Even in the heyday of the bike messenger business in the late 1980s — when an estimated 1,500 couriers zoomed around the streets of the Loop — there were fears the fax machine could end the need for fast, in-person deliveries.
Then the internet came roaring along in the 1990s and 2000s, destroying even more of the bike courier business. The industry shrank to a few hundred by 2007.
When the COVID-19 pandemic hit, shutting down most in-person office work downtown, it created the largest existential threat to bike couriers since the industry launched.
But the pandemic, while brutal, wasn’t a death knell to the courier business as some had worried. Instead, it adapted to changing consumer habits, couriers told the Chicago Sun-Times. Food deliveries actually grew, and the industry is still attractive to customers who need to maintain a chain of custody for documents as well as those looking to save money when compared to car deliveries.
And the anti-driving culture tied to the community — which had its own distinctive fashion and promoted a punk, do-it-yourself lifestyle — is still prevalent. Even as only three registered companies remain in Chicago and the number of messengers has dipped to about 50, some couriers say they have stayed in the business because of that tight-knit community, the flexible nature of the job and improving working conditions.
“There is a sense of camaraderie,” said 40-year-old Chris Spillane, of Pilsen, who works for U.S Messenger in the Merchandise Mart. “Everyone knows everyone.”
Dylan Jackowiak, also a courier at U.S. Messenger and a Pilsen resident, said the community extends to other states.
“There are messengers in cities all across the U.S.,” said Jackowiak, 30. “If I wanted to go to New York for a bike race or something, I know who to hit up to get a place to stay.”
‘We were formidable’
Decades ago, bike messengers were so ubiquitous that they wielded a level of political influence and were often vilified in the media.
Comet Messenger Service owner Jim Sailer, 81, said his company used to have so many messengers that he had a shed for them to park their bikes near 13th Street and Michigan Avenue.
Sailer purchased Comet in 1979, three years after the company was founded. He remembers the “halcyon days” of the business between the 1970s and early 2000s, when his company delivered papers for five of the 10 top law firms Downtown and also made deliveries for the insurance, auto, industrial and pharmaceutical industries, among others.
“We were formidable,” Sailer said.
Back then, the messenger business was collectively big enough that it had its own association to wield political influence in Springfield and the city.
“We lobbied with the city and the state over parking, loading zones and other things,” Sailer said.
In the late 1980s, the first accounts of bike messengers in the Sun-Times often reflected sentiment from drivers and pedestrians as hundreds of couriers on any given day raced around and between cars on streets with far fewer bike lanes than now. City Council members and then-Mayor Richard M. Daley sought to regulate an industry they considered out of control.
“Too many pedestrians are being knocked down, pushed aside and seriously hurt,” Daley, according to Sun-Times reporting then, said in 1991 — before he signed an ordinance regulating the industry one City Council member dubbed a “nuisance.”
The ordinance mandated couriers wear helmets and vests that displayed a messenger’s company and registration number.
John Greenfield, who worked as a bike courier for several companies from 1992 to 2001, remembers police occasionally cracking down on the helmet law.
“Back then, it was so old school that I didn’t even have a walkie-talkie. The dispatcher gave me a bunch of quarters and I would call him from pay phones,” said Greenfield, who is now editor of Streetsblog Chicago.
Greenfield was a paper messenger, delivering envelopes, mailing tubs, blueprints and the occasional bankers box of documents. Almost all of his work was in the central business district, between Roosevelt, Division, Halsted and the Lake.
Greenfield remembers the bar Rossi’s, “which is still exactly the same as it was,” and the now-closed Cal’s Liquors at Van Buren and Wells as places couriers often met after work — as they still occasionally do.
Phyllis’ Musical Inn on Division Street held a weekly messenger night, when bands featuring couriers would play. The punk band Alkaline Trio played some of its earliest gigs at messenger night, Greenfield said. Guitarist Mike Skiba and original drummer Glenn Porter were both couriers.
