Author's Note: This post was pulled from Robert’s 2005-08 personal journal and reworked.
Introduction
The book, The Big Sort: Why the Clustering of Like-Minded Americans is Tearing Us Apart came out as I struggled to look for work during the Great Recession in 2008. It’s due for an update given how technology has exacerbated all the book’s conclusions with the merging of what I call the ‘tech triad’ of high speed internet, smart phone and social media. In addition, various types of jobs, especially freelance consulting and other remote work has allowed us to self-sort faster than ever before. That process is what keeps us from learning from others despite being more connect to each other than ever before. Lived experience does not happen on the internet.
Most of my life has been an investigation, a desire to understand ‘why things are the way that they are’, particularly in my rust belt community on the fringe of Gary, Indiana. Dad raised me to live outside my comfort zone because there are more teaching moments that way. Some of his approach is covered by stories in The Hard Way on Purpose: Essays and Dispatches from the Rust Belt. I’ve taken that advice to an extreme (such as biking 825 miles over 10 days with no training) and built that into my normal. Being in a room full of people that don’t look, sound, believe or act like me is fun. I regularly argue politics and religion with many of my acquaintances but of all the unique people I’ve met in life, Robert the Drug Dealer probably had the most impact on my thinking about socioeconomics. His lived experience trumps every PhD writing on the subject.

A Vacation
My close friends from college were destined for bigger things and all of them went straight into graduate or law school while I flailed around looking for a job. A few contacted me about getting together during their fall break. I hadn’t had a vacation in as long as I could remember so I told my boss, Mr. Hooks, that I’d be taking a few days off. Between working as a contractor for the steel mills and sending resumes to Chicago all night long, I was worn out. This trip would be an excellent opportunity to recharge and figure out my next move, especially after seeing the stock market’s record drop for the year that September.
The plan was for us to visit one friend at the University of Illinois for an extended weekend. I had just moved to Lincoln Park, Chicago a few months earlier and left my two cars in a parking lot at a friend’s apartment complex back in Indiana. I told a former roommate that I would take Chicago’s CTA train down to the Hazel Crest train stop, the perfect spot to connect on his route.
I didn’t know much about Hazel Crest other than the receptionist from my internship at Merrill Lynch (in Merrillville, Spring 2007) lived there. She was the only Black employee but seemed middle class. According to sources on the internet, the city had crime but it was dwarfed by neighboring communities such as Harvey. Five years later, the website HeyJackass: Illustrating Chicago’s Values, would emerge to sarcastically cover the shootings. I wasn’t scared to land there but the X factor would be if my old roommate arrived on time. He was late for every event we ever did together other than a college basketball game. He always seemed to be 20 minutes early or more, wondering why the rest of our friend group wasn’t there yet. I had a feeling this would be a repeat but maintained my optimism.
Stranger Danger?
With my luggage in tow, I was the only person to get off the train station and it seemed pretty quiet out. A man was laid back on the bench, and he didn’t move much. He was dressed in streetwear, too nice to be homeless. About 10 minutes passed, a few more trains went through, and nobody got on or off. After making eye contact a few times, I got nervous and decided to break the ice with him. “You got one of those for me?” I said, pointing to the 40 sitting by his foot. “You wanna drink?” As he picked up the bottle, he waved it in my direction. “Nah, I was just kidding. I’m more of a whiskey guy myself.” It wasn’t a true statement then, but I had no interest in sharing a bottle with such a stranger.
He wanted to know what I was doing there, and he made sure I understood that I was the first white person he ever saw on the South Side. I didn’t exactly want to tell him that I was headed to a farm to eat steaks and shoot shotguns, so I just told him that I was waiting for a friend that would arrive anytime now and this train stop was the most convenient spot for us to meet. I didn’t want him to think I would be alone for long.
The man then proceeded to ask me if I wanted to buy a brick. “What’s that?” I said. “You know, a brick?” “No, I don’t…” I responded.” Then he started to get uneasy and stepped back. “Are you a cop? Do you have a wire?!?” I nervously laughed out loud, thinking things could go downhill fast, so I blurted out. “Do I look like a cop to you?!?” Pointing at the large logo on my green hoodie, “I don’t think an undercover cop would come to the South Side of Chicago in Abercrombie & Fitch.” Then I pulled up my sweatshirt, showing him I didn’t have a wire on.
