“One Pioneer, a Thousand Riders” by Oboi Reed


Oboi Reed at the new wooden velodrome at 8615 S. Burley – photo courtesy of Reed

In September John interviewed Oluntunji Oboi (“O-bye-ee”) Reed about his efforts to launch The Pioneers Bicycle Club as a way to get more South Siders and African Americans involved with cycling. Last month, Oboi did his first Chicago Critical Mass ride. We invited him to submit the following write-up of his experience for Grid Chicago:

In the words of The Notorious B.I.G., “It was all a dream.”
I dreamed of cycling as a form of healing.
I dreamed of cycling consistently with family and friends.
I dreamed of forming The Pioneers Bicycle Club.
Dreams came true, then I kept dreaming.
I dreamed of riding in Chicago Critical Mass.
I dreamed of riding in Chicago Critical Mass through some parts of the South Side.
The dream of riding in the mass came to life on Friday, October 28th, 2011.
The dream of riding through parts of the South Side, well, that dream is a bit more complicated.


The mass assembles at Daley Plaza – photo by RansackedMuse

It all started a few weeks before the October ride. I decided to ride in Critical Mass for the first time. Dreamer that I am, I considered proposing a route for the ride that would cover some parts of the South Side – perhaps a ride through the historic Bronzeville community or the vibrant Hyde Park neighborhood.

My mind was made up. I was most definitely riding in the mass. What was I to do about creating a South Side route? I had no idea. So, I reached out to the Chicago Critical Mass listserve for suggestions on how to create a route. Several riders responded with support for the ride. They offered suggestions on a route and points of interest along the way. I reached out to John Greenfield and Steven Vance from Grid Chicago. John offered a number of suggestions for creating a route map. He put me in touch with Willow Naeco, the editor of The Derailleur, a Critical Mass magazine. Willow was amazingly supportive and offered resources to bring the route map to life. Many more offered support and suggestions, such as Anne Alt, president of Friends of the Major Taylor Trail.


Photo by RansackedMuse

I had made up my mind to do a South Side route and I was determined to do it. There was still one challenge. I started working on the map on Thursday and the ride was the next day. I opened Google Maps and began. After only a few minutes, I knew this task was bigger and more complicated than I had imagined. I worked on that map for hours. I worked mightily to move the route past Occupy Chicago and through parts of the South Side, ending at The Chainlink Halloween Party in Lincoln Park, all while keeping the route to a reasonable distance. I finally came to the realization that I was not going to complete a route map in time for the ride. I reached out to John and Willow to share my challenge. They continued to support the effort, doing all they could to assist me in getting a map completed in time. I appreciated the help. However, it was late and I decided I was done.

I didn’t create the map in time and I was hurt. I felt I had let myself down and I let down the many other riders who supported the idea of a South Side route for the mass right from the beginning. I felt like I missed a golden opportunity to energize cycling on the South Side of Chicago. In the midst of planning for the mayor’s protected bike lane network and bike share system, it felt like the time was now, and I missed it.


Photo by RansackedMuse

I went to sleep Thursday night thinking, screw it, I won’t even ride in the mass. I woke up Friday morning thinking I have much work to do and I am just getting started. There was value in the journey of suggesting a route and working on a map. I decided to find the lesson in the experience!

Renewed, I rode in Critical Mass, and it was an amazing experience. There were over a thousand riders. We owned the streets. Our streets. The energy was electric and there was joy in the air. We took off from Daley Plaza going toward Jackson & LaSalle.

This was the Halloween ride and many riders were dressed in costumes. Someone was dressed in a full gorilla outfit and was handing out bananas to onlookers. Going down LaSalle we rode up on a driver who was clearly pissed that he couldn’t cross LaSalle due to the mass. The gorilla approached the man in the car and sincerely offered him a banana. The man, in turn, waved him off and yelled out, “Get the f— outta here!” I laughed so hard, I almost fell off my bike


Critical Mass rolls past City Hall – photo by Bob Kastigar

As we approached Occupy Chicago, the energy was building up. And, then BOOM! It all exploded in an orchestra of drums, chants, bells, screams, high fives, salutes, and much, much more. Critical Mass riders showed their support for Occupy Chicago and Occupy Chicago showed their support for Critical Mass. It felt great.

The mass rode on. We snaked in a westerly and northerly direction, going through the West Loop, River North, Wrigleyville, Lincoln Park, and other communities. All throughout the ride, some bystanders were not happy but most pedestrians and drivers respected the mass and simply waited it out. In the Gold Coast an older couple attempted to walk through the mass instead of waiting for the mass to pass them by. One of my fellow riders yelled out “Make way for the wealthy, make way for the wealthy!” Many of us laughed out loud.


Photo by Brent Knepper

After two hours of riding we were rolling south on Michigan Avenue, approaching Wacker Drive. I thought to myself, perhaps we can keep straight on Michigan and go South all the way to 35th & King Drive, because that intersection represents the heart of Bronzeville for me. I also used to work at a Bank One branch on that corner. It would be the closest and best location to memorialize my ride to the South Side.

