The following story is a work of fiction. Names and details have been changed to protect the innocent, the guilty, and my pension. Any resemblance to real people or events is purely coincidental. This is not true.
The garbage got picked up. The snow got plowed. The potholes got filled.
The nephew got the contract. The cop got free coffee. The alderman got his envelope.
Nobody cried about it. Everybody understood the deal.
Your guy took care of you. You took care of your guy. The city kept moving.
That was Chicago. Grease. Favors. Handshakes.
And everyone was cool with the way it worked... because it worked.
Mayor Richard J. Daley
We’re talkin late ’90s. The very end of The Good Old Days.
Grossberger was a young rookie then. He already had a guy who called when “items fell off the back of a truck.”
That’s how his guy said it. Not stolen property - Items.
Chicago had code words for questionable things- things you didn’t ask about.
A guy didn’t have stolen property- he had items.
Nobody was corrupt- they were connected.
You didn’t get paid off- you got taken care of.
That’s how the city talked when everybody knew what was going on- and nobody needed it said out loud.
One night, Grossberger was working alone when his guy called with some extra cases of wine - he found.
Fast forward fifteen minutes to a dimly lit garage in Bridgeport, cases stacked to the ceiling, Grossberger points. “Give Grossberger those and those.”
No plan. No buyer. No idea what to do with them.
Grossberger don’t know shit ‘bout wine. Grossberger don’t give shit ‘bout wine. Grossberger don’t pass up good deal.
They filled the trunk of his squad car and he drove downtown.
Summer night. Restaurants packed. People on the sidewalks. Girls in dresses. Titty’s are out.
Valets running exotic cars. Music coming out of bars. The whole city lit up like Vegas.
Chicago at its best.
And there’s Grossberger. Crushing the hood of a marked police car. With a trunk full of wine.
A couple girls he knows walk by.
“Girls like wine?” “Yeah, we like wine.” “Girls buy wine? Cheap.” “Sure.”
Pops the trunk.
Right there on the Street. Not in an alley. Not behind a warehouse. Not under a viaduct. Right there in the bright lights of the Gold Coast, while people are eating dinner ten feet away.
Grossberger starts selling wine out of the trunk of a police car.
The girls pick out a couple bottles. They do the math for him.
Grossberger take money. Grossberger make change. Close trunk. Goodbye. Business conducted.
To himself - “Grossberger do this all night. Grossberger get rich.”
Then he looks over. Captain McCluskey is sitting in his car - Watching.
Now you have to understand something. Captains don’t just show up out on the street. Captains have important Captain responsibilities. Meetings. Phones. Signing paperwork and arrest reports.
The Captain is ultimately the Boss, responsible for every single thing that happens in his district that night.
Lieutenants, sergeants and patrolmen work the street. The Captain holds down the fort.
Seeing the Captain out on the street, was like seeing the Pope drunk in the basement at Spybar. Unusual and Unexpected. But he is from Dolton so it’s not completely Unbelievable.
McCluskey curls his finger. Come here.
Grossberger waddles over - oblivious. “Hello, Grossberger Captain.”
McCluskey looks at him. Real calm. Real serious.
“Did I just watch you open the trunk of your squad car... and sell bottles of wine?”
Grossberger now starts to realize what he did. In uniform. On duty. Standing next to a marked police car. With a trunk full of “extra wine.”
To himself - ”Grossberger make change like liquor-store clerk.” ”Grossberger Captain see everything.” ”Grossberger Fucked.”
There’s a moment in every idiot’s life when the full weight of his idiocy hits him right in the sack. This was that moment.
The Captain repeats - “Did I watch you sell booze out of your trunk?”
Grossberger responds - “Yeah... Ugh... Grossberger guess Captain did watch.”
Grossberger waits - Desk duty? A suspension? Grossberger Fired?
Questions - Comments - something you’d like to know or hear about? Leave a comment or send me a message.
I’ll be posting weekly stories from the streets of Chicago as a former Cop - as Head of Security on The Jerry Springer Show - acting on TV and in Movies, and more insane life experiences. Several I shouldn’t have survived.
Pete - great story but kind of sad too. I was lucky to be in Chicago in the 90’s when Chicago ‘worked’. Then I watched it crumble. I came from NYC and watched that crumble too. Your story made me think back to the old days when everything ‘worked’. It brought back great memories - but fading ones. A good writer makes you think long after reading what they wrote. You are a good writer Pete.
Somehow it worked, until it didn’t. Thanks Pete. Well said. I enjoyed reading your story and look forward to more. Brings back memories.
Pete - great story but kind of sad too. I was lucky to be in Chicago in the 90’s when Chicago ‘worked’. Then I watched it crumble. I came from NYC and watched that crumble too. Your story made me think back to the old days when everything ‘worked’. It brought back great memories - but fading ones. A good writer makes you think long after reading what they wrote. You are a good writer Pete.