That seemed to satisfied him. The man then pointed to a car about a block away as we looked down from the platform. “That’s where the brick is, in the trunk.” Once I returned to my senses, I understood what he was talking about: a brick of weed. “To be honest, I don’t smoke,” I said. The man crunched up his face and looked at me like I was crazy. “Don’t smoke?!? Broooo, everyone smokes!” “Yeah, I just prefer alcohol as my vice.” To which he laughed.
I inquired about how he got into the drug trade. The man dropped out of high school and joined the Black Souls gang, of which I was unfamiliar. I only knew about the Latin Kings and Gangster Disciple (GD) Folks as they started to move to the edge of my community from Gary in the mid 90s. A few friends were “beat in” when I was in 6th grade but I don’t think they were ever fully immersed in the culture much less the other activities associated with gang life. I distinctively remember giving a science project presentation and the teacher said “Be sure to tell all your folks…” and my buddy busted out laughing, causing a class disruption. When the teacher inquired about what was so funny, he couldn’t explain it to her…
Anyways, this man had a few small jobs as an unskilled laborer but was always let go when his employer couldn’t pay him, and the drug trade was WAY more lucrative. When I told him that I was also having trouble finding work despite having a college degree, he was quick to blame President Bush for the poor economy. I had no interest in getting into a political debate but merely asked him, “Do you really think one man can single-handedly control the economy?”
It was then the man started to blame white people at large for all the things that were happening around him but he couldn’t explain exactly what that meant or how. It was just “what his gang had taught him” and there was no believing anything different. “You might be the white devil and you don’t even know it,” he said, pointing and calling out the unique color of my eyes. Our faces were near nose to nose. Again, I got nervous as hell trying to think of what to say next. “You know what? I really don’t like you selling drugs out here. You could get killed,” I said.
Who hasn’t been shot?
“Nah bro, I’ve already been shot a few times. If God wanted to take me, he’d already done it.”, then voluntarily lifted up his own hoodie, showing me scars of both the entry and exit wounds. I pretended to not see the gun that was in his pants. It was surreal. I didn’t know a single person who’d ever been shot, and this guy treated it like it was business as usual.
I started to get choked up because this really bothered me. How do we live in the richest country in the world, yet some people believe this is their only option? They aren’t trying to succeed but to merely survive? I’ve never had white guilt because my family has spent 400 years in this country without intergenerational wealth but the injustice here was something I couldn’t internalize. Being from Northwest Indiana, you know more about Chicago because of the media market. With a shooting reported on the news every day, even the uninitiated get numb and desensitized to the repetition.
A Venture off the Beaten Path
I’d rarely given strangers on the street cash (I make them eat with me), but something came over me, and I just wanted this guy to take one day off from the hustle. “Is there an ATM around here?” “Yeah, why?” He pointed to a gas station a few blocks away. “If I give you $40, will you take the rest of the day off and not sell any more drugs?” he laughed. “Well, it’s been pretty slow today, so yeah.” Next thing you know, I’m venturing off into the hood, walking into a rough-looking gas station to pull out cash.
We walked outside and I have him the cash. I didn’t have any advice for him and only shared what my parents taught me: maximize education at all costs, be honest and work hard. With that, I told him to do what was needed to get his GED, as it would open more doors than he thought. He nodded in agreement.
As we got ready to leave, I shook his hand and said, “Hey, I never got your name.” He replied “Robert" to which I responded, “No way, me too!” The guy didn’t believe me, so I had to pull out my driver's license to prove it.
“Maaan, you ain’t bad for a white boy!” and he gave me a ‘man hug’ as his entire demeanor completed changed. The accented “bros” he used to finish most sentences with and the tense interaction we had completely melted away. We were two guys living parallel lives but instantaneously changed forever by this one interaction. After leaving the gas station, we parted ways with a hand shake as he headed to his car and me back to the station.
Robert vindicated gang temperament and interactions I read about months earlier in Gang Leader for a Day: A Rogue Sociologist Takes to the Streets, a (then new) book I came across after its author was mentioned in Freakonomics: A Rogue Economist Explores the Hidden Side of Everything.
Within five minutes, my buddy arrived.. an hour late. When I jumped in the car, I was annoyed from his usual tardiness but quickly realized that if it weren’t for that, I wouldn’t have this story. My dad’s timeless wisdom peered through again: don’t assume anything about anyone and you can always learn something from everyone. I grew up on the first rung of the socioeconomic ladder but meeting Robert taught me that some don’t even have one to climb…