by Kent Jacobson
For my son, Morgen
I remember Roone from the first night, the way he leaned in too close in prison blues, the hulking linebacker build, his eyes a blank: “You too pretty to survive in here.” He delivered a sweet to me, the new guy.
So this is what it’s like, I thought. Men will threaten me, study my collapsing face, and walk off. I’m another fool to prey on.
Minutes before, I’d set off the metal detector barely inside the outer gate. “Got more than papers in there?” A grim guard stuck out his hand to gesture for my messenger bag, my butt up against a metal handrail in a tight corridor. Other guards watched from behind a black-green window of bulletproof glass as grim guard’s hairy hand groped through my bag. He pulled out pens, papers, a book, an orange, a half-empty jar of Mentholatum, a worn eelskin wallet that had been a gift from my wife, three pennies, and⸻a metal fork from that day’s lunch.
“That’s a weapon,” he said, and tossed the fork onto a nearby desk. His jaw tightened. “These guys are in here for a reason, professor. Not because they’re nice.” Innocents like me made his job harder.
It was 1990 and there was state and federal money in Connecticut for prisoners to pursue a college degree. At forty-six and after years of college teaching, I made films for environmental groups. Days had become a slog of letters written to potential clients, sample reels sent, cold calls, and rare face-to-face meetings. I felt desperate.
Then a poet at the community college phoned to say he had work. Was I interested in a part-time spot as an English teacher in a prison? I laughed. “Me? Why do that?” Sixty days later I walked into Roone’s prison.
“Stand against that wall.” One more guard, his pants tucked into high black boots, snapped pictures, front and both profiles, and handed me a Release Form⸻“Fill out and sign it”⸻which freed the prison from responsibility after I got taken hostage.
“Let’s go.” Black Boots led me outside to M-building which was a cramped cage of steel doors and concrete and voices blasting off walls. Fifty or sixty men in blue denim feasted on the dude in herringbone and Fratelli Rosetti shoes.
I heard “. . . choirboy . . . what’s he doin’ . . . ?”
I followed the guard’s back to a tiny room with no windows, a minuscule blackboard, and a dozen desks too small for grown men. They trailed in. A thirty-year-old with a massive chest and huge hands approached.
“Roone, James Roone. I’m on your list. Look it up.”
“You’re fine,” I said with an edge. “Have a seat.” That’s a mistake. I can’t out-tough them.
Roone rocked side to side⸻one foot, the other⸻his eyes shifting and never settling. He bent closer and I smelled peppermint. “You too pretty to survive in here.”
Someone chuckled from the door.
According to my poet friend Alex who recommended the job, “Roone’s a pimp and they’re the worst.” He shook his head. “They’re loners; they don’t want friends.”
Roone liked to intimidate; the “you too pretty” introduction said that.
A story circulated about a young guy who assaulted one of Roone’s “girls” and landed in the same prison with Roone. Prison code demanded the pimp retaliate, so he offered the 130-pound assailant a seat in a card game. Because he feared worse, the guy agreed and saw Roone was cheating and, despite the knowledge, continued to play⸻and pay. Pimps crave control, Alex said. I tried not to think what Roone might do in my literature classroom.
I’d taken the prison work because I needed to feel useful. And for sure, I was curious. I’d grown up around hard men, my father the first. Raised poor in a city slum, he warred like the underdog he realized he was. He drank with a mob gangster and directed a state agency. He understood a hard world. I loved him. He nicknamed me “Butch” as a baby because I sweated so much when I nursed. I was do-or-die like him though he worried literary me would be “too soft” for this world.
I loved him for his unbending endurance, his persistence against the odds, the more impossible the task the better. After work and on weekends he nearly singlehandedly transformed a twenty-five-room architectural relic into a summer inn, so there’d be money for us kids for college, money his own father had refused him. “Life has to be about more than yourself,” he said. You need “good work.” You have to serve.
He died younger than he should have and I hardly knew him. He eluded me behind his wall of anger and alcohol, his rages scary. We didn’t share a searching, unguarded word between us. Said bluntly, I think I went to a prison to find him, to glance behind the tough masks men like Dad wore. That sounds dumb. Fine. I said it.
A college official warned me. “No sensitive subjects in prison. Don’t get personal. They won’t drop their defenses and bare wounds. They don’t trust the guards, they don’t trust inmates.” They don’t trust you, he implied. He seemed anxious about what I’d set off if discussions ran too deep. Caution was best.
I imagined prisoners preferred any college class over surly guards, mess-hall food, screeching TVs, and brawls. A degree brought status, a way to certify⸻to guards, the warden, a counselor, the parole board, abandoned children, an ex-wife, perhaps the man himself⸻that he trudged a better road. Still, I wasn’t sure what to do with the official’s push for caution.
