Charlie Wheeler was walking south on Rush Street Tuesday morning as I turned the corner from Chicago Avenue, heading north toward the Newberry Library. On his head, a gray beanie with an orange propeller. For all the cartoons I've seen featuring guys in pinwheel hats, I'd never had the chance to actually speak with one before. The exhibit on the influence of immigrants on printing in Chicago would have to wait.
"Do you mind if I take your photo for the Chicago Sun-Times?" I said. Wheeler did not.
He is 68, from Crown Point, Indiana, and has been in the propeller beanie business for six years. Before that? "A little bit of everything," he said. How does one get into the pinwheel hat trade?
"Somebody gave me a baseball cap," he explained. "I don't wear baseball caps — the visor gets in the way. So I removed the visor, and looked at it a minute."
Inspiration struck.
"And then I thought, 'Oh no! I know what that needs,'" he said.
The typical pinwheel beanie, Wheeler said, is a shoddy affair. His creations sell for $40.
"There's a very high end hat," he said.
Juan Bolanos came hurrying over, a big grin on his face.
"Are those for sale?" he asked. Wheeler admitted they are.
"I usually charge $40," he began, slipping into his salesman's patter. "But as you seem to be a working class guy, so I'll take 25% right off the top bringing it down to a paltry $30."
Bolanos, manager at Devil Dawgs across the street, laughed.
"You don't have a solid black color?" he asked.
Wheeler did not.
"These things are hilarious," said Bolanos. "I love it."
"This is the closest I have," said Wheeler, producing a two-tone gray.
"Does it have a brim?" Bolanos asked.
"No, a classic propeller beanie."
I hoped the pinwheel hat might have originated in Chicago. As a center for the American toy industry in the mid-20th century, the city is the birthplace of numerous novelty items, including wind-up chattering teeth and fake vomit.
Alas, the propeller beanie was invented in 1947 by Ray Faraday Nelson, a Michigan teenager who attended science fiction fan conventions and created it as part of his spaceman costume. Though Nelson would go on to write his first novel, "The Ganymede Takeover," in collaboration with sci-fi icon Philip K. Dick, Nelson insisted that inventing the propeller beanie was his claim to fame. "I think it's probably my best bet of being remembered," he said, presciently.
By 1948, the hats were a widespread youth fad, and quality must have been an issue, because that year Walgreens advertised offering "the best ones" for only 39 cents.
Wheeler's destination Tuesday — which he asked me not to specify — prompted me to wonder whether selling propeller beanies on the streets in Chicago is legal.
"I have a peddler's license," said Wheeler, who commutes in on the South Shore Line, $7.50 round trip with the senior discount. "The city of Chicago peddler's license fee is $100 for two years."
And if you're thinking, "No wonder the city is broke," the fee is deliberately kept low to assist those struggling to get by. "It's supposed to help people get a leg up on things," Wheeler said.
Even with the license, knowing where selling is permitted is an issue. Chicago police are not too busy to ticket a man hawking propeller beanies in the wrong place.
"The entire business district is a non-peddler zone," Wheeler said "There are so many nitpicky rules and regulations and different places you can and cannot peddle."
Bolanos looked inside the hat.
"Would you take $20 for it?" he said.
"That I cannot do," Wheeler replied.
After the sale fell through, Bolanos urged Wheeler to ramp up his online presence.
"You should get a TikTok," he said. "That stuff will catch on so quick."
Wheeler's hats can be found on eBay if you plug in the word "wisillianagan." Otherwise you have to catch him on the street, about once a week, as he revels in being here.
"I love Chicago," he said. "In all my wanders, I never felt unsafe. I just love the city."
Wheeler said he's walked as much as 15 miles to sell fewer than 10 beanies. "Eight or nine would be a really, really, really good day," he said. "Usually it's nowhere near that. I smile when I sell three."
Charlie Wheeler smiled Tuesday — selling three hats in six hours, he told me later when I followed up by phone.
"That means I get to eat and still have a few dollars in my pocket," he said.
