Glenwood School for Boys and the Journey from Rejection to Prison
I got sent to Glenwood School for Boys the same year the German submarine U-505 rolled up to the Museum of Science and Industry. I grew up at 62nd and Dorchester on Chicago’s South Side—close enough that the museum was practically home turf. Everyone was talking about the submarine. But I wasn’t there to see it. I was already gone.
Out of four kids, I was the one sent away. My older sister had been left on the doorstep of Lutheran General Services shortly after she was born. You’d think my parents would’ve figured out then that maybe they weren’t cut out for raising children. But no. They kept trying. And when it came time to thin the load, I was the one they chose.
Glenwood wasn’t all bad. It wasn’t all good, either. I was small, quiet, the second son of an abusive, alcoholic bartender. At home I’d already learned that shoes were meant to be thrown, words meant to wound. At Glenwood, I learned something else—that if you bury yourself in books and schoolwork, you can almost disappear. That’s what I did my first year.
Then came Flag Day, 1955.
They called out a name—“Private Jonathan Thomson.” Boys looked around, whispering. “That’s you, they mean you.” My name wasn’t Jonathan. But on my first day, a captain had decided it was. So that’s what stuck.
I walked stiffly forward, confused, until they handed me a medal. Later I learned it was for the top grades in the entire school. I was twelve years old, standing on a stage under a name that wasn’t mine, holding a medal I didn’t know I’d earned. And in the audience, for the first time in nine months, sat my mother. Her first visit. Watching me succeed from a distance.
That was Glenwood in a nutshell: success with a false name, achievement mixed with rejection.
I did find things to cling to there. I loved marching. The rhythm, the loyalty, the sense of belonging to something bigger. I hated cruel authority, but I loved discipline. By my last two years, our company was winning the Flag Day marching competition, and I was leading the second column.
But popularity? Never. I wasn’t an athlete. I wasn’t the boy with a dad in the stands. My dad didn’t play catch. He hurled shoes.
The summer of ’56 at Camp Glenwood lit the match. The counselors that year were mean, and rebellion was in the air. A bunch of us hatched a plan—escape across the lake. We stole life preservers, swam across, thought we’d made it. But waiting for us on the other side were the men we thought we’d left behind. They marched us all the way back.
That was my first real taste of rebellion. After that, the fuse inside me was burning.
The next year I went to an eye doctor in Homewood. Instead of waiting for the return car, I wandered off. Blurred vision, walking aimlessly, I wound up in Hazelcrest. A man called my name. I thought he was a family friend. Turns out, he was my mother’s new husband. News to me.
I hadn’t even known she’d remarried. Hadn’t known she lived just down the road. For years, I’d believed I was at Glenwood because “we can’t afford you.” But now I knew. She had a new family. I wasn’t part of it.
By 1957, my siblings were home. I wasn’t. And bitterness became my closest companion.
Seventh and eighth grade blurred through three Catholic schools. I never finished grade school. At thirteen, I was already on juvenile parole for stealing cars.
The first one was almost an accident. A man delivering furniture asked for directions. I climbed in to help. When he left the car running, I slid behind the wheel and drove off. The furniture went flying out the back. I just kept driving.
It became a habit. Every time anger welled up, I stole a car.
And sure enough, I climbed the ladder of the justice system one rung at a time: St. Charles. Sheridan. Ashland. Kentucky. El Reno, Oklahoma. Each stop another lesson in how to be hardened.
When I was eight, after being caught shoplifting, my mother had told me: “You keep on like this and you’ll end up just like your father. You’ll be in prison before you’re twenty-one.”
She was right.
I entered Marion Federal Penitentiary just months before my twenty-first birthday. Marion was built to replace Alcatraz, and by the time I walked in, the older cons from the Rock were long gone. In their place was a younger, tougher, more reckless crew. I was one of them.
Seventeen and a half years of my next two decades would be served behind bars. What started with cars ended with armed robbery. In July of 1971, at age twenty-six, I robbed a bank in St. Louis. I was already worn out. I resigned myself to prison for life.
That’s the journey Glenwood helped set in motion.
Glenwood gave me pride in books and medals. It gave me structure, loyalty, and marching drills. But it also gave me bitterness, rebellion, and the cold realization that rejection was my inheritance.
That was my Glenwood School for Boys. And that was my road from rejection to prison.
Thomson's Home Emporium 