Court Battles, COVID, And Collateral Damage: A Year Of Drama For Chicago’s Tamale Guy

On April 24, 2020, 54-year-old Claudio Velez sat in his living room and cried. On the table next to him sat a cease-and-desist letter from the City of Chicago, a white sheet of paper signaling the end of his decade-plus legacy as Chicago’s Tamale Guy—or so he thought.

What’s still unclear is how Velez got in hot water with the city, who exactly found his tamale-selling objectionable, and why. The answers may lie in a multi-front cold war among Chicago’s powerful and tumultuous neighborhood organizations—and their fractured and often fractious Facebook groups.

But even that drama has been eclipsed by a snowballing legal fight with Velez’s would-be partners, who Velez claims took advantage of his incapacity due to a COVID diagnosis to try and launch a restaurant built around his popularity and recipes while cutting him out of the business. The story has led Velez and his friends on a journey through several Chicago neighborhoods as those areas change with the times—for better or worse, depending on who you ask. With some rare exceptions, Velez himself isn’t talking publicly, to the media or anyone else. He did not respond to initial requests for an interview for this story, though his son Osmar Abad Cruz said via phone that his father is lately getting over his longtime media shyness.

I first met Velez back in 2008 when I was 24, testing new shots with the bartender at Inner Town Pub in Ukrainian Village. Velez walked in with his eponymous red cooler, shouted “tamales,” and the whole room erupted. Suddenly people everywhere were throwing up bills, calling over the Tamale Guy for an order like you’d yell for a hot dog at a ballgame. “Cheese, chicken, or pork,” Velez would ask. You’d hand over five bucks and get six fresh, hot, homemade tamales to soothe your drunken hunger pangs.

By that time Velez was already Chicago royalty. Bargoers tracked his location on Twitter. Chicagoans dressed up like him for Halloween, and everyone wanted their picture with him when he showed up to their favorite spot. Bartenders actively tried to get him to come sell his tamales in their businesses.

photo credit: Kim Kovacik

Alongside Velez’s rise to fame, the West Loop neighborhood was becoming more and more homogenous. Residents who lived there before it began to gentrify remember factories, butcher shops, a red-light district—and a proliferation of inexpensive food like tacos, empanadas, and pickled vegetables.

“The West Loop was awesome at one point; it was really cool,” says Moshe Tamssot, admin for the True West Loop neighborhood Facebook group. “It was like the backwater of Chicago. No one really knew about us.”

As more transplants and companies looking for cheap space moved to the area from highly gentrified neighborhoods and the suburbs, they began to complain about the industrial feel of the neighborhood.

“The little taquerias and the little diners started disappearing … [and] we were starting to become more and more homogenous,” Tamssot recalls. “Our tacos would get smaller, they would get prettier, and they would get more expensive.”

photo credit: Kim Kovacik

Soon enough, the West Loop evolved into what it is today—an expensive, in-demand neighborhood with stylish restaurants and all-night patio parties. The residents argued among themselves about all things West Loop, creating different factions. Tamssot started the True West Loop Facebook group in 2016; a splinter group unhappy with his management of the group started the Real West Loop group in 2018. Two other groups already existed—the West Loop Community Organization and the West Central Association. There’s another group as well, called Neighbors of West Loop. The groups continue to spar with one another over the neighborhood’s direction and character.

In March 2020, COVID came to Chicago, and the Tamale Guy struggled. Gone was the opportunity to make money hawking tamales to local bars, which were all closed. Gone was his main source of income. Velez partnered with Keith Palmer, who works in the special events industry in Chicago, to organize a tamale event in the Sherwin-Williams Paint parking lot in Lakeview. Customers preordered tamales by the dozen. Velez made the tamales, brought them over, and customers picked them up in the lot.

The tamale event netted Velez about $2,000, but as an undocumented immigrant, he was also exposing himself to risk. So instead of another public event at a specific location, he went underground. Palmer shared his own phone number online, and people would text or call looking for tamales. He’d then share Velez’s number, they’d place their order with him, and Velez would deliver tamales to their homes. “He didn’t want to get in trouble with the city,” Palmer says.

In April 2020, Velez hooked up with Tamssot, who runs the West Loop Community Garden in addition to his Facebook group. As reported by Eater Chicago, they put together two tamale pick-up events at the garden. Customers ordered online, paid through Venmo, and picked up tamales in socially distant garden events. The first event earned Velez $1,650, and the second got him another $2,445.

photo credit: Kim Kovacik

Despite working within city requirements and those of the Chicago Police Department, Tamssot claims the other neighborhood groups still disapproved of the events. Soon after the second event and before a planned third tamale sale, Velez and Tamssot both received cease-and-desist letters. All told, the city received eight complaint calls and several complaint emails about the tamale sales. But Tamssot claims this was not really about tamales at all. “We were subject to a coordinated attack from a competing Facebook group,” he says.

