Sheridan Prize for Art

The 2021 Sheridan Prize for Art Archive

Tommy Winfrey


For most of his life Tommy let other people and the world define him, but today he chooses to define himself as an artist.Art helped Tommy to transform his life. Painting became an extension of his being allowing him to express himself. Painting also allowed him to see the world through a critical eye, and when he turned that gaze inward, he learned a lot about himself.

Through self-expression, Tommy has come to recognize both his weaknesses and strengths. He developed a sense of belonging, and he learned to show up in life. Something he had a real problem with in the past. Tommy considers art to be a passion of his, something he kept buried within his soul for way to long. He consistently felt like he very little sense of choice growing up. He felt there were always so many rules to follow, so he would often break them. This got him into a lot of trouble, and at the age of 19 years old he began a life sentence in prison.

Art allowed Tommy to see that although there may be rules it was really about how he applied them to his life. He realized the paint, the brush, and the canvas are all controlled by the laws of physics. Instead of feeling trapped by this realization, he decided to accept them for the way that they were. He saw that he needed to learn to operated within these laws, be creative, and he found the processes that allowed physics to work for him.
It was simple, all he had to do was show up and start thinking for himself.
Since Tommy’s release from prison, he has gone on to work on justice system reform, while also still practicing his art. He has had gallery showings in San Diego.


Sacramento State University – Executive Fellow
San Diego State University – BA in Criminal Justice


Ray at Night – 2018
Hype @ the Studio Door – 2018
Tedx San Quentin – 2016
Luggage Room Gallery – 2014
Yerba Buena Center for the Arts – 2014
Marin Humane Society – 2014


PEN America Prison Writing Contest, First Place Memoir Category – 2016

Tommy Winfrey

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