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How the prodigal son became a preacher

Derrick Holloway in the chapel at San Quentin in 2013
Nigel Poor
Derrick Holloway in the chapel at San Quentin in 2013

KALW has partnered with radio producers inside California's oldest prison to bring you the San Quentin Prison Report, a series of stories focusing on the experiences of these men, written and produced by those living inside the prison's walls.

Derrick Holloway grew up in a Christian family, but chose to sell drugs and participate in a lifestyle that resulted in him committing a murder. After being convicted and sentenced to life in prison, Holloway eventually went back to the Christian faith he was raised with. In fact, he became a pastor and began preaching the word of God.

It's Sunday morning in San Quentin's Garden Chapel. Derrick Holloway, an inmate preacher, gives a sermon to the congregation.

“No matter what you are going through,” he says, “no matter how hard, no matter how difficult … You should never give up because you receive so much mercy -- so much we should all be in a grave.”

Holloway theatrically walks up and down the aisle, playfully entertaining the crowd. He seems born to do this. But this isn’t the life he has always lived. Although he had a stable upbringing that revolved around family and church, at the age of 15, his mind started to wander.

I started to, you know, be attracted to things that was outside of the home that was more glamorous,” he says, referencing how he saw others living out street life. “And I wanted that fame, the fortune, you know what I mean? All of that stuff that came along with it.”

For Holloway, it was an exciting life. “I thought that the kind of life I seen exemplified by momma and daddy -- I was like, ‘Man, that’s boring.’ I was like, ‘Man, I'll deal with that later on in life when I get older,’ you know?”

Still, Holloway stuck with school, and even ended up playing basketball for Miles College in Alabama. But although he loved the sport, his desire for money was much greater.

Soon he was getting phone calls from people urging him to get in on the game. “So the next thing I know I quit school, quit the basketball team and went back to California,” Holloway says. “I started learning some things about the drug game, and started learning some things about the street life, that just did more to influence me to go into the wrong direction.”

The drug life that he thought would bring him fame and fortune also came with a dark side -- one that eventually caught up with him. In 1997, Holloway was sentenced to 37 years to life for first-degree murder and robbery.

Holloway is convinced that God had to intervene in a dramatic way. “When you live that kind of life, this is the end result, whether dead or prison. It's the same thing; there is a loss of liberty,” he says. “So coming to prison for murder was just par for the course because I had really gotten off track. So it took prison to say, ‘Stop: Take a look at your life.’”

Soon after his incarceration he began reflecting on his life, and knew he had to make a change. This ultimately brought him back to the roots of his spiritual faith.

Holloway says that being locked in the cell forced him to confront himself. “I had to really face what I had to do. The first thing I had to do was ask both my mother and father to come visit me,” he says. “I wanted to assure them that they did everything that they could, that the choices I made were the choices I made.”

Not long after reconnecting with his parents and spiritual upbringing, he says he experienced a calling. It wasn’t necessarily one he would have chosen, he admits.

If it was up to me I would have just been a pew warmer,” he says. “However, God began to speak to me about things, about life issues, about the church, about society, about our community and saying you know look at this. And so something began to be birthed in me.”

And that's when, to the surprise of many, Holloway became a preacher.

It was certainly a surprise to his friends. "I never would have imagined that you'd be carrying that Bible, man,” they’d say.

“Some of them were childhood friends that knew me growing up and seen my illicit activities,” Holloway remembers. “And so to see me now it's really testament to God -- not to myself ... We just have to be willing to be changed.”

In the Bible, there is a story about a prodigal son who left the loving care of his father and began living a reckless lifestyle. In essence, Holloway’s story can be compared to that one. And if you ask him, that’s how he tells it, too: how he left a stable life under the roof of a Christian father for a life of chaos. Ultimately he had to return home and ask for forgiveness.

This is the latest installment of the San Quentin Prison Reportradio project – a new series that brings you stories produced by men currently serving time in California’s oldest prison. You can listen to more stories from this series at www.kalw.org.

Crosscurrents San Quentin Radio