Twenty-Fifth Ward Alderman Byron Sigcho-Lopez, who represents the West Loop, believes Tamssot is correct. He told Eater Chicago that Velez received one letter, while Tamssot received five—four about permits the events didn’t nominally need, and only one about tamales. Tamssot was the target, Sigcho-Lopez told Eater Chicago, and Velez was just caught in the middle. Tamssot recently noted in his Facebook group that the proposed bureaucratic sanctions against the community garden and Velez have since been rolled back.

For his part, Tamssot is still frustrated that Velez got swept up in the neighborhood feuds. “Look what you did to the Tamale Guy,” he says. “Look what you did to him. I mean he’s an old man, [and] he’s crying at home. They call him collateral damage. You can’t fucking call a guy [collateral damage]. This isn’t a war.”

Regardless, Velez’s cease-and-desist letter was strong enough to spook him. Every day Velez or someone associated with Velez continued to sell tamales without a real commercial kitchen, he could be fined between $200 and $1,000. So, the Tamale Guy parted with his namesake food.

News of the cease-and-desist broke in early May 2020, and the Tamale Guy’s fans were incensed. Chicago rallied around their tamale hero. Within what seemed to be minutes, a GoFundMe campaign to help with his everyday expenses went up. It pulled in more than $10,000 in less than six hours. All told, the campaign earned $36,000. It was enough money for Velez to realize a longtime dream: opening an official Tamale Guy restaurant.

photo credit: Kim Kovacik

Tamale Guy Chicago opened in Ukrainian Village in August 2020. Velez had spent weeks picking out the right business partners, eventually landing on Pierre and Kristin Vega, a local chef and his wife who had been Velez’s friends for about ten years. The first few days in business, the restaurant had lines for blocks and was selling out of tamales within an hour. It seemed like a dream come true for an immigrant and his vision—until Velez got COVID.

Not even two weeks after the restaurant opened, Velez landed in the hospital with severe coronavirus. He was put on a ventilator and stayed in the hospital for 35 days. Tamale Guy Chicago closed when Velez was diagnosed, but the Vegas reopened after about two weeks and continued to run the business in his absence.

Meanwhile, another GoFundMe campaign emerged, this time for Velez’s medical expenses. It was organized by Kristin Vega because Velez doesn’t have health insurance. The GoFundMe raised almost $57,000. Velez recovered in October 2020 and went to take his rightful place at Tamale Guy Chicago’s helm.

But there was a problem. While Velez was in the hospital, the Vegas allegedly hatched a scheme to push him out of the business. Velez claims they took his recipes and ran the restaurant with them, and when Velez tried to come back to work, they informed him there wasn’t room for him. If Velez tried to work there at all, the Vegas intended to sue him, Velez told the Chicago Tribune at the time. His family members that worked there before were no longer allowed on the premises. Velez says the Vegas insisted that there were no profits, and that they didn’t owe him anything.

photo credit: Kim Kovacik

Velez (whose legal last name is Velez-Gonzalez) filed a lawsuit against the Vegas in March 2021. The filing requested the Vegas immediately stop using his name and recipes, and pay him the money he’s owed from the 50-50 split of profits they agreed on when they opened the restaurant. The Vegas denied any wrongdoing at the time. Reached for comment, the Vega’s attorney supplied the same statement as given elsewhere in the media: “The Vegas vehemently deny all of the allegations asserted by Mr. Velez-Gonzalez, and are confident the facts will bear out in their favor. They look forward to resolving this matter soon.”

“It’s infuriating,” says Paulo Villabona, general manager at Folklore Chicago and a Tamale Guy fan of many years. “I’ve seen this guy for 20 years. We used to have this running joke because we thought Claudio could be in multiple places at once. We even thought about creating a comic book about him like he had a superpower. He was all over the place. He was constantly hustling. It seemed like such a great story to see him get his own brick and mortar place and see his dreams fulfilled and everyone was so happy about it. … It seems like this never-ending drama for this guy and I think it makes people pull for him even more. I mean how many jumps will this guy have to make just so that he can work in his own business?”

The battle over the original Tamale Guy restaurant in Ukrainian Village is still raging; the next court date is July 29, and then another in August. Per a court call on June 22, Tamale Guy Chicago is closed for business. There’s a cash obligation of more than $150,000 in order to get out of the five-year lease.

With Tamssot’s help Velez secured a new location in early July for his eponymous restaurant. He’ll be partnering with Lone Wolf, a neighborhood tavern on Randolph Restaurant Row in the West Loop. He and his family have been teasing developments regularly on the renewed Tamale Guy Instagram. Clearly his own expectation, and that of his fans, is that this partnership proves more equitable and beneficial than the previous one. He remains media-shy and isn’t talking to the press much about his plans either way.

“This is the story everyone wants to see a happy ending to, otherwise it’s like why do we all work so hard if we can’t realize the dreams we have,” Villabona says. “There are very few compelling stories like this one for the community, and I would find it difficult for anyone not to root for this guy to come out on top.”

Tamssot agrees that Velez deserves to finally enjoy the success he’s worked so long and hard to achieve. “If this happens,” he says, “it would be the ultimate American Dream story.”