In the late 1980s, Chicago’s bike messenger industry thrived, with approximately 1,500 couriers navigating the bustling streets of the Loop. However, as technology advanced, fears of obsolescence surfaced, first with the advent of fax machines and later the internet, which dramatically diminished the courier workforce by 2007, leaving only a few hundred messengers in the city.
The COVID-19 pandemic posed a new existential threat, decimating in-person office work in downtown Chicago. Despite the turmoil, the pandemic did not spell disaster for the courier industry. Instead, it prompted adaptation to shifting consumer behaviors; food deliveries surged, and demand for reliable document handling persisted.
Many customers sought couriers to maintain a chain of custody for important documents, favoring their services over car deliveries due to cost efficiency. The cultural identity of the cycling community—a blend of distinctive fashion and a punk, do-it-yourself ethos—remains strong and fosters camaraderie among the remaining couriers.
Chris Spillane, a 40-year-old cyclist employed by U.S. Messenger, captures the spirit of this community. “There is a sense of camaraderie. Everyone knows everyone,” he remarked.
His colleague, Dylan Jackowiak, highlighted the national nature of this community. “There are messengers in cities all across the U.S. 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,” Jackowiak explained.
The industry had once wielded substantial influence, especially within regulatory circles. Jim Sailer, owner of Comet Messenger Service, recalls a time when his company enjoyed significant business dealings with major law firms and other industries. In the height of the industry, Sailer could park his messengers’ bicycles in a dedicated shed at Michigan Avenue and 13th Street.
“We were formidable,” Sailer reminisced. The collective power of couriers led to the formation of an association that lobbied for favorable terms regarding parking and loading zones in the city.
In the late 1980s, sentiments toward messengers began to sour, with public concern over safety as cyclists zipped through crowded streets with fewer bike lanes. Chicago officials, including then-Mayor Richard M. Daley, sought to regulate the industry due to rising incidents involving messengers.
They implemented an ordinance mandating couriers to wear helmets and conspicuous vests displaying their company name and registration number. John Greenfield, who worked as a bike courier during the ’90s, recalls working without modern technology. “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, now the editor of Streetsblog Chicago.
Much of Greenfield’s work involved delivering envelopes, blueprints, and documents across the central business district. The tight-knit community of couriers would often congregate at local bars post-work, including favorites like Rossi’s, which remains unchanged today.
Aside from social bonds, bike messengers fostered a vibrant culture that included music. Weekly messenger nights at Phyllis’ Musical Inn were common, with live performances featuring bands that included members from the courier community.
Despite the close-knit relationships forged, animosity towards bike messengers persisted, particularly after a tragic incident whereby a courier allegedly caused a commuter’s death. Media coverage often depicted messengers in a negative light, showcasing public frustration with their behavior on the roads.
However, some recognition came with a proclamation from Mayor Daley in 2007, designating October 7 as Bike Messenger Appreciation Day, acknowledging the 300 couriers then working in the city.
When COVID-19 struck, it wreaked havoc on the messenger industry. Sailer described the situation as devastating, with office workers—who comprised the bulk of his clientele—staying home. As a result, he was forced to lay off nearly all of his bike messengers.
U.S. Messenger’s Jackowiak echoed similar sentiments, where he and his colleagues experienced a sharp decline in work. “Lounging around was fun for about a week. And then it was like, ‘Oh man, my paycheck, my poor paycheck,’” he lamented.
For some, the pandemic provided a pivot; Jackowiak later found employment at a bike shop, while Spillane transitioned to Cut Cats Courier, which had already tapped into the growing food delivery market. Margot Considine, a bike messenger at Cut Cats, noted that business thrived during COVID-19 as restaurant clients increased their delivery demands.
As restaurants adapted to the new normal, the competition from food delivery apps like GrubHub, DoorDash, and Uber Eats began to cut into traditional courier work.
In the aftermath of the pandemic, the downtown office occupancy rate languishes around 23%, but surviving messenger companies assert that their services remain a cost-effective choice. Hiring a courier costs significantly less than using a car delivery service, providing an attractive option for businesses seeking timely deliveries.
Spillane emphasized the importance of their service. “This is not like Amazon tossing a package in a lobby,” he argued.
On a typical day, Jackowiak could find himself delivering anything from freshly printed restaurant menus to historical blueprints, highlighting the diverse nature of courier tasks amidst the changing landscape.
Even as the number of messengers dwindled, a global ‘courier culture’ has endured, as couriers engage in alleycat races to demonstrate their skills and foster community. These unsanctioned events serve as opportunities to network and develop professional ties, representing the industry’s spirit.
Jackowiak recently participated in the Milwaukee Messenger Invitational, and expressed the benefits of sleeping on the floor of a fellow messenger’s home.
These races illustrate the dedication couriers have to their work and lifestyle, even if they seem unconventional to outsiders. Spillane remarked, “Someone would probably think you’re nuts for [paying to] travel and re-create a day at work.”
The evolution of the business model in the courier industry has led to the rise of worker-owned companies. Many couriers have transitioned from being independent contractors to employees receiving benefits, marking a significant shift in labor relations within the industry.
Cut Cats Courier, the largest courier company in the city with 40 staff, continues to explore avenues to diversify its operations amid competition from food delivery apps.
Jackowiak noted that attempts to branch into new areas, such as partnerships with bookstores or apparel companies, have yet to yield tangible results.
Despite the challenges, he remains optimistic about the industry’s future. “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 concluded.
image source from：chicago
