One of the things that struck Lloyd DeGrane when he began photographing Chicago’s chronically homeless four and a half years ago was their own conception of themselves. “When I’d invite them into a coffee shop or a McDonald’s to buy them a hot drink, they’d ask, ‘Are you sure it’s OK to bring me in here?’ ” DeGrane’s subjects, he says, “see a distinct separation between themselves and other people. They’re very aware of it.”

And yet the homeless are all but invisible to many Chicagoans. Lifting that veil is in part what motivates DeGrane. For this project, which began as a Medill School of Journalism fellowship, DeGrane has immersed himself in this shadow world, getting to know his subjects intimately and learning their argot: Some “fly a sign,” scrawling a message on cardboard to panhandle; others are “scripters,” using a memorized spiel to hustle for spare change; still others are “boosters,” engaging in petty theft. Some are addicted to opioids. Many are estranged from or maintain only a tenuous connection to their families. A few have children of their own.

DeGrane carries a backpack containing his camera and an extra lens — never a tripod, which can attract the attention of thieves — as well as cigarettes (“Newport 100s are popular,” he says) and Hershey’s Kisses (“People addicted to opioids seem to crave sweets”) to offer as icebreakers, clean syringes, and the overdose-reversing drug naloxone, commonly known as Narcan, which he has had a couple of occasions to use. He spends two to four days each week on the streets, walking up to 12 miles a day, often concentrating on an area stretching north from Chinatown into the Loop. Sometimes, DeGrane accompanies volunteers from the Night Ministry, a nonprofit, and members of the Chicago Street Medicine team, who value the photographer’s ability to gain the trust of the men and women these organizations are trying to help.

“The people I photograph are my friends,” says DeGrane. “I’ve known many of them for years now. I know their struggles, and I see the toll homelessness takes on their mental and physical health.” Of the 200 or so subjects he has come to know well, at least 25 have died. A few, though, have gotten off the streets. “I’ll get a Facebook message saying, ‘You’re not gonna see me downtown anymore, I just got a job. I’m home.’ ”

Reggie (above)
Pedway at Millennium Station
“I think of Reggie as the gatekeeper to Lower Wacker,” says DeGrane. “When I met him, he was planted on a walkway leading to the trains, with a cup in front of him, his head down, with a sign that just said ‘Homeless, Need Help.’ I offered him a coffee and a Newport, and we started talking. He knew a lot of people down there, and he’d introduce me, saying, ‘This guy’s OK. You can talk to him.’ I was able to fix him up with the Street Medicine team and get him into a program called Better Health Through Housing. Now he’s got a small apartment.”