Stories of Encounters With Chicago Homeless

After 17 years of church ministry, I am leaving Chicago. I have accumulated a Mount Everest of memories. Most of them bring a smile to my face and a tear to my eye at the same time. Others do not cause a visceral reaction nearly as much as they continue to mess with my mind about the intersection of 21st century America and the Bible. My encounters with Chicago homeless have shaken up my theology and leveled my simplistic view of the poor and how to respond to them.

Yet sometimes interacting with these marginalized people just leaves us with memorable stories that need to be told. Here are a few of mine.

September 2003, #76 Diversey Bus

I was reading my Bible on the way home from work at the back of the bus, typically a very quiet place. The Bible I was reading was one my church had given me with my name embroidered on the front. So it was special.

A man boarded and came to the back and did a typical plea to the riders for any change anyone could spare. I did not look up so I have no idea if he got any money. But soon after, he sat down in the seat next to me. He shamelessly peered over at what I was reading. He then commented about what I was reading being “garbage”. I asked what he meant. He grabbed the Bible and then very dramatically and quite loudly began reading from Revelation. And I do not mean Revelation 1-3, the section before it turns extremely odd to modern ears. It had blood and horses and riders and earthquakes, making his dramatic sarcasm quite effective. He asked me what the passage he just read meant.

I was far too stunned to respond coherently, and I honestly could not explain this passage from Revelation 6 succinctly. He scoffed. He then read another, from Revelation 8. People began to look at us. He again asked for an explanation. This time I said I had to get off soon and again did not have time. This was sort of true, as I had about five stops. But I was not ready to try to opine on Revelation for this man and the building crowd of onlookers.

He then began to pile on insults about Christians and how they do not know what they believe. As my stop drew nearer I began to long to get off the bus as quickly as I could. “Why couldn’t he ask me about Job? Or James?” I thought. But he knew what he was doing, I surmised.

I vowed to be more prepared…

As I readied to get off, I asked if I could have my Bible back. He said no. This incited a back and forth between numerous passengers all saying “Give him his Bible back” and “Answer his questions about the passage meaning first”. As my stop arrived, he reached out to give it back to me but I said with finality “No, I think you need it more than I do” and got off the bus.

I have no idea if he ever read it again. But I vowed to be more prepared to answer questions about the Bible next time, even Revelation.

2007 to 2010, Walgreens at Diversey and Laramie

I lived a half a block from this Walgreens and patronized it frequently. Every now and then a homeless man who was also mute would be outside with a little sign, asking for help. I watched many times as people would come out and give him a can of soup or a box of crackers or a bottle of water. And every time, he would joyfully react with expressive thanksgiving.

It impacted me because there is a stereotype that some people do not want food and merely want money to buy cigarettes or beer. And while I am sure that is true at times, it clearly wasn’t for this man. He deeply appreciated anything anyone could spare.

A few times he saw me outside my church, which was just a block from my apartment and on his way to the Walgreens. And so if we ever interacted at Walgreens he would point to the sky as if to acknowledge that I believed in God. He was a fascinating man.

I moved apartments in January 2011 and started going to a new Walgreens. I have not seen guy since, and miss seeing him and his kid-at-Christmas reactions to people being nice.

May 2011, Downtown

My best friend from USC and his newlywed wife were traveling back to South Carolina from Minnesota on their honeymoon and stopped in Chicago for the night. I had just performed their wedding a week prior, and we were excited to see each other again. They invited me for deep dish pizza. Since I had no car, I took public transit.

It was a gorgeous Spring day, so I got off the train well before my stop to walk the last mile or two. While I was about to cross a very busy crosswalk downtown with a mass of other people, a man who seemingly lived on the street impeded my progress and asked if he could ask me something.

I didn’t want to be late seeing my friends, so I very frustratingly told him to go ahead. He began to ask me a series of questions about why no one cares for homeless people and walk by them as though they were nobodies. I hemmed and hawed through a trite Jesus juke type answer, but that did not satisfy him in the least. He pressed me for a better answer. I said I really did not have time, as I was meeting my friends for dinner. He asked if he could have $20. I said I did not have cash, and it would take too long to go get it.

“Why am I not worth a few minutes of your time?”

He got irate at this point. He lambasted me for not practicing what I had just preached, about caring for the poor as souls made in the image of God. I said that this wasn’t true, but that it was not fair to keep my friends waiting. He said, “But I am right here. Standing in front of you. I am a human being. Why am I not worth a few minutes of your time? Why are your friends so important that you will cast me aside?”

I could have poked holes all over his argument. But I did something I know many of you will probably be disappointed in: I went to an ATM, and got $20 and gave it to the man.

