New Book Explores What It’s Like Working as a StreetWise Magazine Vendor

Bridgette Adu-Wadier | June 26, 2025, 6:42 pm

Whether you find it on street corners or outside the grocery store, StreetWise magazine has been a staple in many Chicago neighborhoods for decades.

For the people who sell copies of the magazine, it’s more than just a job. It’s often their way out of challenges such as poverty, homelessness, substance abuse and mental health issues.

Now, vendors are telling their own stories in a new book called “Who We Are: Stories From the Chicago StreetWise Community.”

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The book is a collection of first-person narratives from several StreetWise vendors who discuss what it’s like selling magazines and the various obstacles they had to overcome to gain stability. Evanston Township High School student Anthony Mateos, the book’s author, interviewed several StreetWise vendors about their experiences and compiled them in an oral history.

Many StreetWise vendors build relationships with their customers and the neighborhoods they sell in. Mateos said the vendors add a unique human element to print media, making it an iconic aspect of local Chicago-area culture.

“I know that they [the vendors] are a fundamental column of the Chicago community,” Mateos said. “So many people know their own vendors in their neighborhoods where they live or maybe in the Loop where they work. No matter if it’s in the harsh Chicago winters or maybe a heat wave, they’re always out selling the magazine and being happy while doing it.”

The weekly magazine launched in 1992 with a business model aimed at benefiting vendors, who purchase copies of the weekly magazine for $1.15 and sell them for $3. They keep all of their profits and get access to food, toiletries and mental health resources provided by the organization. Copies are sold by 150 trained vendors.

The magazine covers a wide array of topics, ranging from sports to social issues.

Growing up, Mateos had frequent encounters with vendors and would visit the old StreetWise headquarters in Uptown with his mom.

“There’s one vendor that I encountered a lot; his name is Alonzo,” Mateos said. “He still is around today working for StreetWise. He’s still so happy after some 10, 15 years. He just has such pride and joy for working under the publication, and it motivated me and inspired me to write this book.”

A StreetWise vendor who goes by A. Allen has been with the publication for 15 years. He sells magazines on weekdays in front of the Mariano’s at Sheridan Road and Foster Avenue. He said StreetWise empowered him to overcome his addiction to drugs and alcohol.

“I was addicted to alcohol and drugs, and I finally got clean for a year,” Allen said. “I wanted to keep my sobriety, so when I came to StreetWise it was a way up and out of drug addiction and alcoholism. The way I used StreetWise was that every time I would think about alcohol or drugs, I would go out and sell magazines.”

After experiencing homelessness for three years, Allen said his work as a vendor has allowed him to gain more financial stability.

“It [StreetWise] means the ability to be an entrepreneur and navigate my own life,” Allen said. “StreetWise offers a lot of opportunities to be self-employed or to be your own boss. I get to choose where I want to sell, what times I want to sell and how long I want to stay out to sell the papers. That’s very important to me.”

All of the sales from the book go to StreetWise. Mateos said about $1,500 has already been raised. See where to buy a StreetWise magazine here. Cash, Venmo and Paypal payments are accepted.

Read an excerpt from the book below:

The cover of “Who We Are: Stories From the Chicago StreetWise Community” by Anthony Mateos

Higher Powers

Dre

Vendor

I learned about StreetWise when they first came out. I was homeless. The magazine cost 25 cents for me, and then it sold for a dollar. It wasn’t a magazine; it was a paper. I remember it was advertised on the news saying they come out with StreetWise to help homeless people have a sense of employment and keep from begging.

I became a vendor because I saw it as an opportunity to have employment. Let me tell you the truth about it. At first, I thought it was an easier way to get money so I could get drugs. This is in ’94, something like that, when StreetWise first came out. I was an addict back then and a chronic alcoholic. I wanted an easy way to get money instead of just beg. And when StreetWise first came out, people was very generous with their donations.

But StreetWise, they helped me. They gave me resources. See, I don’t do drugs no more. Right now, I’m in tune with my higher powers. I’m in AA.

StreetWise is a very resourceful place to be. StreetWise helped me pay my bills. It helped me get something to eat. It helped me to meet people. It helped me to feel good about myself. That’s what StreetWise has given me.

StreetWise gave me clothes. They give me food. They give me companionship and friendship. They give me advice. They helping me find an apartment right now. Rashawn was teaching me motor skills on the computer.

They give me happiness, like when they have parties. Like on the 30th anniversary for StreetWise, that was sweet. It was packed in here. We had the back door open, the front door open. It was a beautiful thing.

I’m a veteran. Right now, I work for DoorDash. I’m about to get me some StreetWise today. It’s working out cool. I make about a hundred a day.

So, I do my DoorDash, and I sell my magazine. One day I made more with StreetWise than I did with DoorDash.

The most thing I love about DoorDash and StreetWise is I can choose my own hours. Ain’t nobody on my back. And StreetWise, if they have it, they will help you. Just like now, I’m here getting help for affordable housing because I got Section 8.

Okay, let me tell you this. I love my StreetW/ise staff, and they love me. They already know I’m gonna come in to laugh and join in. Especially Ron, when he sees me coming through the door, he’s like, “Oh my Lord, who brought the cat in?” Julie would be like, “Hey, Dre, where you been? How you been doing?”

I told you, I’ve been here since they opened. I know everybody, and you know what? It hurts me when people leave. The staff, just like Rashawn, I came to see him today. He gone; he found another job.

I shift around sometimes. I sold StreetWise out on the West Side. I sold out on the South Side. I even sold in Bolingbrook. I’m not going to go to Humboldt Park because I don’t speak Spanish.

What challenges? The weather and panhandlers are the main two challenges that I face. The rain don’t help. The rain don’t help at all. It’s the rain that’s the challenge, because if it’s cold outside, I still sell. If it’s snowing outside, I still sell. If it’s sunny and hot outside, I still sell.

Selling StreetW/ise is a challenge in itself. It ain’t got nothing to do with the neighborhood. Every neighborhood in the world got some prejudice in it. And me being 60 years old, I already know this. I have people used the n-word on me and tell me to get a job. Nah, ain’t no different challenges in no neighborhood. Only challenge I have is when it takes me too long to sell my magazines. In any neighborhood, that’s my only challenge.

One of my spots is Portillo’s around 600 N. Orleans Street. If I establish that spot for, say six months, I got regular customers there. They see me, they’re buying magazines, give me a fat tip and everything. But if I go there and there’s another vendor there, I say, “Man, what’s up?” That causes a problem because I done established that spot for six months straight. Literally working every day for six months at a certain time. But I don’t fuss or fight about it. I got people there that I see every day. We more like friends.

One guy Venmo’d me $100. I never forget that. He bought the magazine and Venmo’d me $100. Oh, and this lady, she gave me $100. She just came around the corner and gave me five 20s. There’s a lot of people out here that have it like that.

Now I got me an apartment I had for two years, And, um, I’m a widower. My wife used to work here too. My wife died in 2011. We used to work at Portillo’s because they got two doors. She’d be on one side; I’d be on the other side.