I picked stories I considered readable like Washington Irving. Discussions were bumpy but not explosive, their bumpiness a result, I suspected, of my early-session jitters. And yes I picked stories to nip at problems that might be grinding in the men: the plight of the outcast in “Rip Van Winkle”; cynicism in Nathaniel Hawthorne. I hadn’t been practicing what the official urged and I should comply if I hoped to keep teaching.
Even so, I wasn’t hearing appeals for caution from the men (Roone kept to himself). Talk straight, they insisted, talk straight. We discussed “Young Goodman Brown,” a Hawthorne story in which an uncommonly tender-hearted Puritan discovers his wife and the town’s elders among a forest congregation of Devil-worshippers. Brown turns distrustful and retreats from everyone. One man asked, “You cynical like Goodman Brown, Dr. J? You think that’s right? You do that?” He was asking for advice.
They were serious about right and wrong and I hadn’t expected that. They appeared in search of . . . call it personhood⸻What kind of man am I really?⸻in an institution (and society) that hosed them with disrespect (“These guys are in here for a reason . . . . Not because they’re nice”). They took courses to untangle their lives, to see themselves in a more complicated light, to discover in the prison darkness who at heart they were. Or so I sensed.
I began the analytic writing part according to convention⸻with lessons on topic sentences and paragraphs⸻and got another surprise. I’d expected prisoners to be different than me, more strange than familiar, possibly inscrutable. Then their lives streamed into the prose . . .
One man with dyslexia described the primary-school teacher who said he was “slow” and the kids who called him “a moron.” A second man touched on childhood with his mother after his father, whom the writer strongly resembled, left the family. His mother lashed out with little reason at her child, the writer⸻“You make me sick. I can’t stand you.” He wrote now, “Why does she hate me?”
These were typical, except for those like Roone whose language was non-specific befitting many green writers. I hadn’t requested an autobiography and here it was. They need to reflect on their lives, I thought. Maybe I should reduce the emphasis on mechanics. The writers come mainly from sinking cities and defeated schools, their training in English pretty thin. Stress mechanics and I’ll likely freeze the prose. Who learns to write by recognizing run-ons? I want to get them more genuinely on the page in their own voice, which isn’t English perfect. I’ll let the men walk their thorny pasts and see what happens. Won’t they learn faster writing through experiences that haunt them?
The stories, though not from Roone and a few resistors, rushed out. An adolescent, addled on drugs, killed a policeman. A small boy watched a stepfather beat the boy’s mother⸻the shredded blouse, the bloodied mouth, the broken teeth, the shame of the boy’s helplessness. A third detailed a prison visit:
There she is, sitting . . . in the middle row of tables that line the brightly lit room. She is looking around anxiously, trying hard to keep her composure. . . . As I stare through the wire-glass window, waiting to enter the room, I hear the metallic click of the lock. The door pops open, and I walk through. The moment I enter, my eyes fix on my mother’s. Her hand flies up to her face and covers her mouth with such pressure that her fingers turn white. I can see the pools of tears well up in her eyes as I approach the table.
“Oh, I’m sorry. I didn’t want to do this,” she tells me as I sit down.
I reach across the table and grab her hands. I can’t speak. All that I keep thinking is, why is she still apologizing to me?
They probed their lives, so I prodded. I nudged, I questioned, I listened, I tried to understand. “Don’t believe anybody who says writing isn’t personal,” I said. “It takes courage to face dragons.” I urged them to shape stories on a mentor, a neighborhood legend, growing up fast, the right thing. In no time, although this hadn’t been my intention, I became the character who taught autobiography. The writing burned, the most alive I’d read in student papers. I got inside hard men, men I saw both in and outside of prison.
I compiled Rules for the Writing Road and passed them out: maxims styled by professionals (Gene Fowler: “Writing is easy. All you do is stare at a blank sheet of paper until the drops of blood form on your forehead”); and maxims styled by the men (“Hit the reader between the eyes with a 2 by 4”).
I realize I was pushy. Must be writing a book, they joked. “This is college,” I told them. “Expect to be pushed. Expect to learn things that may be painful, but you’ll thank God you learned them. Forget the usual English paper. Tell stories, be a storyteller. Plow your past.”
Several like Roone continued to write distantly, while others loudly resisted the class’s direction. Weeks in, one man responded to a prompt: “Great, another fucking book writer. I’m not too fond of people who ask a lot of questions. You never know what they’re up to.” A second wrote, “Another person wants to invade my mind. My private struggle. One that I try to bury every night of my life. This person, this, this college teacher, Mr. Do-Good, he wants to invade my private world, my private fight.” I was an intruder.
