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Pilsen, Little Village, West Loop

‘Mayor Of Maxwell Street’ Charlie Joe Henderson Kept Order At Iconic Market — And Never Missed A Day

Charlie Joe Henderson, who died at 81 last month, worked the old Maxwell Street market, which he fought to save, and the new version.

Charlie Joe Henderson succeeded as a businessman both in and out of Maxwell Street. He died late last month at 81.
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NEAR WEST SIDE — Charles Henderson remembers the years he spent on the original Maxwell Street fondly. 

Henderson would set up the vending tables first thing in the morning, meticulously organizing 8-track tapes and cassettes for ease of browsing. Groups of musicians would play on the street around him. For most of those memories, he was with his father, Charlie Joe Henderson, nicknamed “the Mayor of Maxwell Street.”

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Charlie Joe Henderson posing with a camera.

Charlie Joe Henderson was well-known around the market from the ’70s and beyond as a man who not only sold music, but rented tables to vendors, settled disputes and was committed to making the market the best it could be. The businessman died Jan. 22. He was 81. 

Before Charlie Joe Henderson joined the vendors on Maxwell Street, he had many business ventures on the West Side, where he lived most of his life, his family said. He had been working in a garment factory when he decided to open his first shop at 8 S. Pulaski Road in 1963, said his wife, Marie Henderson. 

“One morning, we were sitting at the table talking and he said, ‘Marie, I’m tired of pushing the clock for somebody else. I’m going to open my own business,’” Marie Henderson said. 

Charlie Joe Henderson had an eye for photography and an ever bigger knack for business, so he opened a photography studio on Pulaski, his family said. 

After that, he and his wife opened stores along West Madison Street selling 8-tracks, cassettes, LPs and 45s. They were some of the only — if not the first — Black store owners on the street, Marie Henderson said. 

Marie Henderson said her husband was “a man of vision” who knew when to pivot. 

“He never let anything send him down. His mind was always active in doing something, thinking of stuff,” Marie Henderson said.

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Charlie Joe and Marie Henderson at one of their stores, Out of the Past Records.

Charlie Joe Henderson started selling music on Maxwell Street in the ’70s, but he didn’t buy tables to rent to other vendors until the ’80s, his son said. 

It was Charlie Joe Henderson’s role renting out tables and resolving disputes over vendor placement that earned him a reputation as a “mayor” of sorts, said Steve Balkin, of the Maxwell Street Foundation. 

Balkin, a professor emeritus of economics at Roosevelt University, said he was researching the economic benefits of the Maxwell Street market in the early ’90s when he met Charlie Joe Henderson. 

“A mayor governs a city, and part of governing is collecting taxes and providing services. … Another element is to resolve conflict,” Balkin said. “That’s what Charlie was doing. He was providing these essential functions.”

The location of vendor tables was important because an ideal spot at the market meant you might be able to sell more, Balkin said. 

“There would inevitably be conflict,” he said. “Vendors would joust with each other.”

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Charlie Joe Henderson and his son Charles Henderson at the new Maxwell Street market.

Charles Henderson said he recalled times when he, his father and others would come together to settle disputes between vendors diplomatically.

“He wouldn’t stand for violence,” Charles Henderson said. 

After going on for nearly a century, the Maxwell Street Market ended in 1994, transforming into University of Illinois at Chicago parking, sports fields and condos. The city set aside a nearby block for a new market, but only 400 out of 1,200 vendors followed, Balkin said. Only 20 sold at the most recent market. 

Credit: Colin Boyle/Block Club Chicago
A placard recognizes the former Maxwell Street Market in University Village on Feb. 16, 2022.

Charlie Joe Henderson was outspoken in his disappointment over the original Maxwell Street Market being forced to close, his family said. He wrote a piece in the Chicago Defender in 1994 to make a case for the market to remain. 

“Should a city sell its citizens, its birthright, its heritage, its landmarks and institutions in the name of progress?” Charlie Joe Henderson wrote. “Never may that happen! These are things that can never be replaced or duplicated.” 

The full text from Charlie Joe Henderson’s piece in the Chicago Defender.

Charles Henderson said he and his father were there on Maxwell Street the day the market closed for good. The market went from spanning eight blocks to just half of one.

“It was horrible,” Charles Henderson said.

Despite the downsizing, Charlie Joe Henderson continued vending and renting tables at the new Maxwell Street market on Canal Street until he got too sick to do so in 2018, his son said. 

At the original and new market, “he never missed a day,” Marie Henderson said. 

“Rain, shine, sleet, snow, you could always count on him with the tables,” she said.

Charlie Joe and Marie Henderson’s music store, Out of the Past Records, remains at its original location: 4407 W. Madison St. One of their granddaughters is taking it over to keep it in the family.

Credit: Colin Boyle/Block Club Chicago
Old buildings line Halsted Street surrounded by modern development in University Village on Feb. 16, 2022.

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