If Connor Chase Stewart has any apprehension about sharing a stage, even momentarily, with Richard Roy, whom he embodies in A White Man’s Guide to Rikers Island, he doesn’t show it. Nor does the difference in their physiques hinder Stewart—the much older Roy looks like an ex-football player now, although he was a professional boxer and a sparring partner for Muhammad Ali, while Stewart has the lanky frame of a basketball player. Still, Stewart’s casual yet energetic performance makes him a relatable guide through New York City’s famous prison.
White Man’s Guide, by Roy and Eric C. Webb, details Roy’s experiences after he was convicted, at 22, of a DUI charge for running down and killing a young Puerto Rican man. At the time, he had everything going for him, including a beautiful girlfriend and a budding acting career. The morning following the accident he was to begin an important role on The Guiding Light, but his drink and drug-fueled celebration the night before cut it all short. With hindsight, he says:
Guys like me get a DUI when they’re young, then run for Senator. See, I was born a privileged white man in Jersey. In case you hadn’t noticed. The young Rich Roy, me, was raised in Sussex County, horse country, in a modern, but stylish, home with 2 bedrooms, 2 and a half baths, 2 car garage, and a golf course that came up to the backyard. I played golf and basketball. I bought a Camaro when I was 17.
Stewart navigates the various emotions skillfully: apprehension, worry, crushing disappointment, considerable arrogance, and an ultimate ruefulness. It’s a classic fish-out-of-water story. Initially, it’s hard to feel sympathy for a brash and privileged white brat, but the fresh-faced Stewart holds one’s interest, and soon he’s being taken down a peg, then another, and another.
It begins with a phone call to his father, who hangs up almost as soon as he hears what has happened. When he calls again, his father says, “We’ll make this go away.” It’s unclear if the first disconnection was because his father was disgusted at his son’s behavior or if he jumped on the case to find a fixer. But the words “Make this go away” echo in Roy’s mind. “Those are the words we white folk love to hear,” he says.
After his lawyer has pleaded Roy down to negligent homicide and a year in jail, the sentence at Rikers begins with a lecture, and again Stewart is an engaging, enthusiastic guide, making points with the statistics: “At Rikers 85 percent of the prisoners haven’t been convicted of anything,” he says. Rather, most are waiting to go upstate to other prison facilities. Rikers is meant as a way station. The baseline number of inmates is 10,000, but it can rise to 18,000.”
Roy is assigned to a cell with Shivon, a transgender drug addict. He is also somewhat befriended by Saddam, a sterner and brusquer inmate. Both are black, and they become allies. Stories of good luck and bad unfold. Roy had been hoping for a work-release program, but Mothers Against Drunk Drivers militated against it successfully. He faces danger from the Puerto Rican enemies he makes after he, Saddam and Shivon band together to sell contraband. But he becomes a celebrity when he writes humorous pieces for the Rikers Island newspaper.
The periodic lessons in prison slang are schematic tentpoles. “White Man’s Glossary Entry 4,” Roy notes. “Protective Custody. Noun: a ray of hope that, sadly, simply does not exist on Rikers Island. Sorry, white boy.” Director Thomas G. Waites hasn’t curbed Roy’s often strident polemical attacks on white privilege; they border on white self-loathing and become uncomfortable.
I got two guilts... First is for taking an innocent life. Second is the fact that I got the comparatively rosy end of the prison lollipop because of who, no... because of what I am. Rikers is for folks meant to be there under a year, yet hundreds of those guys are stuck there for years. And you know what they’re guilty of? Being black. Being Latino. Being poor. System ain’t right...
The writing is at its best when Roy and Webb focus on details, such as the sports, the boredom, the working out, the uneasy sleep:
I roll back over, trying to find some semblance of comfort. The din around us is maddening. People snoring, praying, tossing, turning, babbling, pissing, jerking off, scratching...
It’s a world that is worth experiencing, but only secondhand—especially with Stewart’s hero as guide.
A White Man’s Guide to Rikers Island runs through Aug. 31 at The Producer’s Club (358 West 44th St.). Performances are Thursday through Saturday at 8 p.m. and Sunday at 3 p.m. Tickets are $25, available by calling (212) 315-4743 or visiting awhitemansguidetorikersisland.com.