Kyle Tequila

This is a 1970s-era Board of Tourism advertisement for the city of Chicago. Chicago is fun! It's overflowing with sunlit cityscapes and joyful, smiling faces of young people, families, and tourists, all locked in a state of perpetual 8-millimeter textured happiness and wonder of this city of broad shoulders, this great city by the lake.

This is a 1970s-era Board of Tourism advertisement for the city of Chicago. Chicago is fun! It's overflowing with sunlit cityscapes and joyful, smiling faces of young people, families, and tourists, all locked in a state of perpetual 8-millimeter textured happiness and wonder of this city of broad shoulders, this great city by the lake.

It really does look like a wonderful place to live. A place with endless possibilities, where anybody, no matter who you are or where you came from, can get a fair shot at the brass ring.

It really does look like a wonderful place to live. A place with endless possibilities, where anybody, no matter who you are or where you came from, can get a fair shot at the brass ring.

But only a few miles from the bright lights of Michigan Avenue is a different stretch of road, a dark corner of the Windy City you won't see in any Board of Tourism commercial.

But only a few miles from the bright lights of Michigan Avenue is a different stretch of road, a dark corner of the Windy City you won't see in any Board of Tourism commercial.

It's a place where the cops are just as crooked as the criminals, where drugs and prostitution run rampant, and where a young mafia hitman they call The Kid is parked outside of a dark, dilapidated apartment building, waiting for just the right moment to make his next move.

It's a place where the cops are just as crooked as the criminals, where drugs and prostitution run rampant, and where a young mafia hitman they call The Kid is parked outside of a dark, dilapidated apartment building, waiting for just the right moment to make his next move.

Holy shit. I'm your host, Kyle Tequila. Welcome to Crook County.

Holy shit. I'm your host, Kyle Tequila. Welcome to Crook County.

Episode 1. Give me your fucking money.

Episode 1. Give me your fucking money.

Uh-huh. All right. I'm interviewing Kenny, the kid, for the first time. Okay. He's a big man, in his mid-60s, with a full head of jet black hair, combed and styled with only a few strands of gray, wearing a clean white t-shirt and reading glasses with thick black frames. He's handsome, in a run-down sort of way. He kind of reminds me of a down-on-his-luck Clark Kent. You know, Superman, but fat.

Uh-huh. All right. I'm interviewing Kenny, the kid, for the first time. Okay. He's a big man, in his mid-60s, with a full head of jet black hair, combed and styled with only a few strands of gray, wearing a clean white t-shirt and reading glasses with thick black frames. He's handsome, in a run-down sort of way. He kind of reminds me of a down-on-his-luck Clark Kent. You know, Superman, but fat.

Let your brain go. He's not used to having a microphone in his face and seems to be having a little trouble getting comfortable with me.

Let your brain go. He's not used to having a microphone in his face and seems to be having a little trouble getting comfortable with me.

It goes on like this for a while, but eventually he starts talking.

It goes on like this for a while, but eventually he starts talking.

Kenny spent over 20 years working deep inside the legendary Chicago Mafia, also known as the South Side Gang, or simply The Outfit, which rose to power in the 1920s during Prohibition under Johnny Torrio and Al Capone.

Kenny spent over 20 years working deep inside the legendary Chicago Mafia, also known as the South Side Gang, or simply The Outfit, which rose to power in the 1920s during Prohibition under Johnny Torrio and Al Capone.