To a third I was a “bleeding heart . . . liberal-minded BMW driver that wants to reform us.” I drove a Toyota. Even so the writer was right that I grasped a minimum. What did I know about poverty, or parents who bolted, or the view from the bottom? I was another nosy social worker to him in a lifetime of nosy social workers. Telling his stories stripped his armor and made him “prey for prison predators.” Any show of hurt⸻any sorrow, any whisper of insecurity or fear⸻stole his protection.
No teacher wins them all, I told myself. What did I expect . . . . I sympathized with the resistance. How many of us can stand to look at our lives? Who welcomes getting bloodied by bull-briars from poking around in bushes? Like Eliot claims in Four Quartets, “Human kind cannot bear very much reality.” Who welcomes too much reality?
Roone expressed no clear resistance to storytelling and yet his writing resembled what one inmate branded “plastic fruit”⸻“There’s nothing to taste, smell, or touch.” Roone appeared to learn a minimum from me or the writers we workshopped.
Then the semester ended and there was his evaluation. He wrote “in generalities,” he said, “to prevent exposure of my personal life.” What had he expected from the course? “3 credits with a high grade.” His major criticism? “None.” Major positive? “I learned.”
I was sure I wouldn’t see him again as a student.
Two years later and I was running a course on popular culture, memoir-writing standard whenever I taught in the prison. I’d won the cautious official and drew men now who had to write on their lives.
The opening class, Roone sat spread-eagled in one of the tiny desks⸻“Hey, Teach”⸻a big smile.
I pretended I wasn’t surprised although each time I’d seen him since our earliest encounter, I got the same dismissive “Hey, Teach.” I was the professor the rock-hard avoided, the ones who refused to open in their writing. Roone I considered rock-hard. I couldn’t get why he was here.
Several weeks flew by. Roone was restrained and agreeable, even polite.
Then he lost control. He raged in every session and I wish I understood why. I don’t remember the words, only the decibels. He raged from his chair about Tobias Wolff’s This Boy’s Life, about Babe Ruth, about an assembly line in an automobile factory. His eyes danced, fingers pointed, arms waved, his actions so inflated I wondered what triggered them. A prison threat?
Roone’s bullhorn voice silenced the room. “I’m about fire and ice,” he wrote to me in a note, “not bubble bath.” I’d pick a thread from one of the harangues and try to redirect. Men ducked their heads and studied a page in the story. I had to be careful. I shouldn’t embarrass him in front of the group. That would make me his enemy.
The thrashing played like a blind attempt to cow us all, to drive everyone away, an animal default that worked. And for what? An illusion of safety? He was a bully (“a crazy bastard,” one man labelled him in private)⸻cocksure, obnoxious, mistrustful, and (most important) profoundly alone. The men reacted as most of us do if a person isn’t easy. “Guy’s weird,” we say, and retreat.
I went for help to the college dean whom I knew slightly. We’d gone to graduate school together. What were my options? Could I bounce Roone? Would the dean back me?
No. Dismissal was out. The college “doesn’t want trouble with Corrections.” The dean wasn’t precise on the “trouble.” “Situations like these can get messy.”
“Why not reason with the guy?” he said.
I thought, Sure, you try. Roone’s blasts, the detached writing, our patchy conversations, they hinted Roone wouldn’t confess what bothered him even if he knew.
Early next morning, coffee-cup in hand and alone at the kitchen table, I pondered what he’d do if I confronted him.
He’d hammer me.
They’d haul him to isolation, he’d lose privileges, jeopardize his parole, and probably serve a longer sentence. He’d self-destruct. And yet his rages were self-destructive. They made him enemies. I really had almost no idea what he’d do.
And I worried I’d lose this very part-time, underpaid job if I didn’t fix this mess. Two years earlier when I started in the prison a woman asked me why, why go there? And without thinking I said, “Because sometimes I get glimpses of the boys they were.” Like that should answer her. Teaching in prison unwrapped hard men and, as strange as it sounds, the experience settled me, the world quieted. The “boys” I met weren’t frightening. They were me, like us all, hurt and struggling to keep on: against helplessness and regret, distrust and imperfect parents and self-harm. Up against it like the rest of us.
We’re outcasts and underdogs at our saddest moments, feeling abandoned and wondering what we’d done to be this alone, locked in our own mess, hurt and wounded and burning for another life. What did we do? “We’ve all been down the same road,” a man declared in class one night. We’re all (his words) “trying to crawl out of a shithole.”
