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What's So Funny? Profiles of the local and eccentric: Chicago

Chicago, Squire Lounge, Denver, East Colfax

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“Yo, yo, Chicago in the house!”

Chest puffed like a peacock, Chicago is his own hype man, a carnival barker trumpeting his own arrival. You can’t miss Chicago. He wears a construction worker’s hardhat; his long, braided beard hangs halfway down his ribcage. And that stretch of Colfax between York and Park Avenue West? Chicago owns that stretch. He’s the arbitrator of homeless disputes there, and, when necessary, the instigator. People listen to Chicago. He keeps two knives on him at all times. They listen. 

“Yo, what’s the best thing about dating a homeless chick?” he asks.

It’s Tuesday, open-mic comedy night at the Squire Lounge, and Chicago’s telling jokes out front for money or smokes, for camaraderie. Same hustle, different day; begging for change, just in joke form. He’s not allowed inside the Squire, though. Chicago’s explanation why differs vastly from that of the bartenders there. Chicago’s knives were involved but beyond that, two completely different tales.

“I don’t know, Chicago,” someone says. “What’s the best part of dating a homeless chick?”

“You can drop her off anywhere! Let me finish your cigarette.”

“Yo,” he continues, “why did the blond girl go to church?”

“I don’t know, Chicago. Why?”

“Because she heard there was a dude in there hung like this.”

Chicago stretches his arms out, Christ on the cross. He says “dude” like “dood” and “this” like “dis.”

“Yo, you want to buy this portable CD player?”

It wasn’t always like this. Born on the South Side of his namesake city, Chicago used to be a working man, he says. He got married and his wife was transferred to Buffalo, N.Y., so he went with her, picking up work at Excelsior Orthopedics, then Buffalo Powder Coating. They hated the cold; he told her to transfer out West, somewhere warm, like Arizona. She landed here.

That’s when Chicago says he started working for “Ms. Gates” (of Gates Rubber Company fame) as her assistant. He helped her with whatever she needed. Driving Ms. Gates in her convertible to the grocery store, she would let him get anything he wanted.

“I used to get the 5-pound crab legs,” he says, measuring the size between his gloved hands. “Real high class.”

But the high life came to an abrupt halt for Chicago. His wife left him for “some dude she met on the Internet.” She was pregnant with Chicago’s kid, but she split with her new boyfriend anyway. She took everything including the baby.

So Chicago gave up.

But wasn't he a working man? “I gave up,” he says, conclusively. “I started living on the streets and that was that. I wanted to kill myself. I wanted to jump out of a window. I threw myself in front of a bus four times. You know how good those brakes are on RTD?”

That was eight years ago, and he says he’s been homeless ever since then. He’s been arrested more times than he can remember. For loitering, public intoxication, trespassing.

“Trespassing?” he asks rhetorically. “Walking down Colfax? What about the guy driving drunk with no headlights? Arrest him! It’s a farce! A farce!”

Chicago says he was asleep a few weeks ago in Cheesman Park when a cop woke him up with a kick to the ribs from his steel-toed boot. Move it along, the cop told him. “They’re always fucking with me.”

It’s a farce.

A place is all he needs. Nothing fancy—a van even—but if he just had somewhere to lay his head at night, Chicago thinks he could bounce back. But he’s not betting on it. He’s going to die this year. That’s what he thinks, anyway. His sciatica’s so bad he can hardly lie down. Last year he had frostbite and the doctors at Denver Health wanted to cut off his foot. He wouldn’t let them; now he walks with a cane half the time. At 44.

Still he patrols his stretch of Colfax the best he can, occasionally with a busker’s flare. He can pop open the Denver Post kiosks with a deft push and a pull, a nifty trick he’ll show you if you ask nicely enough. He has elaborate pounds hello for everyone he meets; a snap, a dap, a point of the finger. Some of the businesses like him enough to let him use their bathrooms; others give him the cop treatment. Move it along, Chicago. So he does. He still has a lot of fight in him, but not for meaningless battles. Keeping warm is hard enough. It’s too cold to sleep at night so he limps around until the sun rises. Occasionally he crashes at a buddy’s apartment, but for the most part, Chicago stays on the streets, this stretch of Colfax now his home. It’s a far cry from indoors, but it’s where Chicago is definitely in the house.

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