Eyes on the Street: Chicago Bike Couriers of the Nineties

This post is a little off-topic for Streetsblog Chicago, but we thought our readers would appreciate a glimpse of what the downtown bike delivery scene was like 20-plus years ago. All photos in this post are the copyrighted property of photographer John Greenfield and may not be used for commercial purposes without express permission from the photographer.

I was a bike messenger in Chicago on and off for several years in the 1990s and very early 2000s, starting in summer 1992, when pay phones were still common in our city and a dispatcher sent me out with a pocket full of quarters in lieu of a walkie-talkie. Needless to say, times have changed quite a bit during the last quarter-century. Traditional envelope-and-mailing-tube messengers haven’t completely gone the way of the dinosaur with the rise of digital communications. But at least as many couriers on the street nowadays are delivering food, as on-demand culture becomes more dominant.

I shot the following images while messengering in the late-Nineties, mostly between late 1996 and 1998. Those were some of the most active years for the Windy City Bike Messenger Association, a loose confederation of couriers that a few of us launched after being inspired by the summer 1996 Cycle Messenger World Championships in San Francisco.

The WCBMA’s main activities were publishing the courier ‘zine “Dead Air” (I hope to post copies of these online in the not-too-distant future), organizing informal messenger-style races called “alleycats,” and hosting concerts showcasing bands with couriers in them. The latter included the weekly “Messenger Night” series at Phyllis’s Musical Inn in Wicker Park. The still-active punk band Alkaline Trio played some of their earliest (and sloppiest) gigs at Messenger Night, and it was also the place where Chicago Critical Mass cofounders Jimm Redd and Michael Burton first met over $1.25 bottles of Busch and hatched their scheme for monthly rides from Daley Plaza.

I hope the portraits below, most of which I shot with disposable cameras from Walgreens, provide a sense of what it was like pushing paper in Chicago during the pre-smartphone age, or bring back fond memories of that era if you lived through it. More snapshots of that scene, of varying quality, are available here and here. If you have additional info or corrections regarding the people and places in the pics — or other retro Chicago courier photos you’d like to share — please post them in the comments section or contact me directly at jgreenfield@streetsblog.org.



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