Scenes from Chicago’s Ewing Annex Hotel, the Last of Its Kind

During my visits, I met several men who told me that after completing programs at

During my visits, I met several men who told me that after completing programs at Thresholds, an Illinois nonprofit that supports people with mental illness and substance-use disorders, they were “sent” by Thresholds workers to the hotel. From that point on, they live at the hotel while social workers managing their supplemental security income money come in once a month to pay their rent. Thresholds told me that while they don’t have a “formal relationship” with the Ewing, they do manage rent payments on behalf of some men who live there, who are also enrolled in Threshold programs, via a process known as representative pay

“During this pandemic, a lot of these guys work either day labor places or in factory settings where they wasn’t able to go to work,” Mike tells me. Although the CDC moratorium on evictions doesn’t include hotels or motels, no one was evicted from the Ewing. Indeed, resident after resident tell me stories about how at some point during their tenure, they were unable to pay rent for weeks that turned into months, but they were never threatened with eviction. Instead, Mike works out deals with men who need them. If a resident usually pays by the week, for example, when they start making money again, they would resume paying by the week, “plus a couple few dollars toward what they owe.”

The entrance to the Ewing Annex Hotel in Chicago on March 30, 2021

Over the years, in an attempt to help his aging, ill residents thrive, Mike has connected regularly with local organizations like The Night Ministry, which provides health care to people who are homeless or in poverty. In 2020, they stopped by twice to administer Covid-19 tests, but he wants more care, and he wants it from the city. Mike’s angry. “We should be able to get somebody to come, a company to come through that specialize in sanitizing hospitals for the virus,” he says. Even though they’re eligible, it would be very difficult for many residents to make an appointment at the United Center, where the city has set up mass vaccinations for eligible residents, let alone to get there and back twice. He wants the health department to come by and vaccinate residents but tells me he’s given up on calling them. For now, The Night Ministry has been able to provide first doses to a handful of men at the hotel.

In 2013, two aldermen tried to shut down every cubicle-style hotel left in the city. One of them, Alderman Brendan Reilly, whose ward borders the Ewing, said, “Average Chicagoans wouldn’t want to house their dogs in this type of facility.” Housing activists, along with the residents of these hotels themselves, pushed back against that language, which they found insulting, and against the closure of their homes without any input from the residents themselves. Mike shows me the handmade T-shirts he and others wore to ensuing City Council meetings and protests. “Please Don’t Make Us Homeless,” they read. Ultimately, the proposed ordinance did not pass, but eight years later, the Ewing Annex Hotel is the last of its kind. 

Several men told me that although the Ewing is noisy, at times dirty, and the bedbugs drive them nuts, here they’re able to come and go as they please, with their autonomy and dignity intact. There are no benchmarks to meet, no curfews, no religious services they’re required to attend in order to keep their beds. This is their home; they choose it. In their home, these men deserve, like everyone else, to live safely and well. 


Death comes to the hotel unevenly, but it does come. Some years, two men die. Last year, it was eight. They pass from old age or overdose, heart attack or stroke. This is why he asks for emergency contacts during check-in, Mike explains to potential residents. He’s seen too many men buried unclaimed, unmourned, but not alone—in Cook County, unclaimed remains are cremated and buried up to 20 urns per casket—to not try and get a name and number for each resident’s records, just in case. 

Several years ago, an 86-year-old named Sid Weinstein called Mike from the hospital and asked him to bring something. He’d lived at the hotel even longer than Mike, and while Mike used to sometimes give him rides back and forth to doctor’s appointments, they weren’t exactly friends. Sid didn’t really have those. Fairly regularly, Mike would be in the lobby, checking someone in and minding his business when the sound of stomping and shouting would drift in through the old floorboards above his head. 

“Two old guys, slipping and sliding on the floor,” Mike tells me. He shakes his head, but his eyes are smiling. “One throw a punch and miss, the other throw a punch, he misses.” Each time, Mike would give them a minute of dignity before breaking it up. “Okay. You swung enough, guys?” Panting and glowering, Sid and his neighbor would slink back to their rooms.

