The storied career of Wendell Williams, from breaking into broadcast to retirement

Wendell Williams holds up copies of the latest Street Sense edition at the Takoma Park Farmers Market in Maryland on Aug. 4. Photo by Jack Walker

It’s Sunday morning in Alexandria. Vendors are loading tubs of produce into their cars and heading for the neighborhood of Del Ray. Soon, they will prop up colorful tents that throw into relief the gray sky overhead. Like the others, Wendell Williams begins his morning with a drive to the farmers market, traveling fifteen minutes west of his residence in Prince George’s County.

Once there, Williams settles into his usual spot on the sidewalk. The neighborhood’s farmers market straddles two sides of the street, and Williams places a stool right in the middle of foot traffic. He pulls out a milk crate containing copies of the latest edition of Street Sense, plus a sign that reads: “Support jobs for the poor and those experiencing homelessness!”

Shoppers begin to stroll in, many of whom Williams greets by name. He trades quick jokes with those who buy a copy of the paper, and even tosses dog treats to his four-legged visitors. Within view from the market, a local Black church called First Agape Baptist Community pokes above the tent tops. Williams once lived in an apartment above the church, which is how he first discovered the market years ago.

“I started in this market by helping the farmers set up,” he said. “And then I would go leave and sell my papers.”

Eventually, Williams realized he could sell papers at the farmers market instead of going into the District, which was further away and already covered by other vendors. He has been a regular at the market ever since, and said his success there has inspired other weekly stops outside the city, like another farmers market in Takoma Park.

Wendell Williams (far right) at ski promotion in 1976 with WTUE FM colleagues.
Photo provided by Wendell Williams.

Williams is a native Washingtonian, but his decades in the street newspaper scene started outside the District. He began his career in broadcast sales and marketing, and spent decades working in radio in the DMV, Ohio and Michigan with organizations such as WTUE FM in Dayton, WXCD FM in Detroit and WFOG FM in Norfolk. But in the 1980s he began to struggle with addiction and mental health issues, ultimately falling out of both the industry and long-term housing. He moved through shelters and short stints and friends’ houses, winding up at a Cincinnati shelter called Drop Inn Center in 1996.

Wendell Williams in Detroit in 1991 during his time with WXCD FM out front of Motown.
Photo provided by Wendell Williams.

During this time, Williams began volunteering with the Greater Cincinnati Homeless Coalition. That’s where he met the team behind a local publication called Streetvibes, who encouraged him to sell their paper as a vendor. He took the job on and found his background in marketing came in handy, securing $300 in his first few hours of sales.

When Williams returned to his native Washington, D.C. years later, he parlayed his success selling newspapers into a position with Street Sense, becoming one of the publication’s earliest vendors. He takes pride in the fact that his employee badge number is in the double digits, making it one of the first given out.

In 2016, Williams also began writing for Street Sense, one year later launching his own column called “Random Acts of Kindness.”

“It was very important to me to chronicle the nice things that perfect strangers did for me during and after my journey of homelessness,” he said. “The whole premise of my column was to remind people that the nice things we do for perfect strangers could be crucial to their existence or their survival.”

Wendell Williams throws a treat for local dog Bubblegum at the Del Ray Farmers Market in Alexandria, Virginia on Aug. 17. Photo by Jack Walker

Williams said that people who have never experienced housing insecurity often do not realize the impact their actions can have on individuals struggling with homelessness.

“To us, it could be just, ‘Hey, I just did something nice here, and I keep on with my life and totally forget about it,’” he said. “But I still remember things people did for me 27, 28 years ago when I was in the midst of homelessness or addiction.”

Over the next seven years, Williams penned 29 columns reflecting on moments of generosity he encountered in his day-to-day life. He continued writing and selling papers even as he secured long-term employment.

From 2018 to 2020, Williams served as a peer counselor for individuals struggling with opioid addiction in Arlington. Then, in 2020, he became a case manager for people experiencing homelessness with the Prince George’s County Department of Social Services.

“I helped them navigate the Prince George’s County social service system to help them access services that they need to move away from their homelessness or prevent them from falling into homelessness,” he said.

Williams is one of many DMV residents whose experiences with housing insecurity inspired and informed a later career in advocacy work surrounding homelessness. For him, experiencing firsthand the struggles his clients have faced made advocating for their needs more intuitive.

“I pretty much have focused the last six years on people who have mental health and substance abuse issues,” Williams continued. “I’m able to do that from the basis of using my own lived experience from being homeless myself and recovering.”

Throughout this time, Williams continued to work for Street Sense, and said it has provided a supplement to his income through major life changes. In days of financial hardship, he said working as a vendor has meant the difference between “living on the McDonald’s extra value menu” and having the choice of a higher-quality meal.

“Selling the paper allows me to have Chipotle every now and then, in terms of a metaphor for life,” he said. “If I want Chipotle I can have it, versus being stuck.”

Wendell Williams holds up copies of the latest Street Sense edition at the Takoma Park Farmers Market in Maryland Aug. 4 Photo by Jack Walker

Williams is currently in the midst of another career shift, retiring from his position as a case manager. But he said he did not have a full say in departing from the role, as his supervisors chose not to renew his contract. He believes it ultimately came down to a personality difference with management.

In part, Williams thinks that has something to do with his involvement with Street Sense and his advocacy work. He was traveling through South Carolina and Georgia with a friend in 2022 when they learned there was a hurricane forecast and that they needed to evacuate. While they got out of the region safely, it pushed Williams to think about weather emergency procedures in place within the District for people experiencing homelessness.

He called several different county agencies in the D.C. region, including his own social services department in Prince George’s County, to inquire about whether they had emergency policies like these on the books.

To his surprise, he said many did not have plans for how to support people experiencing homelessness during extreme weather events like hurricanes. He wrote about his experience and the need for proactive policies like these in a column in Street Sense, but said the scrutiny on county agencies upset some of his colleagues.

After years of advocating for and working with those in need, Williams said he hoped for a retirement that was celebratory or exciting. Instead, he found his final days of work for the department lackluster.

“It was unceremonious,” he said. “I didn’t get a luncheon. I didn’t get any cards.”

For now, Williams said he is getting used to retirement, and still has his newspaper sales to lean on. While Williams has maintained his role as a vendor over the years, he stopped writing for Street Sense in 2022, citing editorial differences with the paper’s previous leadership. But with his newfound free time, Williams said he hopes to start writing regularly again, largely because he sees a need for the gratitude and positive thinking his column brought in the past.

Plus, Williams said his column helps readers understand they can make an impact in the lives of people experiencing homelessness in small ways, too.

“I need to remind people that when you see that homeless person out there, you don’t have to do this big thing that changes their life totally,” he said. “Maybe it’s just the kind of thing at a moment that reminds that person that they are still human.”

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