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Houston Matters

Comedian Ali Siddiq Spent Six Years In Prison And My Stepdad Was His Guard

Houston Matters producer Michael Hagerty talks with Siddiq about the relationship between prisoners and guards.

Comedian Ali Siddiq poses with Houston Matters producer Michael Hagerty. During their interview, the two discovered Hagerty’s stepfather was a guard at the prison where Siddiq was incarcerated in the 1990s.


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Comedian Ali Siddiq spent six years in prison in Texas. He often mentions it at the beginning of his act.

But only recently did he talk about it in-depth on stage — first in a story about a prison riot on the Comedy Central series This Is Not Happening.

And he recently recorded a comedy special in the Bell County Jail in central Texas, called It’s Bigger Than These Bars, which was also released as an album.

In the special, he performs in front of a group of inmates and also sits down with smaller groups of incarcerated men and women in their cells to hear their stories.

So, when the Houston-based comedian came to Houston Matters to talk with me about those projects, I didn’t expect anything too out of the normal. But I was interested in hearing his story.

Little did I expect our stories would intersect.

Something Mentioned In Passing

As a journalist, I’d been taught the conversation isn’t about the interviewer. The focus is the guest. But, in an instant, this one veered straight for my front door.

About 40 minutes into our recorded conversation, Siddiq mentioned in passing that he’d spent time in the Torres Unit in Hondo, Texas. That’s outside San Antonio.

I felt a jolt and had him back up.

“Did you say Torres Unit?” I asked.

A mock booking photo from comedian Ali Siddiq’s stand up special, It's Bigger Than These Bars, which was recording inside a Texas jail.

I hadn’t thought about that name in years. And, in interviewing a former prisoner, I wasn’t even thinking about my own tangential connection to the Texas prison system: when I was just ten, my mother married a man from Texas who was a prison guard. Bill Strickland.

We were living in northwest Indiana, where I was born. And, without a real understanding of the heat and humidity that awaited us, we chose the month of August to move to Greater Houston. Specifically, we landed in the small town of Sweeny, near Lake Jackson, where we stayed for a few years.

Needless to say, the sadistic heat, the turtle-sized cockroaches, and the relational challenges embedded in the stepchild-stepparent dynamic made for some intense culture shock.

Then, just as we were starting to adjust, the Texas Department of Criminal Justice transferred Bill to the brand new prison in Hondo. So we moved again.

Worlds Colliding

Comedian Ali Siddiq in the Houston Matters studio.

Flash forward 26 years to a recording booth at Houston Public Media. After a few follow-up questions over an accelerating pulse, I was stunned to discover not only did my stepdad and Siddiq spend time on opposite sides of the bars at the same prison, but they were there at the same time. And Siddiq remembered him.

I explained to him what my stepfather was like. How sometimes our relationship was quite challenging for me. How I gave him credit for taking on the financial burden of two children that weren’t his. And how I knew Bill cared for us and our mother on whatever level he was able, in whatever way he was able.

So, I asked Siddiq what he remembered about Sgt. Strickland.

“Being a guard,” he said, laughing.

When I pressed him about how my stepfather may have treated him, Siddiq said he remembered Sgt. Strickland simply doing the kinds of things all the guards did, like overturning an inmate’s cell from time to time.

A Very Different Conversation

A prison guard on watch at the Connally Unit near Kenedy, Texas.

From there, a suddenly personal conversation ensued about the relationship between Texas prisoners and their guards.

Just minutes before, Siddiq was a stranger to me. He was telling me how humor helped him survive incarceration. How it was useful in diffusing potentially violent conflicts behind bars — sometimes between inmates and sometimes between himself and guards. And how he turned all that into a very successful career outside.

But now, as he recounted, for instance, some of the ways inmates used to razz guards about their wives “wearing the pants” at home, the wife in the anecdote was my mother. The guard was my stepfather. Bill.

TDCJ correctional officers in uniform.

I’m pretty sure Bill hated being a prison guard. But, as Siddiq says in our interview, at least he got to go home at the end of each day and eat whatever he wanted. And when my stepfather ate those meals, I was often sitting across the table — maybe getting into a needless argument about which utensil I used to eat my peas.

A few of the unsavory conclusions he’d made about the world, which he’d sometimes share at home, surely had to be influenced by what he heard and saw day in and day out from the people on both sides of the bars at the Torres Unit.

And one of those people was Ali Siddiq.

I remember one time in my early teens sitting in the car with my mother outside the Torres Unit. We’d brought Bill his lunch, which he’d forgotten at home. From the parking lot, I peered through the curling razor wire and chain-link fence at the sterile, white buildings. Who knew Ali Siddiq was on the other side. Who knew that a quarter century later he and I would sit across a table of our own proving Bill wrong.

You can hear Michael’s conversation with Ali Siddiq in the audio above. Siddiq is currently a finalist on NBC’s comedy competition show Bring the Funny.

Comedian Ali Siddiq.