The Day I Wasn’t Afraid To Fly

7 min readSep 17, 2020

“Songs are as sad as the listener.” ― Jonathan Safran Foer

After I was sentenced in federal court, I went through transit from a county jail to the federal system. Sometimes called “diesel therapy,” the process involved going through a central processing facility, similar to the distribution networks of Amazon or FedEx, except with human beings. Most people ended up going through Oklahoma City where they were then bused or flown to their final destination.

Getting to Oklahoma was an arduous process. I went from two jails in Wisconsin, to another federal prison in Indiana, and then finally to Oklahoma. On the way to Oklahoma, our bus broke down in Missouri and we were all concerned that they’d take us back to Indiana and leave us in limbo. It was a hot summer morning and we were all pretty weary from the confined and shackled ride. Thankfully there was another bus at a prison only an hour away that the US Marshals had radioed to come pick us up. When the second bus arrived, they parked the bus doors so that the buses were head to head with a little bit of room to depart one bus directly into the other. The Marshals surrounded both sides of this small chasm, shotguns at the ready. The message was clear: make a break for it and it’ll be your last.

There was a moment on that bus that I will never forget for the rest of my life. The guy sitting next to me started to make conversation and asked me how much time I had. “Five years,” I said. I took his invitation of conversation as an opportunity to vent. “The judge really fucked me over,” I complained. I proceeded to let the anger of the past few months come rushing back. After unloading my diatribe on him, I asked him where he was going. “From Oklahoma I’m going to Ohio. They’re bringing up old charges against me from 1992,” he said casually. Thinking out loud I said, “1992? That’s 21 years ago! What about the statute of limitations?” He looked at me indifferently and said, “Not for murder.” I paused, dumbfounded. Duh, why hadn’t I put two and two together? Here was a man who had been locked up for over two decades. Even if he miraculously beat the new murder charge, he would only get to celebrate that victory by going back to federal prison for the rest of his life. And yet he had a cheerful demeanor; telling me he was looking forward to the change in scenario in Ohio and going back to court. I was silent the rest of the bus ride. How could I be upset right now? I’m the one with a release date. For the rest of my sentence, anytime I felt the urge to complain I would pause and remember this conversation. It gave me the humility to realize two things. One: before you give energy to the complaint, remember the suffering around you. Two: even with a life sentence people can still find meaning, can still laugh, and can find stillness and beauty in this life. There is only one real prison, and that is the prison of the mind.

After corralling us into the second bus, we finally made it to Oklahoma City several hours later. I was exhausted from the nearly 24 hour bus ride fiasco. As soon as we were processed in, the guards passed around some paperwork that we needed to fill out. I looked at some of the questions and the gravity of the situation hit me. One of the questions asked to write in our next of kin should we die while in custody. It occurred to me that there were people next to me filling this out who knew that they were never getting out. Even more heartbreaking, there were people next to me filling it out who thought they would get out but would die before their release date because of illness, suicide, or violence. That shit really hit me.

The transfer facility in Oklahoma was an interesting environment. Because it was a central processing facility, inmates from all over the country would arrive at all hours of the day. Guys who had been down 20 or 30 years might reunite with a friend from an old prison they hadn’t seen in years or decades. Cellmates were a dime a dozen. People came in and left at all hours of the day. I’d wake up with a cellmate, go to sleep without one, and sometimes wake up with a new one. It was a chaotic environment in that regard. One had to be vigilant to size up new cellmates and the emotional temperature of the tier, lest you get caught off guard.

I spent a week in Oklahoma awaiting transfer to my final destination in Pennsylvania. Due to security, you don’t actually know when you’re leaving the facility. It could be days, weeks, or months. At some hour in the early morning a guard would knock on your door and tell you to get ready. After talking with several inmates earlier in the week, I knew that I would be taking a plane — the infamous Con Air — to my prison in Pennsylvania. From the main cell block, at least 100 of us were led down a long corridor to a jet bridge that was attached to the facility leading to the Oklahoma City Airport. Because of multiple tornadoes in the week prior, it had been severely damaged and unusable for our purposes. As a result, we were going to have to walk on the tarmac to board the plane from the back.

When the Marshals had secured the perimeter of the plane, we were told to walk in a line — cuffed, black-boxed, and belted — to the back of the plane. When I walked through the door onto the tarmac, the scene was surreal. I hadn’t been outside in four months and it felt good to get some fresh air and look around. What I saw was intense. Dozens of Marshals were all over the tarmac with a mix of shotguns, rifles, and pistols ready to shoot any one of us should we decide to pull something ambitious.

When I finally got on the plane I watched as they loaded us to the hilt, including a few female inmates that they escorted to the front of the plane. The plane itself looked like a stripped out 737 that made questionable engine sounds. Normally I had a pretty big fear of flying whenever a plane would take off. But on that day as the plane was taking off and I was staring at a Marshal’s pistol a foot away from my face, I thought, you know what, if this plane crashes so be it. The anxiety that I usually felt when a plane was taking off was gone. As we got into the air, the lights were flickering all over the plane and the engine sounded like it was going to explode. I couldn’t help but feel dazed and in disbelief. Is this really my life right now?

From Oklahoma City our first stop was Atlanta. Having flown through Atlanta several times, it had never occurred to me that thousands of federal inmates were processed through there on a weekly basis. After landing we rode past all the civilian terminals and stopped near the cargo and military planes some distance away. I watched as the Marshals secured the perimeter again to escort some of the inmates on the plane to the detention center in Atlanta. I thankfully did not have to get out of the plane, and within an hour we were on our way to our next destination.

It’s interesting flying in a plane when you aren’t told where you are going or how many stops until you can get off. It adds a layer to the journey knowing that it will most likely be a long day no matter what. Lucky for me, the next stop in Pennsylvania was my stop. Something I took for granted at the time was the warm summer air as I stepped off the plane. Later in my sentence I would hear many awful stories of guys waiting on the tarmac in the freezing cold in just a t-shirt while the Marshals took their time.

Weary from the 18+ hours of transit and shackles, I finally reached my destination after an hour bus ride from the airport. The journey of my new life in the federal system was about to begin. And as strange as it sounds, it felt like freedom walking into that prison. I’d been in solitary confinement in the weeks prior to Oklahoma, and the jails I was in prior to that didn’t let us go outside at all. It was my first day outside without handcuffs and I loved it. In jail I worked out in my cell using my laundry bag as a weight. Now I had access to a full weight pile and recreation yard. Even the food was better, and I was grateful for the difference.

All of these silver linings remind me that perspective is everything. I remember seeing guys who’d been dragged to the US from some third world country only to experience it’s prison system. Their attitudes couldn’t have been more different than a lot of the Americans. For some of them, their living conditions were an upgrade on their life on the outside; both in terms of consistency and quality. Some seemed genuinely at peace with their present circumstance. None of this takes away from the injustice of American incarceration, but it is a nice reminder that there are many paths of perception when it comes to individuals in the same environment. It is a testament of the human will, and a reminder of the choices we make when we interpret the external world around us.