How This 1950s Lemonade Stand Became an Agent for Change

Food is more than what’s on the plate. This is Equal Portions, a series by editor-at-large Shane Mitchell, investigating bigger issues and activism in the food world, and how a few good eggs are working to make it better for everyone. ​​ 

“There’s going to be a sugar shortage,” says Mario “Skip” DiPaolo, sitting on the front stoop of his West Taylor Street townhouse in Chicago’s Little Italy. “But I know a guy.” After a long day of picking up supplies in his truck, the 74-year-old owner of Mario’s Italian Lemonade rubs his sore knees and waves to customers waiting to place orders at the window of his family’s frozen lemonade stand. “I got lemons today, too.” During the first heat wave of summer, Chicagoans stand under a shade tree strung with plastic lemons, spooning slushy treats served in waxed paper cups.

Founded in 1954 by DiPaolo’s father, Mario Sr., who immigrated to Chicago from Italy’s Abruzzo region, the lemonade stand was a modest expansion of a hobby intended to keep his son out of trouble. The younger DiPaolo started at age six with an old-fashioned hand-crank machine on a cart outside the family’s general store, where he sold frozen lemonade for two cents. “We don’t call it ice,” DiPaolo explains. “It’s Italian lemonade. That’s just the name we’ve always stuck with.” Back then, a horse-drawn wagon delivered ice in hundred-pound blocks, and lemon juice was squeezed by hand before churning. “My grandma bought me my first electric lemon squeezer with S&H green stamps,” says DiPaolo. “[She] taught me how to make change [by] playing Monopoly with real money. And she cheated! A great lady, I loved her dearly.” According to DiPaolo, his grandfather, father, and uncle built the permanent stand out of salvaged wood. When the business took off, they bought motorized Alaska Hostess freezer machines and added more flavors (now they offer about 30). The most popular is peach, but only when the fruit is fresh. Customers regularly stop to ask DiPaolo when it will appear on the specials menu.     

Not everyone loves the tri-color stand, with its fanciful lettering by Galileo Scholastic Academy fourth graders. As the Near West Side neighborhood gentrified around the University of Illinois Circle Campus, many of the original Italian-American residents were displaced by the end of the 1960s. The family business was targeted as an eyesore and a nuisance. DiPaolo says that he spent years resisting threats of closure. Suffice to say, it got political in a specific Chicago way. He admits that he and one of his sons have been in “a little trouble.” Two police cruisers drive past, lights flashing, but shortly after, a couple of young officers line up for lemonade, too.

Street vendors across the U.S. have faced a long history of targeted harassment. In Chicago, Department of Sanitation inspectors regularly threw their products in the trash or doused them with bleach. A viral video of NYPD officers arresting a woman selling churros from an unlicensed cart in the subway sparked outrage in 2019. It happened again last month, when NYC Parks Department security threw away churros during the Mermaid Parade on the boardwalk at Coney Island. And in greater Los Angeles, where permitted sidewalk vending was legalized in 2020, food sellers still continue to be verbally abused, racially profiled, handcuffed and detained. 

Even children who set up lemonade stands in their front yards risk fines and citations, except in the 14 states where permits aren’t required. “Leave the little kids alone,” says DiPaolo. “You don’t want to take the starch out of them when they’re just getting started.” Advocacy groups have emerged to address the imbalances inherent in these micro-entrepreneurial businesses: The LA Street Vendor Campaign holds community forums, assists with permit applications, and provides funds to offset the economic impact of pandemic lockdowns. Manhattan-based Street Vendor Project offers outreach such as immigration resources, legal counseling, small business training, and loans. Asociación de Vendedores Ambulantes supports work-with-dignity causes, and continues to promote food cart regulation and health standards in Chicago.

The light is fading, and the breeze slows, so cheerful whirligigs fashioned from recycled bleach bottles dangling above the stand stop swirling. The staff is still scooping orders. “If you’re a good worker, and you can make change, you got a job here,” says DiPaolo, whose family donates to St. Ignatius College Prep High School‘s tuition assistance program. “We hire high school kids that can stay on their feet. Because I go in there and I’m too slow now. For most of these kids, though, it’s their first job. And you always remember your first job.” Offering up the citrusy treat of summer often goes hand-in-hand with serving community. Maybe it’s just a few bucks in their pockets, but it can also be a change agent, and an early way to teach budding entrepreneurs about social good. 

DiPaolo nods at the last customers lingering around the stand. A father and his three adult children pause outside the townhouse fence to greet him.

“You’re the man!”

“Hey, how you doing,” DiPaolo replies.

“I’ve been bringing my daughters here since they were about five.”

 The son chimes in.

 “My name is Mario, too.”

  “No kidding. I don’t owe you money, right?” DiPaolo jokes.   

“It’s the guy who comes every day for 20 years, he made this business successful. Not a movie star who comes once and mooches lemonade.” He sighs and gets to his feet, ready to head inside for dinner. “I should be retired. I should stop.”

Chicago will be slightly less chill when he does.

Please consider donating to Alex’s Lemonade Stand Foundation for Childhood Cancer.