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It was a life altering experience. The absolute worst part was the loss of my freedom.

“Be strong!” said my brother as I was led out of the courtroom. I had just been sentenced to 90 days in the county jail for possession with intent to sell. I had hired the best attorney I could find, and had received a light sentence for the felony I had committed. Having my father, in his Navy Captain’s uniform, with me in court certainly helped.

I had been a lousy cocaine dealer. Really, I was not so much a dealer as a college kid with an expensive coke habit. If you worked in Coronado’s top restaurants in the early ‘80s, you were exposed to coke on a nightly basis, but especially Fridays and Saturdays. Closing time would come around, and the real dealers would show up at the bar, pockets full of weighed-out product. I’d buy an eight ball, break it up, and sell it to my fellow SDSU students at parties. I snorted up every bit of profit I might have made — “Don’t get high on your own supply” was a rule I did not follow. One night, I was out on El Cajon Boulevard, out of my mind on coke and planning to go surf Trestles at dawn, when a cop pulled me over and noticed a jar in the open space between the seats. “What’s that?”

Thankfully, I was placed in the jail’s “trustee” ward, which seemed to house the less dangerous criminals. Men with too many DUIs, men in for drug possession and sales, white collar crimes, etc. There were probably 100 of us in the trustee ward, and we had it much better than other inmates: TVs, ping-pong, and generally fewer rules and restrictions. And jobs. Jobs in jail were highly sought after, as they kept you out of trouble, and you would always have money “on your books” to buy cigarettes or candy or hygienic essentials.

Because I had been a waiter at a Coronado restaurant, I was employed in the ODR (Officers Dining Room), a plain square room with windows, maybe ten tables, and stainless steel kitchen equipment. I was basically a busboy for the guards; I would bring them food, drinks, and silverware, and clean their tables when they finished. Many of those guards were nice, and would chat me up from time to time. They seemed to really care, and wanted me to get my life straightened out and for me to make something of myself. One in particular, a guy named Prendergast, would often say, “You don’t belong here.” Other guards were not so nice; they seemed bitter, and did their best to make things uncomfortable for me and the other inmates — as if they were looking for a fight.

During any particular meal shift, I was the only inmate allowed in the ODR. But when the room was empty, and I was cleaning up or making iced tea, inmates would pop their heads in the door and ask for things. “Hey Holmes, get me a bottle of hot sauce.” I declined all such requests: one infraction would cause me to lose my job in the ODR, plus my bunk in the trustee ward. I’d be “rolled up,” transferred to a less desirable ward in the jail, with much worse offenders for company and no amenities whatsoever.

I declined requests, yes — but that doesn’t mean I never took risks. I soon realized there were politics and hierarchies in jail that went beyond where you slept. The guy who ran the laundry had a great job; he washed and handed out clothes to every inmate in the trustee ward. “Luis” was a short stocky Hispanic, covered in tattoos; not the kind of person you’d want to cross. Early on, he pulled me aside: “Listen Holmes, here’s how it works here. You scratch my back, I scratch yours. You bring me some hot sauce when I ask, you get the cleanest clothes that are perfectly starched and pressed. You will also stay on my good side.” I was okay with his proposal, especially the “good side” part.

Luis was even kind enough to give me smuggling instructions. While at work in the ODR, I would make iced tea in large plastic containers that must have held five gallons of liquid. If I made the tea dark enough, you couldn’t see the bottle of hot sauce rolling around on the bottom of the container. This tea was popular in the trustee ward, so I made it almost every day. I’d put three or four containers of tea on a rolling cart, walk the cart past the laundry room, and my new compadre Luis would reach his hand in, grab his hot sauce, and give me a set of clothes so clean and pressed, you’d think I was going to a wedding. This was how jail life worked. Give and take. Money was hard to come by, so cigarettes functioned as the standard currency. Everybody seemed to smoke, as there was nothing else to do. I saw violent fights over cigarette debts that weren’t paid.

