Eyes on the Street: Chicago Bike Couriers of the Nineties

Victor Parrea at 203 North Michigan Avenue, Chicago, late Nineties. Photo: John Greenfield
Victor Parrea at 203 North Michigan Avenue, Chicago, late Nineties. Photo: John Greenfield

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.

Dharma, West Erie Street, Chicago, late Nineties. Photo: John Greenfield
Dharma, West Erie Street, Chicago, late Nineties. Photo: John Greenfield
Harold Smith, North Wacker Drive, Chicago, late Nineties. Photo: John Greenfield
Harold Smith, North Wacker Drive, Chicago, late Nineties. Photo: John Greenfield
Flyer for Bike Messenger Night shows, Chicago, late Nineties. Image: John Greenfield
Flyer for Bike Messenger Night shows, Chicago, late Nineties. Image: John Greenfield
Original Alkaline Trio drummer Glenn Porter, North Wacker Drive, Chicago, late Nineties. Photo: John Greenfield
Original Alkaline Trio drummer Glenn Porter, North Wacker Drive, Chicago, late Nineties. Photo: John Greenfield
Alkaline Trio (and current Blink 182) guitarist Matt Skiba, North Michigan Avenue, Chicago, late Nineties. Photo: John Greenfield
Alkaline Trio (and current Blink 182) guitarist Matt Skiba, North Michigan Avenue, Chicago, late Nineties. Photo: John Greenfield
Chris Mosk and Craig White at a Chicago Cycle Courier Concert at the Fireside Bowl, Chicago, late Nineties. Photo: John Greenfield
Chris Mosk and Craig White at a Chicago Cycle Courier Concert at the Fireside Bowl, Chicago, late Nineties. Photo: John Greenfield
Dabny Santicola, Chicago, late Nineties. Photo: John Greenfield
Abny Santicola, Chicago, late Nineties. Photo: John Greenfield
Jason Neri, Chicago, late Nineties. Photo: John Greenfield
Jason Neri with a tattoo of Pac Man riding an ‘L’ train, Chicago, late Nineties. Photo: John Greenfield
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WCBMA cofounder “Captain” Jack Blackfelt at a Chicago Cycle Courier Concert at Phyllis’ Musical Inn, Chicago, late Nineties. Photo: John Greenfield
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Chicago Messenger Service courier on the Lake Street bridge, Chicago, late Nineties. Photo: John Greenfield
Brantley, Daley Plaza, Chicago, late Nineties. Photo: John Greenfield
Brantley, Daley Plaza, Chicago, late Nineties. Photo: John Greenfield
Kristen Diehl (now Meshburg), by Marina City, Chicago, late Nineties. Photo: John Greenfield
Kristen Diehl (now Meshburg), by Marina City, Chicago, late Nineties. Photo: John Greenfield
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Eric Sward at Tuman’s Alcohol Abuse Center, Chicago, late Nineties. Photo: John Greenfield
333 North Wacker Drive, Chicago, late Nineties. Photo: John Greenfield
333 North Wacker Drive, Chicago, late Nineties. Photo: John Greenfield
Florence Bonneau, Pioneer Court, Chicago, late Nineties. Photo: John Greenfield
Florence Bonneau, Pioneer Court, Chicago, late Nineties. Photo: John Greenfield
WCBMA cofounder Scott "Superdave" Shanahan on North Michigan Avenue, Chicago, late Nineties. Photo: John Greenfield
WCBMA cofounder Scott “Superdave” Shanahan on North Michigan Avenue, Chicago, late Nineties. Photo: John Greenfield
Quaker Tower, Chicago, late Nineties. Photo: John Greenfield
Quaker Tower (now 321 North Clark Street), Chicago, late Nineties. Photo: John Greenfield
Guenevere Nyderek
Guenevere Nyderek, Near East Side, Chicago, late Nineties. Photo: John Greenfield
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Rod Richardson, North Franklin Drive, Chicago, late Nineties. Photo: John Greenfield
Joey "The X Man" Love, Chicago, late Nineties. Photo: John Greenfield
Joey “The X Man” Love, Chicago, late Nineties. Photo: John Greenfield

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  • TonyAB

    Great photos!

  • BlueFairlane

    Believe it or not, I did it for about a year and a half as sort of an early midlife crisis thing about a decade after you took these pictures. Pay was crap, but I still feel like it was the best job I ever had, and I probably would have done it a lot longer if a big health crisis hadn’t knocked me down. I kind-of-sort-of had it in my head I’d write a book about it, but I never did. Craig White, the guy in the sixth picture down who was rocking a sweet silver LeMond, took me out and showed me the ropes my first day.

  • Ben Tre

    When I moved back to Chicago from DC in 1996, one of the first things I noticed was how “normal” the bike messengers looked. In DC, EVERY bike messenger was covered with tattoos and wore a nose ring. Here in Chicago, they looked like a cross-section of the city.

  • johnaustingreenfield

    “I kind-of-sort-of had it in my head I’d write a book about it.” Someone beat you to it. https://www.chicagoreader.com/chicago/shoot-the-messenger/Content?oid=904974

  • Colby Spath

    Amazing. Did this for 2 weeks and went back to waiting tables, lol…

  • BlueFairlane

    That book (plus a lot of procrastination) is one of the reasons I never wrote my own book, though I was going to do a slightly different take on it, more from the view of a 30+-year-old in the middle of all that youth. I think I could have come up with different enough narrative to have landed for a different audience … but then, I didn’t write it, so who knows? I was going to call it “Wrecks in the City.”

  • hopeyglass

    Might wanna hit up John Watson/Radavist for some linkage to spread the word about the predecessors to the hip gunslinging instagrammers of today. Always worth a try to bring people into the advocacy fold, ay?

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