jesse. Just donated his high school diploma to the archives. Keep,them coming