There’s No Such Thing as a Bad Boy

Stephen P. Conrad
Real
Published in
14 min readAug 25, 2023

Can a boy be born bad?

Credit: Juvenile In Justice/Richard Ross

“There is no such thing as a bad boy” — Father Edward Flanagan.

That’s the slogan carved into a wooden plaque that hung on the wall in the CPS public school office of the Cook County Jail school unit.

The principal of the school wing Joe W. or as he was affectionately called, Polack Joe, by those of us living in the school unit, very much believed in that slogan. Father Flanagan was his boyhood hero. I’m not sure any of us had boyhood heroes.

Much of what I learned in life that I did not want to emulate, I learned from watching and listening to my old man. That’s just real. I suppose it’s not a pretty picture, but it’s a realistic one.

One of my few fond memories is of my little brother and I burying ourselves beneath the bed covers as we watched the old 1938 black and white movie ‘Boy’s Town’ with actors Mickey Rooney as the protagonist ‘Whitey Marsh’ and Spencer Tracy as ‘Father Flanagan’.

I remember painfully wishing that I was Whitey Marsh and that someone could come to our rescue. No one would be coming.

‘Boy’s Town’ was about the battle between good and evil for the hearts and souls of a young boys on the streets of New York City. Could the tough, good-hearted father wrestle the hearts and souls of these young street urchins away from the streets and criminals that sucked them in? Or would they be destined to a life of jails and institutions.

Just as it did back then, today the correlation between Joe and ‘Boys Town’ is firmly imbedded in my psyche. One of the most straightforward and positive characters of my youth was one who entered my life as I sat in one of darkest, most dangerous places in America at the lowest point of my youth.

Like Father Flanagan founder of the original Boys Town in Omaha, Nebraska Polack Joe never gave up on us, even when we gave up on ourselves. There were others, but Joe most affected my life and psyche from those years.

Even during the most trying times of my youth I managed to garner what positive I could from negative situations. My mother taught us this. I watched her do the most she was capable of with the few resources available to her. But it was her words of positive affirmation that stayed with me and would most affect my life. Her words would help me survive and keep me alive.

I had that much. A lot of the boys did not have even this.

But as the good Father Flanagan and Polack Joe always said; “There’s no such thing as a bad boy.”

Maybe what the good father meant was that they wouldn’t be so bad after he had a chance to work on them. But I can tell you firsthand there were a lot of bad boys there. I was no exception. Many of the kiddie-cons serving time in Cook County Jail had worked overtime to prove that slogan wrong.

While I should have been out chasing girls and getting ready to graduate high school, I spent most of my 17th year of life in Cook County Jails school unit. I spent my time doing what everybody else did, playing cards, fighting, bragging about shit that never happened in our lackluster criminal careers, girls we never dated, and the loves we never really had. Oh yeah and crying ourselves to sleep at night as we lay in our cold grey cells.

Love? Ha! I mean, what the fuck could we possibly know about love, we didn’t even know what the word meant. Other than the obligatory parental lip service or a twisted version of it, many had never given nor received anything remotely close to it.

We were all just trying to get by until the next court date, or the bus ride to the joint.

Even the toughest boys had something to cry about even if it was only crying to themselves alone at night. Everybody was a tough guy until they had a 50-year bid staring them in the face. It was a lesson I learned and one I learned quick. It was also a lesson that would remain with me throughout my life. The only truly tough guys I know are dead.

At times we may have horse played and joked as kids do, which was often, other times, things became deadly serious. Everyone had an agenda. This was no prep school.

Maybe Polack Joe was right, maybe there is no such thing as a bad boy, only misguided youths and those who lacked structure in their life or someone who cared and an absence of a positive environment.

At home it was just ma for us, it was no one’s fault. I left early around 14 years old to live with friends or wherever I could find to sleep. I would come home a few times a week to check in so she would know I was okay. Make no mistake, I knew my mother cared but between working to feed us, keep the lights on and her struggles with mental illness she had little time to share with us as we grew up. I grew to know her personal demons as well as she did.

As for my old man, sure I love him he’s my old man. Yet a sad reality is he cared about himself first and whatever time and experience he did have to share he did on his own terms. The booze and the pills came first in his life. He wasn’t the dad who took the time to teach you about the “birds and the bees”.

He was an alcoholic and pill popper who did what alkies and addicts do best, take care of themselves first. It was ma that did whatever she could with whatever she had to work with which was not a lot. But she tried more than anyone I ever knew. She was strong and taught us to be strong. That would prove the most invaluable lesson I ever learned. She made me a survivor.

Most of the boys in the county jail faced similar struggles and lacked any positive role models in their lives.

Like so many kids, at that age I was unwilling to share my struggles and sense of hopelessness with anyone else. I viewed what others had failed to do for me in my young life as my fault. I accepted responsibility and fault for things that were never on me. I refused to blame others for lack of guidance and direction. I mean how was it their job to teach me?