A Jewish, white, hot-tempered veteran and a Black artist whose whole life had been a lesson in the necessity of de-escalation for survival, they had little in common but the address they shared. But when Sid called, Mike answered. Mike no longer remembers what it was that Sid asked him to bring to the hospital that day. He only remembers what Sid told him once he was there.

‘Before you leave the hospital today, I need to talk to you about something. I’m gonna trust you to take care of my business when I pass. Here’s my bank card. There’s enough money to bury me decently,’” Mike recalls. “Do that for me,’ Sid said. ‘Whatever is left in the account, I want you to have.’”

Mike knew Jewish burials had to be done a certain way, but he didn’t know what that way was, and Sid died in the hospital before Mike could ask. In between his duties as the hotel manager, he tried to learn. He also wanted Sid to get a military burial, full honors, but he says the V.A. never returned his calls. Finally, the funeral home rang. They couldn’t continue to hold Sid for much longer. 

So Mike, the way he’s done countless times before as manager of the Ewing Annex Hotel, made the best decision he could with what he had. He took out a plot for Sid in the military section of the cemetery, thinking that at least then, he’d be among comrades. He picked a nondenominational service. Mike felt bad that time had run out before he could sort out what Jewish rites to follow. He felt worse on the day of Sid’s memorial when, among all the chairs the funeral home staff had set up for mourners to come and pay their respects to this old, fighting man, he mostly sat there alone. “Nobody should have to go like that,” he says.

As Mike sat at the service with his artist’s eye for detail, he paid attention. He noticed the light coming in the windows and how it hit the floor. He watched as a woman with long, gray hair and a fur coat strode in, whispered something to Sid’s casket, and took a seat, where she remained until the memorial’s end. And he saw, once outside after the memorial’s end, the Star of David engraved above the door. It was then that Mike realized: In a previous life, until the mid-twentieth century, it had been a Jewish funeral home. 


Mike is really good at his job. He notices detail and cares about people. “Well,” he says quietly after I tell him this, “somebody cared about me at one time.” After the summer of 1968, Mike qualified on scholarship to attend weekend classes at The School of the Art Institute of Chicago for three more years. During those classes, he made sculptures, watercolors, and sketches. 

The care Mike takes of the Ewing and the men who call it home is obvious but so is the labor required to, in so many ways, pull it off alone. It’s why he’s quitting, I think, or part of it. He’s excited to leave. He’s excited to pursue his art; to mount an exhibition; to live out a wonderfully boyish dream of living in a repurposed firehouse, sliding down a pole from his bedroom to his art studio every morning; to finally go home to Memphis, the place he’s never quite gotten over. But while avoiding sanctifying him, I don’t know what the hotel is going to be like without him.  

An empty room at the hotel

In my eyes, the city, and perhaps other institutions with power, have come to rely on the hotel to catch men they otherwise would let fall through. But it’s a reliance based on evasion; as long as they don’t look too closely, they don’t have to do anything about it. When they do look closely, some see a hotel from a nearly bygone area that’s “not fit for dogs” taking up space where high price condos, and the different clientele they bring, might be. But these men aren’t bygone. They’re still here, in this hotel that some of them hate and some of them love and all of them call their home.

Mike is right, of course, to remind me that it takes no special goodness to pay attention to someone–only effort, repeated, ordinary, every day. It’s also right to note that the fate of hundreds shouldn’t rest on the effort of one, especially not when powerful institutions seem to quietly rely on that one to do their work. Perhaps this effort to pay attention only seems natural to Mike because he’s done it all his life–so much so that it’s become a reflex of his, allowing him to see deeper, look further, walk by empty schools and imagine finally housed families, to look at closed factories and see something life-giving and real underneath the surface of what’s been present all along. The drawing he made and submitted that summer, just shy of 13 years old, when the rest of his life was wide open and waiting to begin? A beautifully rendered, anatomically correct drawing of a human heart.

This story was published in collaboration with the Chicago Reader.