Street Smart Chicago

Checkerboard City: Gangster Rap

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Lorena Cupcake Caiazzo/Photo: John Greenfield

By John Greenfield

In a Midwestern town where folks dress conservatively, Chicago bike style icon Lorena Cupcake (her legal middle name) Caiazzo stands out like a handful of Skittles scattered across the Wall Street Journal. Easily spotted by her candy-colored outfits, rainbow-and-lollipops tattoo and messenger bag emblazoned “Cupcake Gangster,” she’s also an astute commentator on the local cycling, drinking and foodie scenes via her frequently updated, often hilarious Twitter feed, @lorenacupcake.

But Caiazzo, twenty-five, is far from just a hipster gadfly. A frequent participant and volunteer at “alleycats,” underground messenger-style checkpoint races, she runs the bike event Twitter calendar @chicagoholdup and helps stage the annual Bicycle Film Festival. Last year she and a few other petite fixed-gear enthusiasts formed Tiny Fix, a bike gang especially for women under five-foot-two-inches, which organizes bar nights, dance parties and now their first alleycat. The Tiny Fix Ace Race happens Saturday, May 26–visit for details. 

I recently caught up with Caiazzo, fresh off her day job as a bank teller, over $3 cheeseburgers at the Blue Frog, a messenger bar at 676 North LaSalle in River North. She gave me the skinny on Tiny Fix, the upcoming race, and the things she loves and hates about biking in Chicago.

What’s your involvement with the local bike scene?
I’m just a girl who kept showing up. I kept going to events until I knew everybody, and that’s it. As far as getting into a more proactive role and throwing events, what happened was I was joking with some friends about starting a bike gang. There’s KC Winter, Karen “Kaz” Altes and Anna Titcomb. And we were like, “Oh, we’ll be the tiny girls on fixed-gears gang.” To my surprise we didn’t just joke about getting knuckle tattoos, we actually built a website, had a bar night and started getting involved with people.

Lorena Cupcake Caiazzo/Photo: John Greenfield

We want everyone who rides bikes in Chicago to have more fun. It’s not about a certain group or only the cool kids. We want to make fun shit happen. Two, we want to make the world a friendlier place for female cyclists, specifically, petite female cyclists. I really hope that someday somebody running a bicycle company or a bicycle apparel company finds Tiny Fix and says, “Holy Shit, there’s all these girls out there who are under five-foot-five inches who ride bikes and would buy our products if we actually made them their size. If you’re under five-foot-five inches or have to ride a 47cm frame or smaller, your options are really limited.

Do you race in alleycats?
I don’t do speed races because I’m not that badass. But I have worked checkpoints at multiple Downtown Shakedown races. I have ridden the Sadie Hawkins ride. I raced in PolCat. I checkpointed Wrigley Dash. If I have a friend who’s throwing an alleycat and I don’t want to race it, I always offer to checkpoint it.

Tell me about your upcoming alleycat.
The Tiny Fix Ace Race is an alleycat that absolutely anyone can have fun at. It doesn’t matter if you are the world’s fastest messenger who knows the Chicago grid like the back of your hand, or if you have the creakiest, busted-ass Schwinn cruiser from 1963, you can still race this race to the best of your ability, win a ton of prizes and have a ton of fun and feel challenged at the same time. There is a speed race, which is a traditional alleycat. You’re going to be racing about twenty-five miles in two hours, and the fastest person wins.

There’s also the Poker Ride, which is a ride of about ten miles in two hours. It’s no pressure, and you don’t have to run any reds or act real crazy. You just have to hit five checkpoints and collect a playing card at each one. And then at the end of the race whoever turns in the best poker hand is the winner. So it’s more about luck and having fun and hanging out and participating than it is about who’s badass. It’s not a dick-measuring contest.

Lorena Cupcake Caiazzo/Photo: John Greenfield

I was a messenger in Chicago for six years, a long time ago, but the current alleycat scene flies totally under my radar. How do people hear about the races?
It’s all Facebook. People try not to publicize things too much because they’re illegal.

What’s your favorite thing about biking here?
The people. Sometimes I can ride my bike into work and I’ll see four different friends, also riding their bikes. My boyfriend’s a messenger and that’s how I met him. I wouldn’t have ever met my best friend if I hadn’t met him at the Bicycle Film Festival, so I love the way biking brings people together.

Lorena Cupcake Caiazzo/Photo: John Greenfield

What would you like to see improve?
I want all the grated bridges covered. That’s my big pet angry. They’re not fun on a bike with skinny tires. I think they’re a safety hazard and I would much rather see every grated bridge covered than another inch of protected bike lane go in. I just think it’s a higher priority. I know it’s an engineering thing because some of the bridges can’t carry extra weight, so it’s not as easy as slapping steel plates on them. But if the city is really serious about making improvements to bike infrastructure, I want to see that fixed.