The curtain had begun to lift on Dad. He had suffered⸻from the infant polio which forced an athletic man to lurch with a limp, and from a father who deserted him emotionally right to the end. The morning Grampa put a bullet into his own brain, Dad drank whiskeys and drove the new pastor right out the front door: “What’s that young punk understand about any of this?” What did I?
No one’s life is easy; being human is impossibly difficult. These men (and the “boys” they’d been) cemented that fact. I’d supposed Dad’s hardness had been a solution to life, that hard men didn’t suffer like the rest of us, that a muscled attitude got them through. And the prison writing said no, no way, it wasn’t true.
In spite of that, maybe not so oddly, I still clutched notions about the men, about men like them. They’re beasts. They have no inner life worth a mention. I branded Roone a thug which was, I think, the way he wished to be imagined. I didn’t see past his bulk, the swagger, the threat of violence. He didn’t reveal himself.
I remembered what one man said. “When Roone talks to convicts, he rarely looks them in the eye. His eyes dart, his eyes dart, they go places.” I missed what the darting eyes said: Roone wasn’t fully present, ghosts stalked him. Behind the eyes was likely a boy, orphaned and brutalized, a boy cramped with fear, a boy the grown pimp had to protect from further harm and in whose defense he had doled out plenty.
I didn’t see the boy. Roone scared me. I was flailing to end a problem in a classroom.
I caught him in the hall next week and motioned him into an alcove. We had to speak without onlookers. A poster read, “60% of America’s rapists, 72% of adolescent murderers, and 70% of long-term prison inmates grew up without fathers. Cambridge Research Group.”
I searched Roone’s face. “You take up too much room, James. Things have to change.”
He edged nearer. I hadn’t used his first name before.
“I’ll give you two choices,” I said. “You can drop and that will be that. I won’t say a word to the prison or the college. This is between you and me.”
His face said nothing. I was convinced the course didn’t mean that much to him. Prison blue rushed by, feet away.
“Or”⸻I was afraid of what I’d say next⸻“you can do the reading, write the papers, meet all the requirements, but . . . ,” I took a breath, “you have to keep quiet for the rest of the semester. No talking in class.”
“What the fuck?” He backed up, head to a side, and glared down at me.
A guard stood barely out of view. The men claimed guards “give no respect.” If one stepped in, I’d become them. I’d lose Roone and the trust of the rest. I’d have to quit.
Roone said nothing.
“It’s your choice. Think about it. Next week you can tell me what you decide.”
He turned, mumbling, and I followed him to Classroom 3. I had no confidence I’d get through the next two-and-a-half hours.
Roone might complain to prison staff. He might go to inmates and gripe that I quashed him. He’d stomp to the dean who’d vetoed his dismissal and say the silence I required was just that, dismissal.
Monday, I maneuvered past the guards to M-building. There he was, alone, in the hall with his notebook. The two of us retreated into the alcove where we had spoken a week ago. He appeared calm without the usual “Hey, Teach” or the rocking side to side. He stepped just close enough, his eyes unexpectedly still.
“I won’t quit,” he said, glancing left and back to me. His shoulders relaxed and he spoke softly, nearly a whisper. “I can’t. I need this.”
I didn’t understand. He knew the course wasn’t required. He didn’t need it for the parole board; he had plenty of credits. Men had the right to drop without penalty.
“I won’t drop. I want this. I have to finish.”
I nodded like I understood. He left me in the alcove and strolled across the hall as if we’d been merely passing time.
Friends puzzle over why Roone stayed, and I have no certain answer. A man who trusted no one seems to have trusted me . . . a little. I was an innocent who listened, however small my understanding. He sensed my ease with underdogs. Or maybe the dark reality of others’ prose held him. Or, maybe, unlikely as it seems to me now, these thirty years later, Roone saw a chance to stare down the dragons that shadowed him.
He attended every session and I realized he hadn’t missed one, in either course. He submitted the writing, always on deadline, and the writing thickened. Yet he avoided his childhood, his crimes, his aching. He was tied up, and might, like Dad, never come loose.
I imagined a father who left and a mother who betrayed him, although his eyes said worse. And still I didn’t know. He may have feared the tiny boy he had been, and had to look away, even if he had tried not to: “I want this. I have to finish.”
He did finish and never spoke again. He likely assumed dropping would bring him nothing good. An administrator, me, an inmate, a guard⸻one would get him somehow and pull apart his plan to complete the bid and go home. He could control his talk when it mattered, but not what they might do.
Kent Jacobson has taught for nearly thirty years in prisons and one Massachusetts inner-city. His nonfiction appears in The Dewdrop, Hobart, Talking Writing, Lucky Jefferson, Punctuate, Under the Sun, and elsewhere. He can be reached at email@example.com.