Creative Commons License

Republish our articles for free, online or in print, under a Creative Commons license.

Photo by Ant Rozetsky on Unsplash

As I approached Watkinson House on my first day out of prison in Hartford, Connecticut, I saw there was a large group of guys hanging out in the parking lot. 

It was summer so they were all wearing baggy shorts, long t-shirts, flat brimmed baseball caps and Nike Air Force Ones. I recognized the uniforms. They were probably on a cigarette break before they hustled back inside to watch a few more hours of mind-numbing television.

The front porch smelled like old wood in need of a paint job, but the door had a very modern surveillance system. I pushed the buzzer and looked up into the camera.  A businesslike yet gentle woman’s voice asked me if she could help.  

I quickly rifled through my now institutionalized brain for the shortest and most succinct answer possible. “New resident,” I replied.  

The door buzzed open and I stepped inside. To the right, another large group of men sat in a dayroom watching television. The office was to my left where two women sat behind a counter. I introduced myself and presented them with my papers and my bag of clothes.

The familiar process started all over again. There were forms to fill out and drug tests to take. I had an initial meeting with a counselor. They searched my bag and my body — aerosol containers, sharps, electric shavers and alcohol-based products were either discarded or tagged and stored.  

Once processing was completed, I was escorted up to a room up on the third floor where I would have three roommates; I was assigned an upper bunk and given a supply of sheets, blankets, towels and basic toiletries — I was an old pro at this already.  

I started to make my bed when my first roommate walked in — a bald Latino man named Hector. He looked pretty tough; his arms were sleeves of gang tats. He looked me up and down, and then asked if I was a cop. I said no, and then I asked him if he was a cop. He smiled. I think he liked my response.  

I could also tell that he was stoned. When my other roommates showed up, it was pretty clear that they were all stoned. Hector pulled out a bottle of some cheap liquor, and they all got drunk right there in the room. I suppose that they had a right to be suspicious when I didn’t drink with them, even after I told them that I would be five years sober in a few weeks.  

Nonetheless, Hector — stoned, drunk and barely able to speak — had an idea: He had a few tests to put me through to prove I wasn’t a cop.

Hector asked me if he could continue to store his cell phone and charger in a hole in my mattress. He had been storing it there while my bunk was unoccupied. We both knew that cell phone possession charges were among the most egregious offenses in prison.  It wasn’t a big leap to guess that they weren’t allowed in the halfway house either and that we could get sent back to prison if we were caught.  

I told him to forget about it — I was White, not stupid. He seemed delighted with this response.  

For his next test, Hector took off his shirt, exposing his hairy tattooed body — he explained that he liked to shave his body hair so that his chest and back were smooth.  He proposed that I shave the hair off his back.  

I figured that this was my Mendoza Line — I was in a halfway house my first night out of prison about to shave the back hair off of a Latino gang member. When I was finished, we wrapped our arms around each other and laughed.  

He pulled a big plastic box out from under his bunk and showed me a huge cache of sundries. He was running a bodega for the benefit of the guys who couldn’t get passes out of the house. Of course, he marked them up two to three times their cost. 

“Go ahead, Papi,” he said. “Take one. No charge.”

I went for the Old Spice push-up anti-perspirant stick. Things went pretty smoothly with Hector from that point on.

The halfway house had a culture unto itself, but with none of the checks and balances of prison. Quickly dissipated was the prison culture that honored respect.  

For example, in prison, if I were in the television room and put my book down on my chair, nobody would have touched it for hours. At Watkinson, my book was pushed onto the floor and I found a guy sitting in my seat.  

In prison, phone calls were automatically cut off after 15 minutes. In the halfway house, guys hogged the phones for hours even though there were lines of other guys waiting.  

In prison, meals were served in a line and doled out somewhat systematically. In the halfway house, it was a cattle call of first come, first served. I wound up eating a lot of cereal and peanut butter those five weeks. 

