Last Saturday night at Cal’s Liquors, under the el tracks at Van Buren and Wells, bike couriers Brent Olds and Mike Morell sat at the bar sipping bottles of PBR and prepping for the Chicago Loop Criterium.

The course for this underground messenger race, or “alley cat,” was simple: a clockwise, two-and-a-half-mile circuit north on Franklin, east on Lake, south on Wabash, and west on Van Buren. Competitors would complete as many laps as possible in 40 minutes, plus one additional circuit.

Olds and Morell had hatched the scheme on an earlier evening at Cal’s, which is a popular Friday-night stop for couriers. “I was getting mad that there weren’t many alley cats this year,” said Olds, a five-year veteran of the bike messenger business. “So I decided to do it myself.”

A typical alley cat hits a series of checkpoints over a wide area, testing a courier’s ability to navigate pickups and deliveries. But Olds and Morell structured their event as a criterium, in which riders do laps on a short course. “The racers come by every few minutes, so you can have it in a small town and the crowd can get involved,” said Olds. “It’s not like a 75-mile road race where the racers only come by once. A crit is faster and more dangerous than a road race. You’re taking 90-degree turns at 30 miles per hour, so it’s pretty skill intensive.”

Because you need a permit to hold a sports event on city streets and because participants routinely break traffic laws, alley cat races are illegal. Since the Loop Criterium involved a large group of riders circling the same territory again and again, chances of a bust were higher than usual. Nevertheless Olds and Morell were more worried about the safety of pedestrians around the Goodman and the Palmer House Hilton. “But everybody’s a courier and knows what’s up with urban biking,” reasoned Olds. “Everybody’s burned an intersection before.”

Inside the bar, as the Thin Man and his band unpacked their instruments, young men in shin-length cutoffs and Gore-Tex windbreakers filtered in to plunk down the $5 entry fee and sign up with Morell. One of the registrants, Hekter Gonzalez, discussed his strategy. “I’m going to ride hard and try not to run into the pillars,” he said, referring to the steel posts that support the el tracks. “You want to stay inside them but not ride in the middle of the street, ’cause that’s where the potholes are.” He stressed the importance of riding within your limits. “Do what you know you can do–don’t do what you can’t.”

By 9:30 the moonlit night had turned frosty, but a crowd of couriers was drinking at the tables outside and checking out one another’s rides, mostly high-end road racers and single-speed track bikes. The latter, ultralight cycles with fixed gears, usually have no hand brakes, so skidding to a stop on them is an art in itself. The race flyers stated that nonmessengers were welcome to compete, and sure enough, in rolled a posse of civilians–relatively clean-cut bike activists and riders from Critical Mass.

“I’ve never done an alley cat before,” said Yoon Son, who works at the Art Institute. “I’m not nervous–I’m just going to take it easy and have fun riding. The energy of this whole atmosphere is getting me pumped.”

At ten o’clock the 27 racers assembled in an alley across the street from Cal’s, and Olds addressed the group. “Please be careful. No dive-bombing the corners. Don’t take out any pedestrians–it’s not worth it.” He announced that drafting (riding close to a competitor’s back wheel to save on wind resistance) and skitching (grabbing onto a motor vehicle to catch a lift) were legal tactics. “If you get stopped by the cops, tell them you’re just on a ride.” He counted down the start, and the riders took off in a pack, quickly disappearing around the corner at Franklin.

A few minutes later the lead riders whizzed through the intersection of Wabash and Van Buren just a few feet away from Dupree Martin, who was standing on the corner drinking coffee. Slower cyclists brought up the rear, the last few riding at a pace comfortable for conversation. Martin claimed he wasn’t afraid of being hit by the cyclists, although he said one of them had a close call with an el post. “I like to see fun stuff like this in the city.”

As front-runners on their second lap passed State and Lake, the most populated intersection on the course, cops straddling mountain bikes in front of the Chicago Theatre seemed oblivious. But an old man sitting in the window of Dunkin’ Donuts frowned at the high-speed parade.

By the third lap the pack had scattered into small clusters. At the corner of Franklin and Lake they zoomed past the back side of 333 W. Wacker, headquarters of John Nuveen. During the day the building’s steps are a hangout for messengers on standby, but at this hour the area was deserted. The poker-faced competitors looked ghostly in the amber glow from the lights under the el. They banked sharply around the corner, then bunny-hopped over a two-inch-deep pavement cut that stretched across Lake.

Back at Cal’s, Olds tried to keep track of how many laps each rider had completed, while beer-drinking spectators hooted and hollered encouragement. Four fans, including a couple of black-clad goth kids, stood in the middle of Wells Street and corked the southbound car traffic while cyclists raced west through the intersection.

After 40 minutes, Olds shouted “last lap” to the riders who passed by the tavern. One circuit later, Nico West, a lanky fellow with wire-rim spectacles, zoomed across the finish line with arms outstretched, then glided to a stop in front of the cheering crowd. He had completed five laps.

“It was hell,” said fourth-place finisher James Pray. “There were so many intersections to go through, and the way everybody was busting lights was so fucking ugly. I don’t like blazing through the lights–I don’t like pissing cars off. Nico’s just a badass, too. He’s strong, intense, and hyper as hell. He bursts through everything pretty good.”

Hekter Gonzalez was the only racer to take a spill. “I was one of the top five following Nico,” he said. “He cut off a car, and then I tried to go around it. My pedal hit the floor as I was turning. I flipped, landed, and hit my head. I’m very glad I was wearing a helmet. My side is fucking hurting. My elbow is fucking hurting. I’ll find out if I’m scraped up after I take my clothes off. I’m just glad I didn’t get hit by a car.”

The first woman to cross the finish line was Nicole Kemerer, who works at the March of Dimes. “I thought I was in last place,” she said. “So I wasn’t even going very fast. I ride like a grandma–I stop at all the red lights. When Brent Olds told me I was in first place, I thought he was lying.”

When all the competitors were in, bikers and spectators gathered on the sidewalk outside the bar for an awards ceremony. Olds announced first-, second-, and third-place winners, as well as the winners in the female and fixed-gear categories, with each getting a percentage of the pot. Afterward the group hung out and chatted under the tavern’s pink-and-orange neon sign.

Suddenly the screech of automobile tires and a terrifying boom split the night. A westbound Geo Prism had run a red and smashed into a southbound Mitsubishi Galant, sending it hurtling southwest toward the sidewalk. The driver of the Mitsubishi steered to avoid the crowd of bikers, crashing instead into a line of parked cars in front of the tavern. Airbags activated, and the motorists walked away from the accident, dazed but OK. Both autos looked totaled; they smoked and bled their vital fluids into the sewer. The dozen or so bikes locked up by the curb were unscathed.

“I think the car accident was some weird thing of karma,” said Olds. “The race was a definite success with no serious injuries. Then this happened right afterwards. It was almost like an exclamation point.”

Art accompanying story in printed newspaper (not available in this archive): photos/Saverio Truglia.