I’d also like to see more people doing what Tiny Fix is doing and throwing events. Anybody who has a bike, an Internet connection and a group of friends can be making awesome stuff happen.

Lorena’s List: the Cupcake Gangster’s favorite Chicago folks, bikes, bags, threads, drinks, eats and cakes.

Lorena’s List: The Cupcake Gangster’s Windy City faves

I really admire the Cycle Messenger World Championships crew. Those kids have been throwing events in Chicago since I moved here and there are a number of women involved who are every bit as integrated as the men. There’s Christina and Allison Peck—they’re twins—and Nikki Munvez. They’re super-badass.

Bikes for petite women
Decent ones? Jamis, Fuji and Wabi make fixed-gears that are forty-seven centimeters or smaller, and I wish I could afford a Gunnar Street Dog—it’s an awesome option. There are girls out there who are smaller than me for sure, and I really don’t think they should not be allowed to ride bikes or be forced to ride some kid’s Huffy because they’re short.

My messenger bag’s made by Seagull Bags, out of Columbus, Ohio. I love them.


Sock it to Me makes the world’s best knee socks. PF Flyers make really awesome sneakers that have a stiffer sole than Converse, and I think they’re more stylish and I just like them way better for bike riding. Thrift stores. Maxwell Street Market is great for really ridiculous cheap club wear that you can haggle with the guy over. I got this lime-green crop top with silver lamé cheetah print on it.

Drinks (biker bars)
Blue Frog on LaSalle on Thursdays for the $3 burgers. There’s always a group of messengers here chomping on cheap burgers and shooting the shit with Cliff, the bartender. There’s Cal’s Liquors downtown, any day of the week but especially Mondays because it’s $2 PBRs. If I get out of work and I don’t want to ride home yet I go to Cal’s. Handlebar, especially for the vegans. Boiler Room—it’s $7.50 for the PB&J–that’s a slice of pizza, a PBR and a shot of Jameson. For people who burn a lot of calories, eat a lot and drink a lot, that’s a good deal.

I’m not vegan, but my best friend is, so I go to Dharma Garden for affordable, BYOB Thai food which is either vegan or not. When I want to go fancy, I love Longman & Eagle. There’s Original Rainbow Cone in Beverly. You ride your bike for fifteen miles and then eat this ice cream cone and it’s the best ice cream cone you’ve ever had because you just rode your bike fifteen miles, just for ice cream.

The Flirty Cupcakes truck is great because they saw my messenger bag and they were like, “Hey, you, that’s awesome.” And then I showed them my I.D. that shows that my legal middle name is Cupcake. And they’re like, “Alright, free cupcake for you, Cupcake.”


The Green Line: upcoming meetings, rides and other sustainable transportation events

Bus Rapid Transit in the Twenty-Fifth Ward Learn about potential BRT projects coming to the ward and provide input about public transportation needs in the community. Thursday, May 24, National Museum of Mexican Art, 1852 West 19th, (312)427-3325 x392,, 7pm-8pm; free.

Chicago Critical Mass Join hundreds of cyclists for this monthly bike parade and demonstration for bike-friendly streets, for a leisurely pedal to a destination yet-to-be-determined. Friday, May 25, Daley Plaza, 50 West Washington,, 5:30pm; free.

Hockey Nostalgia Ride This tour of hockey landmarks includes the United Center, the UIC Pavilion and Johnny’s Ice House plus a lunch stop at the Palace Grill, decorated with Blackhawks artifacts. Saturday, May 26, Waveland Clock Tower, 3701 North Lake Shore Drive, (773)262-0031,, 8:30am-1pm; free.

Bicycle Tour of Uptown Join forty-sixth ward Alderman James Cappleman and Bike Uptown on a tour of the neighborhood including the Peace Garden, Montrose Peninsula and Essanay Studios ending at Big Chicks restaurant and bar. Saturday, May 26, Uptown Bikes, 4653 North Broadway, (312)636-3066,, 3pm-4pm; free.

Bike the Drive Some 20,000 cyclists will take over Lake Shore Drive for several hours during this annual car-free benefit ride for Active Transportation Alliance. Sunday, May 27, Columbus Drive and Jackson Drive, (312)427-3325,, start 5:30am-7:30am.

Women and Trans Night West Town Bikes hosts this weekly open shop session strictly for female and trangender folks who want to work on bikes in “non-patriarchal” surroundings. Wednesday, May 30, 1147 North Campbell, (773)772-6523,, 7-10pm; $10/hr suggested donation.

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