The Perfect Prison

When I was twenty-three, I found myself unemployed, and living in my girlfriend’s room in her parents’ beautiful brick house on the South Side of Chicago in an affluent white neighborhood slipping into descent after the M.L.K. riots of 1968. They kept me upstairs and visible, with girlfriend relegated to the basement.

Chicago during 1968 M.L.K. riots.
Chicago, summer of 1968.

I remember wandering the streets day-after-day-week-after-week begging for work, sliding in and out of tawdry bars – sticky-floor flyblown dives I’d never venture into for a drink on my own – but places I now prayed would hire me because I’d just spent my last $250 attending “Professional Bartender’s School” and earning a “Professional Bartender’s Certificate” after spending a week pouring colored water out of fake liquor bottles into appropriate glasses.

Armed with this “certificate”, I wandered into dozens of Chicagoland watering holes, but no one would hire me. Sheila’s Puke Shack owner S. Hardnutter threw me the stink eye when I dangled the Professional Bartender Certificate in front of her narrow eyes, then pointed toward the door.


Each night I’d limp home on sore feet and sit on my girlfriend’s bed and despair.  I remember a lone tear running down my cheek one night, followed in a few seconds by spontaneous laughter because Iron Eyes Cody – a pure-blood Italian, we found out later – currently starred in an environmental television ad as an American Indian saddened by the rape of the land, a single tear running down his cheek, which miraculously prodded Americans into picking up trash.

Iron Eyes Cody
Iron Eyes Cody

Swinging for the fence the next morning, I took a train downtown and hit all the major bars on Michigan Avenue, earning a ubiquitous thumbs down. Fingering the last $10 in my pocket, I stood at the corner of Walton and Michigan Avenue, eyeballing The Drake, where visiting Queen Elizabeth bedded down.

Too classy for my zero experience.

Looking southeast — across the street at the old Palmolive Building — I saw the Playboy Club‘s lights flashing siren lights. Shrugging off the gut instinct to stop wasting my time, I walked inside and told the smiling bunny at the door that I needed to see the human relations rep.

Who turned out to be my girlfriend’s sister’s best friend.

“You’re in luck!” she smiled. “We need a bartender pronto, and you can start Monday morning. Get here at ten for an orientation on lunch, which starts at eleven.”


The Playboy Club turned out to be a mixed blessing. Although I was able to rent my own place and start saving, the nature of the business fired up already simmering jealousies.

I’d graduated from college the previous December with an English degree and accepted the only job I could find – once again through nepotism – when Future-Mother-In-Law told me about a job opening at her school, a junior high in Chicago Ridge.

The permanent teacher was taking a year off after giving birth, and a succession of substitutes tried and failed to make a stand with her students, kids from blue collar families with moms and dads who worked long hours and didn’t have much time to spend with their offspring, so they threw money at them instead. Blue collar kids accustomed to bullying each other in the absence of parental guidance.

At six-foot-four-two-hundred-twenty-pounds I became substitute number seven immediately following Christmas break. That semester – my first in a classroom by myself – gave me the confidence to carry through the rest of life.

Years later I chatted with a man at the airport as we waited for a plane, and during the conversation we uncovered the fact we’d both taught junior high English on the South Side of Chicago.

“How long did you last?” I asked.

“One year,” he said.

“What did you do after that?”

“I quit, joined the Marines, and went to Vietnam for a vacation,” he said.


That semester I taught English to kids with names like “Toots” and “Doobie” and was required to coach 7th grade girls’ basketball; unfortunately, the 8th grade girls’ basketball coach was a conniving blonde bombshell who sensed the unease in Future-Mother-In-Law and went right to driving her nuts by sitting next to me during games, flirting whenever FMIL was in eyesight, and wearing a string bikini to the Indiana Dunes when the three of us accompanied a busload of kids at the end of the school year.

FMIL hadn’t really taught long, this being her second attempt. She’d left the profession in her early twenties to raise four children through high school while her husband, a prince, worked at US Steel.

During her free time all those years she soaked up daytime television, eventually becoming brainwashed by sexy-soap-opera-actors teaching her to trust no one – especially me – while the hot blonde simultaneously poked out of a white see-through hand-crocheted bathing suit on blazing Indiana beach while Little Richard sang Tutti Frutti from the top of a telephone pole.


When the junior high job ended and the bartender’s school landed me in the Playboy den of iniquity, my days with girlfriend dwindled.

A clean-cut Iranian floor manager named Sami started me off in a service bar out of sight from the public with liquor bottles in overhead racks, a double-sink, an ice machine, mixers, and a cash register at the end of the stainless-steel counter. The bus boys were Palestinian, the cooks Mexican. If you learned early on to treat the women right, all worked smoothly.

Bunnies would approach this portal with drink orders, and I’d pile beverages on trays before they sashayed on high heels and kidney-pinching bunny suits back to thirsty Joes elevated to Playboy Key Holders with an annual credit card fee.

The bunnies were kids like me, trying to eat under roof while putting themselves through school, putting together a stash to make a move in life, trying to survive the dollar-draining nature of the big city. There were long ones, tall ones, big ones, brown ones, black ones, round ones … crazy ones.

We were kids.
We were just kids. Laurie Proffitt, center, has enjoyed a successful photography career for decades.