Watkinson House did however have Alcoholics Anonymous meetings most nights and took us to even more meetings in the van. Fortunately, as a federal client, I was eligible for a pass in three days (it took Connecticut clients 20 days to get a pass). As soon as I was issued a pass, I could go outside on my own.

I had not been on a computer in 14 months. I was hoping that I’d at least have some email. I met with my counselor to find out how and where to do that because there were no computers available to clients at the halfway house. 

The only place that she could think of was at the state’s employment agency, called CT Works, which was a pretty long bus ride from downtown. Clients who achieved level four status were allowed to go to the public library downtown and use the computers there, but I was short-termer and only had a level one status.

I received instructions for a pass and then filled out a request. I explained exactly where I wanted to go and why, including the address and phone number I got from the Yellow Pages in the office. My pass was approved, so on my assigned day after breakfast, I was handed a three-hour pass — barely enough time to accomplish my mission – along with directions to CT Works at the edge of the city. I walked out the door of the halfway house feeling like a free man. 

It was my first taste of freedom. The one-mile walk to downtown felt great. I caught my first sight of the Connecticut state capitol, a rib joint, and the arena where the Hartford Whalers used to play. But mostly there were people, real people, and they were going to work, wearing work clothes and sitting on benches eating breakfast. 

I got to the center of the city and found the bus stop on Main Street in front of the State House where I would catch the No. 40 bus to CT Works. I asked a few people in line to make sure I was waiting for the right bus — with only a three-hour pass I didn’t have any room for error. They were very kind, especially given that I was dressed like a guy only a few days out of prison.  

It took about a half hour to get to CT Works, located in a large factory building that had been restored and repurposed into a business incubator housing all sorts of services for poor people. I had to register to become a client and then wait in line for a computer.  By the time I finally got on a computer, two hours had passed since I left Watkinson House, and I was worried about getting back in time. I logged on to my Yahoo account and saw I had lots of spam but no messages.

Now I had to hustle. The bus stop for the No. 40 bus back downtown was across the street. Every minute seemed like an hour, as I waited for that bus to come from Windsor back into Hartford. 

Time seemed to slow down as I thought about the repercussions of arriving at the halfway house late. When the bus got downtown, I still had 20 minutes to walk up the hill back to Watkinson House. But the bus had let me off on Main Street in front of a Burger King.  

The poster with an Oreo shake in the window looked so good it practically had my name on it. I knew I was not supposed to stop anywhere unless I had a pass for it. But it was as if my body had a mind of its own. I couldn’t help myself. I found myself in line ordering the biggest shake they had. 

Soon, I was walking up the hill and slurping down my shake. At the corner before I got back to Watkinson House, I licked the last drops off the straw and threw away the remnants in a dumpster behind one of the housing projects. 

I walked into the house on time and the women behind the desk were practically falling out of their chairs laughing. I asked if everything was okay.

One of the women commented that it was a good thing I was leaving in five weeks — I would never make it there if I couldn’t figure out how not to not to drink a Burger King shake on the streets without a pass. She said at least five people saw me.  

The blood drained from my face. I was busted. Was I going to go back to prison over a milkshake?  

She told me to relax, the feds were way too busy to bust guys over something like this, but she also gave me a warning. They sometimes take away the people they don’t like for the smallest infractions. The people they like, they leave alone. 

She turned out to be right. In my five weeks there, there were shakedowns where they would overlook stuff from some guys, but handcuff and take away others.

Disclaimer: The views in this article are those of the author. Prison Journalism Project has verified the writer’s identity and basic facts such as the names of institutions mentioned.

Jeff Grant is an ordained minister with more than three decades of experience in crisis management, business, law, reentry, recovery and executive and religious leadership. As a formerly incarcerated individual, his work is dedicated to helping people move forward in their lives. Grant's New York law license was recently reinstated and he was featured in The New Yorker magazine. Grant hosts a weekly online White Collar Support Group, is the host of the White Collar Week podcast, and serves as editor of