It would be decades before I would finally admit that, yeah, maybe some people did fuck up by not doing what they could have done to guide me in the right direction. Maybe I would have stood a better chance in life in a lot of ways. Maybe not, but I would have stood some kind of chance.

At this point it’s all water under the bridge. Back then, however, I was a kid who thought he was a man — who had never even been a kid — who thought he knew it all, who believed he had all the answers. I didn’t know shit. I would find that out soon enough.

People like Polack Joe, Jack Walls and Mother York were my teachers, and the Cook County Jail gang and school unit was my classroom.

I was a week in on the unit when one of the folks, a kid I knew as Lil’ Gram approached me in the dayroom and asked if I could read and write. The dayroom, just outside your cell door was the place on the tier we played cards, watched television, exercised and conducted business.

Lil’ Gram was folks. I was folks as well. So that meant that Lil’ Gram and I were bound together, our duty was to look out for each other and any other folks on the deck. Back in the 1980’s there were street gangs everywhere and every one of those street gangs for purely purposes of profit, protection or self-preservation were allied with other gangs.

When the gangs organized there were those gangs that wanted nothing to do with it. Those who did sign on to organize fell under an umbrella recognized as the “folks” alliance. Those who wanted nothing to do with it ultimately ended up forming the “people” alliance. They people were our opposition on the street in county jail and in prison.

We adopted unique symbols used to identify us as soldiers belonging to whoever we were with. Our own gang remained autonomous but existed under a larger organization with a greater purpose. At least that was what we were told to believe. That was the idea. Shit, fell apart within alliances as often or more than it stayed together.

If the top dog was killed the new dog may not be as inclined to be as family friendly. If an administration crumbled and a new one took over, they may not have their shit together and wars would break out sometimes within a gang. Get it? Criminals are criminals, greed usually wins.

Not to be outdone by others we also had rules, laws, and regulations. These were called our ‘religion’ or ‘literature’. This was basically just your gang or nation family history and the laws dictated what you could do and what you could not. Not unlike a league of nations that forms to ward off any aggression from opposition nations.

If you violated a law of your own gang or one of the larger nation you could end up catching a violation, a beating. Or you could be killed. It wasn’t at all uncommon to hear someone got knocked down or killed. No one liked it, it was just a reality you had to accept.

But the laws were not applied evenly or fairly for everyone. I mean come on; we were criminals and criminals don’t like to share. If they see a way to keep most of the money for themselves and eliminate potential competition, then they take advantage of it. They take a shot.

In the end it was all about greed, power and stupidity. The latter applying to most guys. You don’t get into a gang or organized criminal endeavor because you’re normal or have positive things going on in your life. On any given day anything could happen. Most of us were not known for our impulse control.

The short of it is, in Chicago, the smart gangs got together and decided it would be better to unite and work together. Well, better than daily battles over profits and territory that could easily be shared to turn a better profit.

Now let’s be honest that didn’t mean everyone received an equitable share, no way, no how. The guys on top scraped off all the cream while the foot soldiers took their marching orders and put the work in. The big dogs took care of their own while the rest of the suckers languished. Sound familiar? Capitalism? Yeah, it sounded much like that to us too. Like I said, by design.

We were street kids, not dummies. Maybe we weren’t as formally educated as some rich kid who had all the advantages, but believe me, we knew what we were doing and knew how to make a buck. The idea, just like capitalism, was to earn and bang your way to the top.

For most, all those high ideals and lofty goals got lost somewhere. The truth is most all of it was bullshit. It always had been. It became about self-preservation, survival.

It was the same old pyramid scheme that existed forever, if you’re seated at the table you get to eat, if not you get fight for scraps. Anywhere else on the food chain, you’re fucked.

In the county jail everybody associates or is hooked up with someone. It’s the only way you survive. I mean there is a whole lot more and much more involved to it than I am giving you here, but you get the general idea of who, how and why.

When I went into the county jail, I was in a gang that fell under the folk’s alliance. So, I had some insurance, not much, but enough to get by. Some kids had nothing.

A lot of the boys on the school wing were not the brightest, best educated or literate, so when Lil’ Gram approached me and asked whether I could read and write he had good reason to ask. It just so happened that I could, and he wanted to fill a seat with an ally. That ally was the jail administration. The in jail public school system.

I didn’t have a whole lot going for me, but I was no dummy. I came from a long line of highly intelligent people even if many of them were themselves misguided or criminally inclined, they were no dummies.

I had heard continually over the years about how intelligent many of my uncles were by some of the most high-end, notorious criminals of their time. It seems they could have been anything they wanted to they just didn’t want to be anything else. By way of their own tours through the prison system a few of them managed to become college educated. But they decided to invest their lives in crime.

