Overcoming the Heartbreaking Case of Bobby

I’ve been reading lately about the school-to-prison pipeline [2] and reflecting on my work as an administrator. I think frequently about the toughest day of my career in education: the day I had one of our students arrested [3].

Bobby was a freshman on my caseload and a frequent flier in my office. Young enough to still be described as cute, he had a baby face, wide brown eyes and shaggy dark hair. His previous school had expelled him, and he assured me that he had learned his lesson and was ready to make a positive change. I believed him.

As the school year progressed, Bobby was in my office for a variety of reasons: suspicions of smoking marijuana, tagging lockers and skipping class. At his mother’s request, he was referred to a community counseling center for drug use. Each time I saw him, he told me what I wanted to hear, and we both went on with our lives.

That spring I communicated with his counselor on a regular basis. She told me he was no longer agreeing to weekly drug tests and that his mother was at wit’s end. The police had picked up Bobby and his brother for tagging, and Bobby would often stay out all night. His counselor was about to drop him from her caseload due to noncompliance with her program. She had too many other kids on the waiting list who needed help and she couldn’t continue with a kid who didn’t want it. 

Bobby was sent to truancy court. His counselor had a bed reserved for him in a drug-treatment facility and she hoped the judge would order him to it. We collectively held our breath that day in hopes Bobby would get the help he needed. He was not sentenced to treatment. He was dropped from counseling.

The next day, he was in my office for stealing a stack of T-shirts from the student store. “I just don’t want to be here,” he said, but refused to tell me more. I wish I had pushed him. I really wanted to hear what he needed.

Tagging in the neighborhood and on campus increased. Concerned for him, one of his friends told me Bobby was responsible. Our school custodian had witnessed Bobby tagging a locker, tags that matched those in the neighborhood. A colleague and I searched Bobby’s locker and found similar tags inside. We called him down. He wouldn’t talk to us.

We brought in our school resource officer (SRO) to talk to Bobby.  He asked if we wanted to have Bobby arrested for destruction of property. I called his mom. “Yes, please,” she said. “I don’t know how else to help him.” As a mother, this breaks my heart.

I stood with Bobby as our SRO read him his rights, handcuffed him and placed him inside the police car. I asked him if he would be OK, but his eyes had taken a dark sheen and I knew I had lost him. I walked back in the building and cried. This certainly didn’t feel like the best thing for him. How many kids do we have to lose before we can create schools where students want to be? I failed Bobby that day and feel that our system failed him too.

Ryan Fear is a high school dean of students in Oregon.