On April 19, about 40 people gathered under the Locust Street bridge, arriving down a steep hill to a graffiti-covered slab of concrete. Some were Milwaukee locals, others arrived via Amtrak from Minneapolis or biked from Chicago.
Bikes were strewn about the muddy gravel path. People smoked cigarettes, drank warm beers, and hunched over sheets of paper that would dictate their afternoon. After five years of hiatus, the Milwaukee Messenger Invitational (MMI) alleycat race was resurrected this Easter weekend.
The MMI has officially been around since 2002. A version of the race took place in 2001 during Bastille Days, though its name is lost to time. Wayne Wallner, who founded Milwaukee’s Breakaway Courier company in 1998, said he was certain that it included the word “massacre.”
Nonetheless, the MMI had happened annually every year, before the COVID-19 pandemic brought things to a halt. As an alleycat-style race, the MMI is both unsanctioned by the city and has strict rules. Riders are required to complete what is known as a manifest: visit checkpoints in any order (although some have time limits), collect signatures, and return it by the end time. And of course, they must travel everywhere by bike.
This year’s return of the MMI was organized primarily by former bike messenger Steve Bostwick—though he’s quick to say the race wouldn’t have happened without help from many volunteers, both familiar faces and new ones. Bostwick said his goal was to have riders experience “the life of a messenger” in all its chaos.
One of those volunteers, Brett Huber, explained the MMI this way: “It’s notorious. There is no f-ing around.”
At one checkpoint, I met Chad and Diane, both former bike messengers, now volunteers. When I asked Chad why the MMI had started, he explained that Minneapolis had their own annual alleycat (Stupor Bowl) and that Milwaukee wanted to start their own, so they did—a lighthearted Midwestern rivalry.
But the MMI also pays homage to Milwaukee’s history of bike messengers—back in the 1890s, legend has it that Gregory Steichen began working for the Western Union telegraph company on his bike. The building is now the Swingin’ Door Exchange at 219 E. Michigan St., and a stop for the MMI this year.
In the early ’90s, there was a large demand for messengers, who would deliver things like airplane tickets, legal filings, and blueprints. It was a vibrant, thriving community. These days, Kyle Lewis, who works at Breakaway, says they deliver things like catering orders, bank deposits, and the occasional legal filing. They work year-round, no matter the weather, armed with a two-way radio and messenger bag.
It would be hard to deny that Milwaukee’s bike messenger business has faltered in the years since MMI began. The internet has replaced many of the tasks messengers once did—there are no more paper airline tickets to deliver. Still, Lewis said he’s glad to be “carrying on the legacy.”
“I hope there will be a renaissance,” he said.
Under the bridge, riders listened attentively as Bostwick explained the rules before the race, scribbling down notes. Then—with little pomp and ceremony—riders were off, scrambling up the hill of the embankment with their bikes on their shoulders.
Tasks this year took riders all the way to Milwaukee’s west side, through downtown and up to the East Side. The first checkpoint was at Milwaukee Public Library in Washington Park, where riders had to look up a book by its ISBN number, find page 57, and write down the first sentence of paragraph three on that page. (One book was Deadeye Dick by Kurt Vonnegut.)
For their second checkpoint, riders were given a second manifest at MKE X BIKE, which included a stop at Kazube’s Park, with scenic views of Jones Island and the distinct feeling of a liminal space.
And lastly, to Uptowner in Riverwest—an MMI staple—to complete as many miniature delivery routes as possible. There was even a cargo leg: pedal a bale of hay to a destination and back.
Of course, the alleycat was not without frustrations for riders. There were wipeouts, lost manifests, broken chains. Despite this, riders persevered for the sake of free beer and food.
Henry, from Minneapolis, said his favorite part of the race was wandering into a bar playing the Bucks game while looking for a checkpoint and asking anyone if they would sign his paper. He eventually figured out it wasn’t a checkpoint when he was met with blank stares. Asked to sum up his experience, he said it was “hard in a really intriguing way.”
“There’s nothing quite like this. It’s six hours of as much as you can handle.”
Rowdy, a messenger from Chicago, griped about the hills but was grateful to make new friends and “see a hint of the culture” as he rode through different neighborhoods.
The shared suffering and exhaustion created a sense of brotherhood and sisterhood that was palpable, and integral to bike messenger culture. At one point, when a rider’s bike broke down, Huber offered to ferry him to a bike shop via a cargo bike. As Chris Zito, owner of MKE X BIKE, put it: being a bike messenger means you “have a couch to sleep on anywhere in the world.” It’s a subculture that welcomes everyone.
The MMI drew spectators too, with some stopping me to ask where all these cyclists were headed. James Graham, of Louisville, Kentucky, said he found the event on Instagram and wanted to be a part of the action. A self-proclaimed fan of alleycats, he cheered on the racers as they arrived with manifests to be signed.
When all the points were totaled up, Nikki Munvez was the first-place winner of the MMI this year, hailing from Minneapolis. Her secret to winning? Listening to the directions.
At the start of the race, Bostwick had pointed out a former messenger named Cherry, and said his signature was worth a point. Munvez collected more signatures from Cherry than anyone else. Upon winning, Munvez was elated.
“This was unbelievably fun. I am shocked I won. I love Milwaukee so much!” she said, beaming. She added, “Come to Minneapolis and take the Amtrak!”
Wallner, who made an appearance at Uptowner’s patio after the race, looked around at the racers as they shared chili and cigarettes.
“It’s exciting to see a new generation,” he said with a proud look on his face.
Want more Milwaukee Record? Subscribe to our free weekly newsletter and/or support us on Patreon.