Terry, My Homeless Friend in Wicker Park

Terry’s regular spot immediately outside of the Division Blue Line Stop near Ashland & Milwaukee

Terry is a drunk. He’s been a drunk his whole life. When he was 10yrs old, his Catholic school priest did the things we hear about Catholic priests doing. Now at 60yrs old this Irish-bred, Mt Greenwood man calls the streets of Wicker Park his home.

Most nights he can be found outside the Division Blue Line stop near the CVS. Even having spoken with him on several occasions over my last 2 years living in the area, it still takes him some time to remember me. Which, I think it’s because he doesn’t see faces most of the time. Just the bottom of people passing by.

The First Time I Met Him

It was about a year and a half ago when I first met Terry. I didn’t know his name at the time. I had passed him on my way to the grocery store and grabbed him a sandwich to deliver on my walk back. Upon giving him the sandwich he told me he couldn’t eat it because there was cheese on it. I told him he could just pull it off, but he insisted he’d still get sick from it.

I was a little jaded after that. Had the thought of, “I’m trying to help, but fine, fuck you then!”


I told the story to a friend of mine who then began referring to him as “Cheesy”. It became an on-going nickname, and then…I started to see him more. Not because he was around more, I think I just started to notice him.

So, I started to talk to him. Like an old friend you’d see at the bar all the time; a real life, Frank Gallagher. Only instead of sitting at some bar, we’re literally sitting on the street, which happened to be where he also slept.

Terry asleep at his usual spot.

I decided to strike up a deal with Terry one day. I told him I would pay him $1, every time I passed by, if he said “hi, Joe” and gave me a good reason to be alive.

Why It’s Good to Be Alive, According to Terry

1) He had the chance to watch construction workers build a new part of an apartment complex. AND they bought him lunch.

2) Very excitedly, because he had a 6 pack.

3) Because he found out some news from the doctor. “They thought I had something bad, but it turns out I don’t” he said. Followed by a big thumbs up.

4) A drunken Terry told me to “get fucked”. Gotta respect him for it.

5) Because the bars were open.

I tried to buy another lesson one day but he wasn’t up for it. He looked up at me with a rawness in his eyes.

They were red.
Tear filled.
He was still mid-cry when he told me he had just found out his father had died. Yesterday.

Terry commended his father for making it to 91, and being able to die of old age. I didn’t know what to say. So I went into the CVS, grabbed us a couple beers, and hung out at “our bar” talking with him.

Since then, I’ve been a little more distant. Sometimes walking past him without saying anything just to see if he’ll notice me. He doesn’t. Mostly because he doesn’t look up very often.


Time has always been a thing with me, I’m always in a rush. I finally found some time to sit with Terry again recently. I decided to restart my lessons by prepaying him for 12 new reasons it’s good to be alive.

The first new reason he gave me: honesty.

Terry and I outside of Tocco Restaurant on Milwaukee Ave, Wicker Park

I’m excited to see what other reasons Terry has in store for me over the next few weeks. Every reason he’s given me is from a life I can’t even begin to understand. If there is one thing he has taught me, it’s that the little things matter. The little things add up.

We Need to Build Real, Physical Communities Again

The Latest Report from the Chicago Transit Authority, in May 2017, reported over 6,300 people have passed through the Division St Blue Line station that month. Meaning thousands of people pass this man every month, turning a blind eye.

If we want to look for change, we can look for it on our own communities.

Instead, we take to digital communities. We’ve let social media create a world that seems too big to change, but gives the illusion of accessing the most powerful man in our nation…through a social network.

We feel like we’re affecting change by rallying online and voicing our opinions in an echo-filled digital platform that takes your ideas. It takes them and sends them down a proverbial toilet because a chronological sort is more important.

Because social media tells us that was is new is more important than what is right.

I have a hard time thinking the world is too big to change.
“The world” is what I can touch.
What I can do.
What I can affect.

Maybe instead of looking to change the nation by posting on social media, we focus on changing the lives of the people around us. If we start to pull ourselves out of this digital world, we can get back to creating the change we desperately need in the real world.

It starts with politicians leading by example. So Senators, Congressmen, et. al, if you want to send your condolences to the families of the Las Vegas tragedy — send them!

But do it in real life.
Not sending your condolences through a tweet.

Life isn’t lived online in a digital world. Terry doesn’t have Facebook. But he is a person. He lives in my community. And I’m no one special, but if I can do just a little bit, to help someone feel a little less alone in this world, maybe I’ll be able to leave this place a little better than when I came into it.


This article was published with approval from Terry. If you happen to be in the area, feel free to say “hi” to him, he’ll appreciate it.

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