In “A White Man’s Guide to Rikers Island,” Another Man’s Shoes Is Uncomfortable

“The biggest deficit that we have in our society and in the world right now is an empathy deficit. We are in great need of people being able to stand in somebody else’s shoes and see the world through their eyes Barack Obama

It is oft said that until you have walked in another man’s shoes or traversed in his path, you can never understand the pain, the fear, the angst, and the life choices. In Richard L. Roy and Eric C. Webb’s “A White Man’s Guide to Rikers Island” race, class, privilege, and the criminal justice system is examined through the lens of a white man incarcerated among mostly African American and Latino inmates.

Mostly a one-man show, Richard L. Roy tells his real-life story of killing a young Hispanic man in a car accident while under the influence of alcohol and cocaine in the mid-1980s. Sentenced for involuntary manslaughter to the infamous Rikers Island, Roy must navigate the criminal justice system, as well as the particular culture of prison life at Rikers.

Roy tells an incredibly poignant tale of what it is like to be a white man imprisoned at Rikers where the inmates are overwhelming of color, poor, and uneducated. This incredible tale of self-discovery and insight gives a bird’s eye perspective on a broken criminal justice system that victimizes folks with no money, no education, and no white privilege.

Along the way, Richard L. Roy, portrayed exquisitely by Connor Chase White as the incarcerated Roy, comes up with a white man’s guide to survival at Rikers punctuated by prison lingo and slang that is key to making it behind bars. Roy not only distills incredible information about prison culture, but also examines historical and empirical evidence of race bias and class distinctions that establish who ends up doing time in the US prison industrial complex. (Note: African Americans make up roughly 12 percent of the US population, while making up 92 percent of inmates at Rikers Island.)

Though Roy’s stint at Rikers is short—only six months—his insight into white privilege, race and class is worth more than many academicians who’ve spent a lifetime of study on the subject. Perhaps, the most intriguing aspect of this show is Roy’s interaction with his fellow inmates and guards. Roy does a deep psychology plunge into the characters of the inmates he conjures up, particularly, the pre-op transsexual who is kicking a heroin habit but has the wisdom and compassion of great sages.

Images courtesy of Spin Cycle

Sadly, very little has changed at Rikers since Roy’s incarceration in the 80s. And with the recent death of transsexual Layleen Cubilette-Polanco in June of this year highlights that much needs to change at Rikers and with the criminal justice system as a whole.

“A White Man’s Guide to Rikers Island” was originally intended to run for seven weeks starting on July 17. But due to popular demand has been extended to September 26.  “A White Man’s Guide to Rikers Island” is at the Producer’s Club. For more information, go to

—William S. Gooch

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