Sloppiness is a trait that rubs Doug Jennings the wrong way, so he stopped me one morning near the corner of 80th and Ashland.

“Your jacket collar is tucked into your shirt,” he said. I fixed myself up, thanked the stranger for his thoughtfulness, and watched him amble off. I couldn’t help noticing the thick chain holding dozens of keys slung over his right shoulder, reflecting swirling bits of sunlight onto his green Michigan State Spartans jacket.

“What’s with the keys?” I asked him.

“I collect ’em,” he said. “They’re the keys to my broken heart.”

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.

“Usually I have a drink when I start walking someplace,” Jennings says. “With the keys I forget about drinking until I get where I’m going. They make me feel comfortable.”

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.”

The keys are acquired all over. “Somebody’ll go into a grocery store and leave their keys on the counter,” Jennings says. “They won’t come back, and the owner’ll give me the keys. Other keys I find on the street. I don’t steal any of them or nothing.” His chain contains bike, gas-tank, locket, luggage, and jewel-box keys, plus plenty of keys to automobiles, principally from American manufacturers. “I don’t even know how to drive,” he says.

He totes the keys from March or April until November, when the chain becomes too cold to carry. Then he stows that year’s supply in the basement of the bungalow he shares with his sister and her family on South Justine. He never reuses a chain. He can identify past sets from their adornments: 1997’s chain has a bullet and some handcuff keys that he found on the pavement; 1998’s has an old-fashioned sink fixture; 2003’s has a brass belt buckle. None of the chains has any plastic. “I don’t like plastic,” Jennings says. “Everything I have has to shine.”

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.

“I’m stopped every hour or so,” he says. “Teenagers try to pick a fight with me. ‘I bet you can’t beat my ass with those keys,’ they say, but I put my head down and keep on walking. My keys aren’t a weapon. I’d never use them for that. Never had to.

“Lots of times it is little kids on the bus who speak up. ‘Oh, mom, look,’ the kids will say, and then I let them hold the keys. But I been kicked off a bus because of the keys, too, when this woman driver got scared and called the cops. Usually the police are no problem. They pull me over, check me out, and I’m off again.”

Jennings tells some curious people that when he went to jail he got tired of hailing the turnkey. “I’m looking for a chastity-belt key,” he’ll say to others. “Now if I find a woman, I’ll have to find that key.” If that one falls flat, there’s always the crack about the keys being to his broken heart. “That’s how I meet women,” Jennings says. “‘I wouldn’t break your heart,’ the girls say, and we get to talking.” The relationships that result are fleeting, he says, just for sex. “I don’t want no more girlfriends. They’re a headache.”

The son of two railroad workers, Jennings grew up on the west side. He was 12 when he first ran afoul of the law. “They said I pulled up a lady’s dress in Douglas Park,” he says. “They took me to the Audy Home and then, because they didn’t know what to do with me, to Chicago State [now Chicago Read] mental hospital. I was in the nuthouse for four years.”

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.

Jennings held a number of jobs–picking up paper for the Park District, doing janitorial work at John Marshall Law School, toiling at an envelope company–while maintaining a sideline of snatching purses. “I was good at that,” he says. “I got away with most of the purses, but then I got caught.” It wasn’t until 1973, after his fourth turn behind bars, that he gave it up.

He worked for a cousin who ran a taco stand, then took up house painting, the steady nature of which the cousin thought would discourage Jennings from drinking. He did maintenance on some northwest-side buildings and manned a paper stand owned by a son-in-law. He developed a trade helping women with their gardens and chores. Lately he’s been house-sitting for rehabbers who want to make sure they aren’t ripped off at night. His current gig, which pays $150 a month, has him sleeping at a two-flat in Englewood. “I got a little mattress there, some blankets, a TV, and a radio,” he says. “When they turn the gas on, I’ll be able to cook up something to eat.”

In 1996 Jennings’s son Douglas Jr. died of AIDS; later that year so did his best friend, Willie Christler, who went by the nickname Napoleon. “Doug and Napoleon were inseparable, like Siamese twins,” says their mutual friend Art Conley. “When you’d see one, you’d see the other. They lived together for a time. Doug had been collecting keys all along, but since Napoleon passed, they have become an obsession. It takes his mind off the loss, I think.”

His employers all notice the keys, but don’t seem to mind. “If Doug wants to burden his shoulder with those keys, that’s up to him,” says Dorothea Campbell, an elderly West Pullman resident for whom Jennings paints, moves furniture, and does yard work. “Doug is not nasty or messy, but very nice. When he comes to me he sets his keys down by the house and gets to work.”

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.”

Art accompanying story in printed newspaper (not available in this archive): photos/Kathy Richland.