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Chicago Stories

Stephen P. Conrad


“Don’t send nobody, nobody sent”

To paraphrase one of Chicago’s great writers; Loving Chicago is like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real. — Nelson Algren, Chicago: City on the Make. I mean that pretty much sums it up right?

Chicagoans can be clannish, it’s a city of tribes. The Irish as they have for most of the Twentieth Century ran this game. The Outfit guys had the rackets, gambling and juice loans, the Greeks had the diners, the Jews the delis and Jewelers Row and the Irish had the politics. The quasi-legal rackets. You get my drift; everybody got a piece of the pie. Maybe not always an evenly cut piece, you had to know how to fight for your fair share.

I’ll never forget the first time I ever stepped into the Chicago 11th Ward headquarters aka the ‘Promised Land’ to machine faithful. I was sent with an envelope by my boss who was a trusted servant of the man on the ‘fifth floor’, where the mayor sat. Therefore, I was trusted.

As I pulled up in front of the less than average looking stand-alone brown brick building, just as they had instructed, there was a parking spot waiting for me. Not an easy get on any street in Chicago.

On door duty was a large man in a cheap suit inhaling a sandwich whole. Probably a Streets and San guy was my guess. He gave me that ‘look’ as I stepped through the doorway into a time warp.

It was musty and dimly lit. Probably on purpose. You don’t want people to get too comfortable and loiter around all day. Sparsely furnished, an entire wall was dedicated to the fully stocked bar. Folding tables were set up around the room covered in maps like fine holiday tablecloths. Ward maps. After all that was what this was all about, winning city political Wards.

I had been in a few other political war rooms before but nothing quite like this one.

Everyone who was anyone had passed through this door, from movie stars to gangsters, and presidents, probably even Jack Kennedy himself. JFK’s picture hung on the wall, aside of Pope John Paul II and ‘hizzoner’, the Honorable Richard J Daley himself, ‘da mare’. (For those unfamiliar with the colloquialisms of the Chicago streets, ‘hizzoner’ or ‘da mare’ is the mayor) The holy trinity. Da Mares son Richard M. ran the show now. Richie da first and Richie da second, like royalty.

The stink of thick cigarette smoke mixed with stale air and an abundance of caution bordering on paranoia polluted the room. The brims of ashtrays overflowed with chewed cigar and cigarette butts, not a hint of lipstick on any. This was a man’s room, misogyny central. If intolerance existed in Chicago, it started here along with a few other -isms. At best, it was controlled chaos.

In the 11th Ward fortunes are made and fates are decided, some win and some lose and it’s never by accident. Within its four walls presidents have been made and governors have fallen from grace. Machine politics live and breathe in the 11th Ward HQ. Hell, they were invented here. The ‘machine’ to Chicagoans who are in the know is what outsiders refer to as the Regular Democratic Party.

In Chicago, you’re either inside the room or on the outside looking in. It can get cold outside. It’s not easy to score a ticket to the party, I got lucky. My Chinaman spoke up for me. I was back doored into the machine.

As I crossed the room every eye was on me. I walked like I belonged in this alpha-dog world, even if I had to fake it. I had a task to complete and that was to make certain the nondescript manilla envelope I carried made it into the hands of the man who mattered.

I had no idea of its contents, nor did I make an inquiry when sent off on this mission. I was after all, the unknown, the new kid. Could I be trusted? That was the question in everyone’s eyes.

One of the ten city hall commandments, “don’t send nobody, nobody sent” crossed my mind. It meant don’t send nobody we don’t know to us, through a friend or otherwise. My Chinaman, the Honorable Marty Hogan had taught me that. This was the first time I understood what it really meant, and I never forgot it.

In that moment all I could think to myself was — the stories these walls could tell. Then I realized they were probably bugged anyway. It was in this room, amongst these men, relationships were born, a handshake is the blood covenant, futures are assured, uneasy alliances determined history.

I learned a lot in my first few minutes in that room, I was easier to teach back then. I wasn’t already totally jaded just a bit wearied.

I learned the guys in the tracksuits and pinky rings, the big shots, weren’t and the guys who didn’t play the part, were. It was the red faced, rugged looking guy with catcher mitt sized fists standing in the corner of the room dressed down in flannel shirt, dungarees and work boots. Now he was the guy, the real Chinaman, the head Rabbi, the king maker. But isn’t that the way it always is? It is in Chicago at least.

Chicago is if nothing else a city without a mask, a city of wide-open secrets, a city of stories. Those stories fill every neighborhood tavern, swirl around every dimly lit street corner and are used like currency in every Loop high rise office.

There are stories whispered in every downtown diner booth with spitting distance of city hall and bragged on in every el train car. Like mortar between bricks, they are what binds us together and keep us from falling apart.

Those people that are put into elected office are expected to bring home the bacon. Everyone loves to hate the politicians who bring it home, but there’s an unspoken understanding, ‘don’t send nobody, nobody sent’. Joe Citizen doesn’t care what goes on in Springfield or D.C., or how you get it, just bring it home. Just do it!

It’s a city of hopes and dreams realized. It’s a city that takes care of its own. It’s a city with a lot of stories.

People love good a story, they are the very essence of who we are, where we come from and where we hope to go. In Chicago you can tell who someone is by what tavern they drink in, the place of worship, and at what park they play sixteen-inch softball, a Chicago thing. Some say, even Capone mobster “Machine Gun” Jack McGurn sponsored a 16-inch team.

A good story is passed on from a barstool in every tavern to a pew in every church, and from every Ward to every Precinct to every neighborhood. Passed on from generation to generation until they become part fact and part fable.

Our own story shares with others just a tiny bit about who we are and what we are made of. Happy or sad, exciting or tragic, everybody has a story, and every story is by the natural order of things at some point related. Chicago is a city built on relationships and a handshake and in every handshake is a story.

Why Chicago? Why not? It’s my home. Sure, I’ve lived in other places for varying amounts of time, yet I always return to her. She’s like your first kiss and the best escort you’ve ever had all at the same time.

For better or worse I can’t forget them or what they taught me. As with most relationships in my life Chicago and I share a sort of twisted but comfortable union. Maybe it’s because in her embrace I can survive, even thrive and feel safe if only for an evening.

At the end of the day, I am a through and through Chicagoan. Our relationship? It’s complicated really, it’s a love hate thing. I love her for everything she is and all that she can be, but I hate her for what she at times becomes.

I love that she can be those things that I can also hate because it’s those things that make her what she is and what she has taught me to be, a survivor. I love her characters that couldn’t exist anywhere else. I love the stories her characters want to tell.

We all have a story to tell. Whether or not we admit it we all want others to know our story. It’s important to us that we be remembered.

It’s the stories of those characters that make up what Chicago is.

Some of us share our story freely, others need to be coaxed, some need to have them pried out of them. Some are pleasant, some are not, some are filled with fond memories, others sadness, and despair, many overwhelming, most are somewhere right in the middle. None of them are boring.

The sum-total of our life experiences is what we what we are made up of. Our individual stories determine our character and there are a lot of characters in Chicago.

I’m here to help them tell their stories.

So, stay tuned.



Stephen P. Conrad

A nomad, a gypsy at heart, writer, actor, artist, anti-sycophant, socially maladjusted and comfortably near complete insanity.