Then the mass turned right on Wacker so I picked up my pace to reach the front of the ride. I asked several riders at the front of the ride about going South to 35th & King Drive. Some were fine with the ideas and some were not. No one wanted to make the decision on it, since Critical Mass is supposed to be a leaderless ride, but in a way we were all leaders.

The mass rode on. We were back on LaSalle headed toward Occupy Chicago for the second time. I continued to make my case for riding to Bronzeville. I eventually developed a rapport with a rider in a yellow hoodie. I suggested it to him, as he seemed to be one of several people at the front of the ride who were setting our course. He said that most people in the mass live on the North Side and we had been riding for so long that 35th & King Drive was too far away. He explained that if we started going South at this point, many riders would leave the ride and head back North. I disagreed with the gentleman and told him so. I mentioned to him the South Side needs love too! I was disappointed. For me, it was a chance at redemption, since I did not complete the route map for a South Side route as I intended.


Photo by Flipped Out

The ride ended at Michigan & Congress, circling Occupy Chicago several times. I stopped to take a breather, I thought about what to do next. It felt there was unfinished business to attend to. Perhaps I could suggest to a few riders that they keep going south with me. I stayed quiet. Perhaps I could ride south by myself. I thought about it for some time. With no decision made, I hopped on my bike and headed south on Michigan Avenue. I was still thinking. I was still dreaming of a South Side route for CCM.

As I rode, I finally decided to ride to the corner of 35th & King Drive. I was alone. It didn’t matter. I rode on. It was not easy. I, along with the entire mass, had been riding now for nearly three hours. I was only at about Roosevelt Road on Michigan Avenue. And, I realized the gentleman in the yellow hoodie was certainly correct. It was indeed too far to ride to 35th & King Drive, considering how long we had already been riding. To the gentleman in the yellow hoodie, I say to you thanks and I look forward to riding with you again.

I rode on. I was physically exhausted. Each and every rotation of the pedals took focus and effort. It was symbolic now. It was for myself and no one else. It was my own personal redemption that mattered. And, it only mattered to me.

I rode on. I struggled to get there. It was dark. Cars sped by.

I rode on. I had faith. I was going to make it to 35th & King Drive.

And, I did make it. One foot down, I sat on my bike in Bronzeville, on Chicago’s South Side. I was there. Alone, yet ecstatic. I made it. The journey was now complete.

Now what? I needed to memorialize this moment of triumph. My cell phone battery was dead and I did not have a camera. There was an easy enough solution. I rode over to a nearby Walgreens and purchased a disposable camera. I rode back over to the middle of 35th & King Drive and asked a couple of people to snap some photos of me. Then, I rode back to Walgreens and waited as the photos were developed. Next up, was a short ride back to my car, only a few minutes away at 23rd and State.


Reed at 35th and King – photo courtesy of Reed

The journey mattered. This journey started years ago. It was all a dream.

We are The Pioneers.

One or a thousand.

And we ride bicycles.

The more we ride,

The more we heal.

Published by

John Greenfield

John has lived in Chicago since 1989 and has worked a number of bicycle jobs, from messenger to mechanic to managing the Chicago Department of Transportation's bicycle parking program, arranging the installation of over 3,700 bike racks. He writes regularly for Time Out Chicago, Newcity, Momentum and Urban Velo magazines and works at Boulevard Bikes in Logan Square.

12 thoughts on ““One Pioneer, a Thousand Riders” by Oboi Reed”

  1. We at Bike In The Fast Lane Chicago realize how essential it is that the North Side vs. South Side (and rest of the city) issues be addressed as Chicago becomes ever more bike-friendly. Your decision to use the Critical Mass ride to engender your dream was an inspired one, allowing you to document quite literally how difficult it can be–from the mapping through the execution–to achieve a truly one-city/one-bike-friendliness reality. Your piece represents a poetic start to a ride that may be a little longer and rougher than it should be, but not at all impossible.

    1. Blogger & Biker – Wow, your words are amazing and inspiring! Thank you very much for the encouragement and the confirmation that dreams are meant to come true. Sometimes challenging. Always worth the effort. Look forward to a ride together soon… 

  2. When I started reading this, I knew Oboi wounld not give up and this story must have some sort of redemption. Oboi, you’re amazing & you inspire everyone to dream. xoxoxo

    1. Hey Mari – you represent that lovely balance of water and fire. that beautiful harmony of being both a student and a teacher. the uncommon nature of being a scientist and an artist. i saw it the moment we connected. i am deeply inspired by you. keep gettin live and keep rockin out. thank you for your kind words!


  3. as always my brother , your life exemplifies courage , determination , and the audacity to believe if you can , we all can !

    Love you much

    1. Dear brother Marshall – it is not at all surprising that you distilled the very essence of my existence into one short sentence – heal so that others may heal. thanks for the vision and clarity good sir. appreciate you immensely my friend and love you bruh!


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