Leadership Lessons From a Teenage Gang Member

Updated: Feb 18, 2019


When I saw the large knife clipped inside his waistband, my first feeling wasn’t fear. It was disappointment.


I was walking up the stairwell to the main office like I did every morning. “How are you doing today, Carlos?” I asked with a smile.


“Doing great today Mr. John,” he said back with a sleepy grin. “Kinda tired though... I worked late last night,” he said, stretching his arms above his head.


That’s when I saw it; an oversized folding knife. Though fairly well-concealed, the shiny metal clip was a dead giveaway and caught my eye immediately.


When working with tough kids, it’s sometimes useful to not let them see what you notice at first. When there’s a never-ending list of things that are not ok, don’t seem right, or otherwise raise suspicion, you have to pick and choose your battles. This often gave me time think and strategize.

Carlos didn’t notice that I’d seen the knife. He went off to class. I walked on and around a corner, then paused. Crap. What to do now?


At the time, this was one of the more dangerous high schools in New York City. Though relatively small, serving only a hundred or so students, the school population was made up entirely of young people attempting to transition from long-term detention; juvie lock-up on Rikers Island and other secure locations from around the various boroughs.


These weren’t petty vandals and shoplifters. Most were affiliated with major gangs and/or the drug trade. Many had serious incidents of violence on their rap sheet; age being the only thing that had kept them from doing more serious time. A lot of them hadn’t been to a “normal” school in many years. Many of them had basically grown up in the city’s various detention facilities from a very young age.


The idea behind this particular school was to give these long-term detainees a transitional step back to their home schools. This school had a very high staff-to-student ratio, ample counseling, better credit recovery options, and a more consistent level of security than your typical large urban high school.


The students sent here would also, hypothetically, have a bit of insulation from their old relationships and conflicts back in their home neighborhoods. Not a bad idea on paper. In practice, things were a bit more complicated.

One thing the school planners hadn’t fully considered was that when you brought students from diverse boroughs and neighborhoods together in one central location you were throwing representatives and leaders from many rival gangs all together in the same place.


Some of these students’ gangs were not on friendly terms with one another on the street. Others not in direct conflict, saw this new arrangement as an interesting new networking opportunity.


This was the school’s second year of operation. After many months of chaos, the first year had ended in an evacuation after students set fires in multiple parts of the building. All of the staff quit. Literally.

The one exception was an experienced, street-smart, caring, and tough-as-nails ex-lawyer turned school administrator. She decided to have another go at this experiment and rebuild the school from the ground up. Most of the same students were returning. The entire staff had been replaced.


Gang life does provide money, respect, and the other trappings of any criminal lifestyle. However, the most immediate benefit of being in a gang is a family to belong to, however destructive and violent it might be, as well as protection. However, the tenuous ring of protection that a gang offers has limited boundaries; usually only a few blocks in practice.


Asking all of these young people to come to an unfamiliar part of the city every day meant that they had to cross through multiple sections of “enemy” territory just to get to school.

This brings us back to Carlos.


I had been contracted by the school to help the staff and leadership build a safer and less chaotic school climate than the previous year. I was not a staff member; just a professional coach. The previous year wasn’t disastrous only because the school was full of tough kids, but also due to a lack of consistent vision and expectations from leadership and the consequent disjointed lack of cohesion among staff.


This year was different. Together, we started the year by having some hard conversations with administrators and staff, ensuring that everyone had the same expectations of students and each other. We also spent considerable time with students during the first weeks setting clear and firm bottom lines, while also letting them set goals and expectations with one another.


One clear commitment the students made to each other was to leave all gang activity at the door. The reality was, once students trusted each other enough to be honest, most of them were looking for a realistic off-ramp from gang life. Graduating from high school would be a good start. With that goal in sight for most, they set some clear rules for each other. Some of the most important norms they set were no gang colors, no drugs, and especially, no weapons in school.

They had jointly agreed to make the school a sort of “demilitarized zone” where they could set the usual stressors and dangers of street-life aside. This wasn’t something the staff could have imposed by their own will alone. Making these commitments real required a lot of painstaking and intensive work to help the students hash out these agreements directly with one another.

When Carlos brought the knife into school he’d not only broken the law, he broke that agreement with his peers. The secondary risk was that, once others found out, they would feel the need to re-arm as well.


For a few moments, I honestly considered saying nothing about the knife. Frankly, I’d come to depend on Carlos. He was a leader among the student body and was instrumental in helping to deescalate things early in the year. I had turned to him many times for help with tough situations among the students.


Part of me wanted to protect him. Another part of me just frankly didn’t want to deal with it since things were going so well. If I’m being honest, I was also a little concerned for my own safety. Being known as the outsider who “ratted-out” a respected student was not an appealing thought.

In the end, I chose to tell the leadership what I’d seen. They could make thei