I assimilated quickly, and was able to make friends with some of the popular and powerful people in the trustee ward. There were groups and cliques: Mexicans hung with Mexicans, blacks with blacks, whites with whites. But I had friends in all the groups. My years of waiting tables helped me read the room: I could spot the nice guys, the sketchy guys, and the scary guys, no matter what color they were, and that proved beneficial.

I was also a very good ping-pong player, and we would have tournaments that gave the inmates something to bet on. This wasn’t family-friendly ping-pong. This was knock down, drag out ping-pong. I entered jail with a brand new pair of Adidas Superstars, and wore them out in 30 days. “Pack of smokes on the white dude!” was something I loved to hear.

One of my ping-pong fans was a tall, young muscular Mexican guy named Ernesto. He was probably 6’6”, and would knock you out if you looked at him wrong. He liked to bet on me, and we became friends. Once, I was roughhousing with another inmate, “Juan,” who was known for getting in fights with the guards. Juan was getting rough, and had me in a pretty tight headlock. All of a sudden, his grip on my head loosened. Ernesto had him up against the wall, fists clenched, ready to pound him. “Leave the motherfucker alone!” he screamed at Juan. I said, “Thanks Ernesto, but we were just playing.” Juan never roughhoused with me again.

Our tournaments were well attended, and they would always end up the same way: me and a tall black guy named TJ, would battle it out for the trustee championship. He was better than me, but I think he let me win to keep the attention going. He was really funny, had a high pitched giggle, and became my best friend. He said he was in for pimping, but who knows? Nobody tells the truth in jail. (My other friend said he staged robberies in his home and then collected the insurance money, only to be ratted out by a buddy.) TJ took me under his sizable wing. He would point out the guards and inmates who were nice and approachable, and those who were not.

One day, out of the blue, a very large guard with an even larger chip on his shoulder marched into the ODR during my shift and barked, “Come with me. You’re getting rolled up!”

“What?” I replied, dumbfounded. “Why? I haven’t done anything wrong.”

“A knife was found in the C block, and it came from the ODR.”

“It wasn’t me, and I had nothing to do with it.”

This was major. Even a butter knife can be ground into a shank, which can then be used to stab another inmate — or even worse, a guard. And the guard had this much right: the only place a butter knife could be found was in the ODR, and I was in charge of it. Though I insisted I was innocent, the guard took me out of the trustee ward and put me in some part of the jail I had never seen, with inmates I had never met. I was shocked, pissed off, and a bit scared of my new surroundings.

I asked to talk with the head guard of the new block, and explained that I had nothing to do with an inmate having a butter knife. Something about my plea must have convinced him, because they sent me back to the trustee ward, and I got my ODR job back. Or maybe it was just that he knew the other guard was a complete a-hole. I still think that other guard was just trying to mess with me. A long time later, I heard that he was shot and killed in the East County while investigating a robbery or something.

I never saw any rapes or anything sexual, but there was a gay ward, and the inmates had to wear special wristbands that identified them as such. I did see many violent and bloody fights. Usually, it was inmate vs. inmate. Usually, for nothing more than a denied cigarette, a disrespectful comment, or people looking at each other the wrong way. The fights could also have been racially motivated, as it was rarely the same race fighting each other. The guards would also get rough with the inmates, especially the ones who liked to disrespect and provoke them. With some inmates, that seemed to be the reputation they sought: “Look at my swollen black eyes. I got my ass kicked by the guards.”

There were alcohol and drugs in jail. “Pruno” was a popular alcoholic drink. They made it in the same containers I’d use to make tea. But I’m not sure how they made it, and I never drank any. There was weed too, that I imagine was smuggled in by visitors. But it always smelled really bad, and I never tried that either. Getting caught would get you immediately “rolled up.”

I was released after 30 days. It was a life-altering experience. The absolute worst part was the loss of my freedom. I recall looking out onto Front Street, and just wishing I could be there walking with the other “free” people. I swore to myself I would never do anything to jeopardize my freedom again. The nice guards supported this resolution: they would ask what I did on the outside, and try to point me in a positive direction. The shit guards would say, “You’ll be back.”