The Run Down

We're headed to Chatham on Chicago's South Side. For this guide, we met up with Jahmal Cole, founder of My Block, My Hood, My City, a Chicago non-profit organization that works with students from under resourced communities, and takes them on city explorations throughout Chicago. He takes us around his neighborhood to grab giant donuts, have a plate of chicken and waffles, and tell his story.

1. Lunch @ Captain's Hard Times Dining

2. Explore @ Historic Brick Bungalows

3. Giant Donut @ Dat Donut

1. Captain’s Hard Times Dining
(AKA Josephine’s Cooking)

We begin this guide at Captain’s Hard Times Dining (now known as Josephine’s Cooking), a soul food diner near the corner of 79th and Martin Luther King Dr. We’re here to have breakfast with Jahmal, and we’re doing breakfast the best way we know how — with a plate of chicken and waffles, coffee, and good conversation.

This is Jahmal. As we dig into breakfast, he tells me his experience in Chatham. “I go on jogs down 79th street everyday…when I think of Chatham, I’m reminded of community groups, activism, brick bungalows, manicured lawns, and African-American home ownership,” says Jahmal.

This is the narrative about Chatham that tends to get overlooked. Underneath all the stories of violence and crime that have damaged the community, there’s a story of hope and sacrifice from an even larger part of Chatham that’s working to do good and effect positive change.

The diner is an example of that. It’s been in Chatham for over 30 years. Today, however, it’s more than a diner, it’s become a community institution through the efforts of its owner, Josephine Wade — otherwise known in Chicago as Mother Wade.

For as long as Mother Wade has been running this diner, she’s opened up her doors offering food and jobs for anyone in need. There are multiple generations of families whose lives have been deeply impacted by Mother Wade’s outreach, and as she puts it in a recent interview, “there’s not a person that’s on this corner that I haven’t tried to encourage them to either come in here and work or take a job with someone else.”

On the diner walls hangs a portrait gallery of people who have shaped Chicago’s history. And it’s in Mother Wade’s diner where many met to broker deals, organize, and seek political power. You know you’re a somebody when you get your picture hung up next to the likes of Dr. Martin Luther King Jr., Harold Washington, and Aretha Franklin.

Any of our city guides aren’t complete without a closeup food picture. As for the chicken, it stacks up well against any place in town. It’s nicely seasoned, crispy, and when you throw in waffles, well, you got yourself a balanced breakfast.

2. Architecture Tour

After breakfast, Jahmal took me to his block. This is a picture of the community that Jahmal wants to show me. It’s one where neighbors all know each other, there are scores of block clubs, and it’s a picture of a community that watches out for one another. That’s especially the case when it comes to your lawn. If your lawn isn’t looking as nice as it should be, then somebody will surely let you know.

3. Dat Donut

On our last stop, we’re taking a short drive over to Dat Donut, another Chatham landmark that’s been making donuts by hand 24 hours a day, 6 days a week since 1994. The shop is named so because when kids look through the shop’s display case, they say, “I want dat one, dat one, dat one, and dat donut.”

Chicago has seen a bit of a donut renaissance over the past few years, but you’ll be hard pressed to find a Dat Donut regular who’ll tell you of a better donut anywhere else in town. The donuts are rolled, cut, shaped, fried, and glazed by hand every day. It’s that sort of commitment that has given this shop all sorts of local and national press proclaiming just how good their donuts are.

If you’re feeling particularly ambitious, then their donut named the “Big Dat” might be what you need. It’s a giant sized donut about 5x the size of a regular donut, and according to my math, you almost need to order this from just a purely economic standpoint. Any regular donut is $1.05. The Big Dat is $3.35. With it being the equivalent to 5 donuts, the Big Dat comes out to $0.67 on a per donut unit basis. The math is sound. Get the Big Dat. 

As Jahmal and I were walking into Dat Donut, one thing Jahmal pointed out to me was the bulletproof glass you had to order through. Most businesses in the area have it, and they have it for good reason. But he explained that for kids growing up in this community and seeing this everyday, it’s a subtle reminder that “we don’t trust you.” It’s a discouraging message to receive, and for anyone on the receiving end, it has that troubling ability to put limits on one’s own potential.

For many of the kids that Jahmal mentors, this is the only reality that they know. But by taking part in MBMHMC, they have a chance to go on educational field trips, explore all parts of Chicago, and connect with the city. That can be an empowering feeling.

That’s the power of travel that both Jahmal and I have experienced — it has a tendency to unite people, because when we visit each other’s community it’s hard to ignore the goodness and humanity we all share. That’s the lesson I was reminded of when Jahmal invited me to Chatham.