Derek R. Trumbo, Sr.

Derek R. Trumbo, Sr.

Derek R. Trumbo, Sr., a multiple-time PEN Prison Writing Award winner, is an essayist, playwright, and author whose writing has been featured in "The Sentences That Create Us: Crafting A Writer's Life

44 posts
color digital collage on a light teal background with torn paper lines that look like waves. eight birds fly from the bottom
Crime, Reform & Abolition

Never eat the candy on your pillow: Hope lies in the rubble

Dear Reader, Imagine everything around you is in flames. There is smoke billowing up from the dorms, and the academic building, medical unit, library, and commissary are all ablaze. Picture incarcerated people running wild and wreaking havoc with their faces covered in towels and T-shirts.  Now, place yourself behind the

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5 Min
By: Derek R. Trumbo, Sr.
color digital collage of a cat's and several flying birds' silhouettes in front of dark teal cross-hatching on a light teal b
Crime, Reform & Abolition

Never eat the candy on your pillow: Born free

Dear Reader, Many children collect dolls, teddy bears, or other stuffed animals to make their lives feel comforting and complete. My sister had tons of dolls, including more than 20 plush Garfield dolls. Her favorite was a Garfield doll with a bowl of spaghetti over his head. My favorite was

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4 Min
By: Derek R. Trumbo, Sr.
color digital collage on a teal background of a minimalist drawing of Black man with a fade. squiggly darker teal lines stret
Crime, Reform & Abolition

Never eat the candy on your pillow: What hurts more?

Dear Reader, If imprisonment were a legal thriller, one of the most dramatic scenes would be the courtroom as the guilty verdict is read. Mothers would burst into tears, lovers would plead their undying love, and the person found guilty would take their walk of shame amid cries of, “You’

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5 Min
By: Derek R. Trumbo, Sr.
digital collage on a teal background of a piece of paper with circular scribbles on it
Crime, Reform & Abolition

Never eat the candy on your pillow: Breaking the cycle

Dear Reader,  When I came to prison nearly two decades ago, I believed my life to be completely over. Everywhere I looked behind the fences, there were broken people living broken lives. It was a cycle of brokenness. Prison isn’t a fix to anyone’s problems.  But the further

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5 Min
By: Derek R. Trumbo, Sr.
color digital collage of a hand holding up a skull on a teal background
Crime, Reform & Abolition

Never eat the candy on your pillow: Circle of trust

Dear Reader, “To be or not to be?” Hamlet famously asked this question in the play by the same name written by William Shakespeare. I first encountered the life-changing power of Hamlet when I signed up for a prison playwright’s circle called Voices Inside, created by Curt Tofteland and

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5 Min
By: Derek R. Trumbo, Sr.
color digital collage on a teal background with an analog circular wall clock
Crime, Reform & Abolition

Never eat the candy on your pillow: Release 

Dear Reader, This week’s subject is release. When I first stepped foot in prison, it felt like my life ended. What would release feel like? Would leaving prison be like a new beginning? Prison has a way of distorting time. Days become weeks that feel like years. Waiting on

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5 Min
By: Derek R. Trumbo, Sr.
color digital collage on a teal background. a black-and-white cutout photo of an open mouth is in the center with a black tex
Crime, Reform & Abolition

Never eat the candy on your pillow: Anger management 

Dear Reader, Prison teaches many valuable lessons. If you don’t have tools in your toolkit, such as patience, understanding, and empathy, you will—if given enough time. Prisons and their staff have ways of testing your patience, exhibiting next to no understanding, and for the most part utterly lacking

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5 Min
By: Derek R. Trumbo, Sr.
Never eat the candy on your pillow: Rewriting your life one character at a time
Crime, Reform & Abolition

Never eat the candy on your pillow: Rewriting your life one character at a time

Over time, I’ve realized that every setback can become an opportunity to rewrite our problems into solutions

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5 Min
By: Derek R. Trumbo, Sr.
digital collage on a light teal background with a drawn image of a tablet with black circular scribbles at the center
Crime, Reform & Abolition

Never eat the candy on your pillow: Technology and the imprisoned

Powerlessness impacts every aspect of an incarcerated person’s life—including the use of technology

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5 Min
By: Derek R. Trumbo, Sr.
hand-drawn pencil illustration of a hand holding a pencil up for perspective in the foreground against a man sitting with his
Crime, Reform & Abolition

Never eat the candy on your pillow: The artist’s hustle

Art gives incarcerated people a chance to create something beautiful and unique in an environment that cultivates monochrome sameness

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5 Min
By: Derek R. Trumbo, Sr.
digital color collage on a watercolor teal background with strips of torn text-covered paper. black-and-white images of an op
Crime, Reform & Abolition

Never eat the candy on your pillow: An introduction to prison hustles 

Prisons provide bare-minimum living conditions and insufficient pay, forcing people inside to find alternative ways to make enough money to survive

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5 Min
By: Derek R. Trumbo, Sr.
color digital collage of a teal background with white and brown torn paper strips at the top and two black-and-white images o
Crime, Reform & Abolition

Never eat the candy on your pillow: Friend or foe?

Loneliness can make people vulnerable to exploiters, and prisons are deeply lonely places

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5 Min
By: Derek R. Trumbo, Sr.

Showing 12 of 44 total posts

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