Messenger night was also where, Greenfield said, Chicago Critical Mass co-founders Jim Redd and Michael Burton first considered their idea for monthly rides from Daley Plaza — which still draw hundreds or thousands of cyclists today.
Still, animosity toward bike messengers continued, especially after authorities accused one of shoving a Loop commuter to his death down the stairs of Union Station.
“Fatal incident bruises bike messengers’ image,” a Sun-Times headline read on Dec. 17, 1999.
The relationship with the public seemed to improve somewhat a few years later when Daley proclaimed Oct. 7, 2007, to be Bike Messenger Appreciation Day. A proclamation signed by Daley states there were 300 couriers working for 17 companies then.
When the pandemic hit
COVID-19 hit the courier industry hard.
“It was devastating,” Sailer said.
His business relied on office workers Downtown. With nearly everyone staying home, he laid off all of his nearly 20 bike messengers.
Jackowiak recalled sitting around the offices of U.S. Messenger waiting to be dispatched. Lounging around “was fun for about a week. And then it was like, ‘Oh man, my paycheck, my poor paycheck,'” Jackowiak said.
He found work at a bike shop. And his co-worker, Spillane, started delivering for Cut Cats Courier — which already had a foothold in food delivery and actually saw business boom at the time.
“All the restaurants we worked with got busier and busier with deliveries,” said Margot Considine, 38, a bike messenger for Cut Cats. “We picked up clients. Kind of the opposite experience of other courier companies.”
More recently, competition from food-delivery apps such as GrubHub, DoorDash and Uber Eats has caused that market to shrink again.
‘Not like Amazon tossing a package in a lobby’
The Downtown office occupancy rate still hasn’t recovered — currently around 23% of Loop offices are vacant — but the messenger companies that survived over the last few years say cost is a big reason: It’s cheaper to pay a biker for a Loop delivery than for a car. It’s $20 for a biker to deliver something in less than 30 minutes, Spillane said, compared to in some cases triple that cost for a driver.
Some businesses also prefer couriers to preserve a “chain of custody,” including getting a signature for important documents, Spillane said.
“This is not like Amazon tossing a package in a lobby,” he said.
Jackowiak said on any given day he might deliver freshly printed menus to a restaurant, a roll of historical construction blueprints, or carpet and tile samples sent from the Merchandise Mart to design firms.
Courier culture
Even as their number shrank, an international “courier culture” persisted, messengers said.
Messengers still hold “alleycat” bike races in which couriers from around the globe compete in unsanctioned street races that simulate the rigors of a typical workday. Couriers described them as their version of a business conference, where couriers network and talk shop and race other competitors for prizes.
That was the case for Jackowiak, who traveled in April to race in the Milwaukee Messenger Invitational and slept on the floor of a fellow messenger’s home.
The courtesy goes both ways. Jackowiak said his apartment building hosted about 20 other couriers a few years back for the Chicago Cuttin Crew Classic race.
Those races are not held as often as they were during the heyday of the industry, couriers said. The underground events garnered public scrutiny in 2008 when a courier was killed in a Chicago race.
Still, the races are a sign of couriers’ commitment to the job — and lifestyle.
“Someone would probably think you’re nuts for [paying to] travel and re-create a day at work,” Spillane said.
Future of work
One outcome of the declining business has been the rise of worker-owned courier companies, and the shift from working for commission as independent contractors to being on the payroll with benefits. That’s the situation with Cut Cats, which is now the largest courier in the city with a staff of 40. Couriers for U.S. Messenger and Comet are also classified as workers.
“It’s good to be an employee,” Jackowiak said.
Cut Cats Courier is trying to diversify its business as it struggles to compete with food delivery apps.
“We’ve talked to bookstores, T-shirt companies, but nothing has panned out,” he said.
Jackowiak said he believes the courier business has been squeezed as much as it can.
“To be still doing this is kind of crazy. But I think we’re down to the core business that can’t be replaced,” he said.