And although I stayed true, my girlfriend came to visit during lunch one day — at my request — and stood in the doorway of the little service bar as I mixed drinks and piled them on bunny trays. As each female appeared, we talked business, and I often called them by name. The window I pushed drinks through revealed bunnies from their waists to their chins. Neither girlfriend nor I could see hip-tags or faces.

“How do you remember their names?” asked girlfriend as she gazed open-mouthed at the exposed set of breasts arching into the bar window.

“See that mole?” I said as “Carla” arrived with an empty tray. Having grown up on a hog farm in Western Illinois, I was not especially enamored with big breasts, though I admired their magnetic ability on the average Joe’s iron head.

Blood boiled up the chin of girlfriend’s face, onto her cheeks, then up her forehead, and with a turn of her heel I was suddenly alone in the Windy City, bereft of my only reason for being there in the first place.

The Mole
Carla’s nefarious mole.

Several months later, I’d worked my way up to the “night shift” at the main bar and enjoyed meeting out-of-town folks in the midst of convention bacchanals, though many of the women — upon reaching alcoholic euphoria —  lashed out with tongues more lascivious than any deranged Roto-Rooter man ever wagged.

One night, just after midnight on a slow shift with few people at the bar, management uncloaked in their black suits and fired every bartender on the floor.

Except me.

“You were the only one not stealing,” said Sami. “We’d been sending in people to sit at the bar and observe for two weeks now. What these dirt bags do is ring up a lower amount than they sold, then put the remainder in their pockets. Oldest trick in the book.”

One of those rounded up and kicked out of the revolving door was Howie Wong, the first bartender Hugh Hefner picked for the original Chicago Playboy Club on Walton, not far from his mansion on North State Parkway. Howie was taciturn and unfriendly, so I never knew him well.

But three months later I was walking down a side street and above a newly-painted door an electric sign flashed:  Howie’s.  Taken aback, I stepped inside and there were the six recently-fired bartenders, along with Howie at the cash register, preparing to open their new digs. Turns out they’d pooled their purloined cash – Howie dipped for decades – and opened this business. Together.

“How’s this going to work?” I asked. They just smiled and shrugged their shoulders. Six months later Howie’s was history, naturally.

Which brings me to the point of this essay.

Prisons would be more effective if we piled like-minded criminals atop one another.

As the world lurches toward nationalism and the rule of authoritarians, we need a way to deal effectively with run-away dictators.

Imagine islands – the Aleutian archipelago comes to mind with its Alaskan fresh air breeziness – islands exclusively housing like-minded criminals. Redneck Racist Island harboring Dylann Roof wannabes. Female Redneck Racist Island next door, ten thousand Rosanne Barrs separated by churning seas and hungry flesh-eating fish.

The Aleutians
The Aleutians

Black Racist Island covered with Al Sharpton wannabes. Criminal Mexican Island.  Catholic Priest Pedophile Island. White Collar Embezzler IslandWhite Collar Money Launderer Island. Rapist Island. Man-Trapping-Liar-About-Rape Island.

Ad infinitum.

The unending torture of individuals imprisoned under these conditions would test the “cruel and unusual” clause under the Eighth Amendment, but this treatment would be justified due to its effectiveness and ultimate benefit to society.

Can you imagine a self-aggrandizing, constantly lying, narcissistic blowhard in a green parka – absent makeup – wielding a hand-ax, a book of matches, and some fishing gear, and marooned for life on a frozen slag heap in the middle of an ocean with hundreds of other convicted narcissistic blowhards and a few Kodiak bears on Russian Money Laundering Island?  A pleasing and peaceful thought, indeed.

Perhaps the perfect prison doles out the perfect punishment.

For those of you who bless your children by reading to them, check out “The Girl Who Trod on the Loaf” by Hans Christian Andersen. It’s the story of a girl who loves pulling the wings off of insects, but her bullying comes to a bad end:

An evil spirit soon took possession of Inge, and carried her to a still worse place, in which she saw crowds of unhappy people, waiting in a state of agony for the gates of mercy to be opened to them, and in every heart was a miserable and eternal feeling of unrest. It would take too much time to describe the various tortures these people suffered, but Inge's punishment consisted in standing there as a statue, with her foot fastened to the loaf. She could move her eyes about, and see all the misery around her, but she could not turn her head; and when she saw the people looking at her she thought they were admiring her pretty face and fine clothes, for she was still vain and proud. But she had forgotten how soiled her clothes had become while in the Marsh Woman's brewery, and that they were covered with mud; a snake had also fastened itself in her hair, and hung down her back, while from each fold in her dress a great toad peeped out and croaked like an asthmatic poodle. Worse than all was the terrible hunger that tormented her, and she could not stoop to break off a piece of the loaf on which she stood. No; her back was too stiff, and her whole body like a pillar of stone. And then came creeping over her face and eyes flies without wings; she winked and blinked, but they could not fly away, for their wings had been pulled off; this, added to the hunger she felt, was horrible torture.

"If this lasts much longer," she said, "I shall not be able to bear it." But it did last, and she had to bear it, without being able to help herself.

The perfect ending for a bully’s sad life.

Similar to an immortal history book full of verifiable facts, I reckon.