I know some people have a hard and fast rule to never give cash to people, and I respect that. But while I adhere to that in general, sometimes I think the Holy Spirit can guide me differently. At that moment, I think it was good to give him the money. In a strange way, he earned it. He convinced me that I was not seeing people like him as image bearers. That lesson was worth at least $20.

Spring 2013, Moody Theological Seminary Campus

For one of my classes in my Urban Studies masters program, I did a group project with three other students on homelessness in Chicago. The parameters of the project were fairly broad, but we were asked to narrow it down to something very specific we learned.

One of the ladies in our group and her husband knew a homeless man well, so we decided to talk to him and get some ideas. My classmate and her husband were very noble in how they treated and interacted with the man, whom I will call “Harry”. They visited with Harry once a week at minimum and helped him with food and like things but also with work. It was extremely impressive to me how they balanced compassion with mobilization. And as we talked to Harry we realized that he did not want a lot of charity. He did not want to go to soup kitchens and rescue missions. He actually accomplished a lot in providing for himself by collecting cans.

I had boxes about homelessness

The more we talked to him the more complex we realized his situation was. And not just that he was homeless but about what it meant for people like us to help him. We realized that what my classmate and her husband were doing was something we believed Jesus taught in Luke 14 about not just serving the marginalized, but associating with them. Spending time with them. Treating them like people and not projects. My classmate and her husband knew how to help Harry best because they knew him and did not try to fit his predicament into a box.

I had boxes about homelessness before that class. And Harry shattered them. Out of this experience was born a sermon I preached for my church which I turned into an article for REO called Social Justice Beyond Social Media. The issue of association by reaching across instead of merely serving by reaching down revolutionized ministry in general for me.

There are many others, and some of them do not have very happy endings. I am positive that I have reacted poorly at times. I am positive that I have been hoodwinked at times. And I am positive there are no easy answers to dealing with homelessness at times when it is in your face and not on a TV screen or in a statistic on a page.

Yet I am very thankful for what Chicago has taught me about people. Especially people most others do not want to get close to, much less interact with. Often my interactions have been (to paraphrase Shakespeare) thrust upon me. But that is how God works. Often grace finds us when we are not looking. It gets in our way. And praise be to God for using whatever he can to teach him about how to love Him and how to love others.

Gowdy Cannon

I am currently the pastor of Bear Point FWB Church in Sesser, IL. I previously served for 17 years as the associate bilingual pastor at Northwest Community Church in Chicago. My wife, Kayla, and I have been married nearly seven years and have a 3-year-old son, Liam Erasmus. I have been a student at Welch College in Nashville and at Moody Theological Seminary in Chicago. I love The USC (the real one in SC, not the other one in CA), Seinfeld, John 3:30, Chic-Fil-A, Dumb and Dumber, the book of Job, preaching and teaching, and arguing about sports.

3 thoughts on “Stories of Encounters With Chicago Homeless

  • June 29, 2019 at 9:38 pm

    Kirby is involved in a ministry along with a network of other churches in our area called “ChristNet”. Each church adapts itself into a homeless shelter for an appointed week and hosts around 30 guests that are in the program. The first year I was able to be a part of it, our small group prepared dinner one night and we simply served it and sat down for a meal with the guests. It struck me that their stories were so “normal” right up to a point where some sort of luck turned bad or they maybe made a couple bad decisions that had unimaginable consequences. I realized I had just never given much thought to the reality of how possible homelessness could be for anyone, given a few turns in life’s road. There was one year where one of the guests had actually graduated high school with my brother. One of his parents passed away unexpectedly and the other moved away to escape the gravity of the situation, his job folded and before he knew it he’d been evicted with nowhere to go. The program guides the guests with job opportunities and living assistance beyond their eligibility with ChristNet, many are helped back on their feet. I was working on a house in a neighborhood quite a distance from our church awhile back when I recognized a former guest riding his bicycle down the street. He stopped a few houses down and used his keys to open the door, I couldn’t help but think he’d returned to having a place of his own and I got to see a glimpse of the success of the ministry. I think most people who’ve had the opportunity to serve during our week would tell you that the experience and interaction benefited them as much or more than the folks that we were trying to help.

    • July 3, 2019 at 9:08 pm

      That is great. It so coincides with what I was trying to say above. There are absolutely people who want to take advantage of the system or don’t want to work or whatever. But many people I’ve met were much more complex.

  • June 30, 2019 at 9:35 am

    Gowdy, this is so powerful and convicting. I always appreciate how candid you are about your struggles, but you don’t wallow in them. Instead, you use them to grow and mature in Christ.

    I have become jaded to people like you describe in this article. I need to remember, as you said, that they are image bearers.

    Thanks for this reminder and challenge.


Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.