Not exactly an intelligent move, right? Maybe not, but if you’re also impulse challenged product of the streets, you go for what’s right in front of you. So, I had good genes. I also had a natural inclination of how to navigate treacherous waters and operate on the streets and in jail. Good instinct and intuition served me well.

There was one thing I loved in my life and had loved ever since I could form a thought, the art or the written word. The telling of a story, beauty of a book and the words that hid between the covers. Those words took me to places I had never been and taught me about worlds outside my own I could one day go if I chose to.

These are the few things that would ultimately, albeit years down the line, save me and guide me to a new life. But back in those days, all I sought out was something or someone that would save me from myself.

I quickly accepted the offer of a job in the school wing office ‘Lil Gram has offered me. Polack Joe was looking for a guy to replace one he had recently lost to a long prison sentence. Mousie. He had taken the bus ride to the joint, where most of us would ultimately end up.

Mousie was a kid who by the age of 14 had earned a long rap sheet. He would become a shot caller for one of the major street gangs in the city. He and I were allies on the street. He had just been convicted and sentenced to a long bid.

Once you were sentenced and if that sentence was 10 years or more you were moved immediately for security reasons to Division One and wait until you would be ‘banked out’ or shipped out to Joliet State Prison to process into the system. Eventually you shipped out to the institution you would do your time in for the years to come.

Mousie, who was well-known on the street and in the county, would end up serving the better part of twenty-eight years in prison on a twelve-year stretch because he had to do what he had to do to survive.

It would be almost three decades before I would ever see him again. As for me, to be asked to fill his seat was a big deal and not something just anyone got offered. You had to be trusted. I was now in charge of the information flow within the county jail. There were benefits that came with that kind of position.

In the CPS school office, we were all misfits amongst misfits. The clerical jobs we had were often viewed with jealousy by other inmates who didn’t get to realize the privileges and perks that came along with the job.

Jack Walls the assistant principal in the office was a tall well-built older gentlemanly black man. Jack was the extreme opposite of Polack Joe’s tough-talking 50’s greaser type neighborhood guy persona. He would often remind us that we were, himself included, all misfits.

Jack was a religious guy who would say that Jesus hung out with misfits and wasn’t with the in crowd. Jesus, Jack said wasn’t part of the system and dedicated his life to rallying against the system. He hung out with hookers, thieves and murderers committing some of the most criminal and controversial acts of his day. The difference was, He did it to better the lots of others, not his own. He took care of others, not took from.

Jack had a way of imparting upon us his religious scriptures and theological wisdoms in hopes we would try to lead better lives on the inside and ultimately once we, if we, got back out into the free world society. That was a big if for a lot of us. We always respectfully and intently listened, we then discarded anything he taught us, or did we?

There were six boys working as clerks at any given time in the CPS office. During my time there the seats were filled by Flaco, Lil’ Gram, Fish, Rerun, Fonzie and myself, Bambino. It was a casual mixture of race, ethnicities and various gang affiliations.

During our time in the office, we weren’t allowed to represent any affiliation with a gang. If we were to be able to do our jobs as clerks in the office, we needed to leave our gang life at the door. That included representing to any of the fish, what we called the new inmates we processed into the school wing.

That was essentially our job. Processing all incoming inmates into the Cook County Jail system and the CPS school unit. We were free county labor with a few fringe benefits. We had access to all their files, case information, prior criminal records, and affiliations. We couldn’t share information out in the open, but we were essentially the gang information clearing house and any necessary information considered the intelligence arm of our respective gangs.

That was the deal. We would go to school and study for our General Equivalency Degree or (GED), except none of us ever attended an actual class, while we performed office duties and clerical work. For boys barely out of our teens, we had a long reach, already privy to information that only guards, and civilian county staff were.

In the office, we earned a mutual respect for one and other as every one of us were already multiple felons and each one of us were facing sentences ranging from at least four to fifteen years on upwards to natural life in prison. Every one of us was just waiting for the best deal or plea bargain we could get on our case and a free bus ticket to the joint.

Nobody really wanted to go to the penitentiary, but more importantly no one wanted to stay in the county jail. Prison was the better deal we learned from the kids who had already been there and back.

We were no dummies. Kiddie-cons with brains is what we were, even if we didn’t use our intelligence for positive means. We also knew that intel was a valuable commodity, the ability to provide it gave you some rank, privilege and a degree of protection. Again, not much, but something more than others had.

The days would become nights and the nights weeks and months and even years. Time passed slowly until you didn’t realize it was even passing you by at all.

In the end, looking back on this period in my life I had many hard learned lessons. I realize all the lessons learned during this time and during all the years that I would be incarcerated, it all boils down to one thing; no one can make you better, it’s all on you. No one can take anything from me, whatever I lost I gave away. Desire to change comes only from within. Rehabilitation is an inside job.

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Stephen P. Conrad
Real
Writer for

A nomad, a gypsy at heart, writer, actor, artist, anti-sycophant, socially maladjusted and comfortably near complete insanity.