Sloppiness is a trait that rubs Doug Jennings the wrong way, so he stopped me one morning near the corner of 80th and Ashland.
Jennings headed into a dollar store to bum a cigarette, not having any of the cheap roll-your-own kind he prefers. Rebuffed by a clerk, he continued his quest. Briefly he took the keys off his shoulder, swung them in the air, then put them back where they’d been. At the gas station at 79th a friend on crutches gave him a smoke. Jennings entered the Rothschild Liquor Mart and purchased a fifth of Richards Wild Irish Rose, his beverage of choice since he was a teenager. He just turned 55.
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Jennings has been amassing keys since 1983. “I was going with this lady named Peggy Brown, and her father, who worked for a moving company, had a bunch of skeleton keys,” he says. “He asked if I wanted them, and I said yeah. I hooked them together and started carrying them around.”
Jennings, a slim man with a mustache and goatee, is a fixture on the south side, walking about slowly. “What’s the point of hurrying?” he says. He prefers the alleys to the streets. “You meet good people in the alleys,” he says. “They’ll be sitting down, drinking and talking. And you don’t have to step on anybody’s toes like you do on streets.” On the blocks near his sister’s apartment people know Jennings as Uncle Doug, but farther afield he’s called the Key Man or simply Keys.
When he emerged, Jennings married a young woman named Lucinda he’d met at the hospital. They had four children. They’re still married. “We don’t believe in divorce,” he says. “Till death do us part, and all that means. She’s my best friend. But I don’t know where she is.” He’d later have one more child with Peggy Brown.
Eno Ekong, a real estate investor and rehabber who has employed Jennings in the past, is bothered not by the keys but by Jennings’s behavior. Ekong says Jennings drinks too much, fails to obey instructions, and attracts undesirables. Jennings doesn’t much care, especially about the drinking. When he tried sobriety in 1989, he says, he ended up taking his clothes off in a forest preserve and the police had to be summoned. “If I gave up drinking now I’d probably die,” he says. “I’m not giving up no kind of habit that I got.”
