Pimping Ain’t Easy

Feature: Confessions of a 'Street Sense' newspaperman

Ivory Wilson
• June 8, 2013 5:00 am


Pfc. Ivory Wilson III was 17-years-old, a model soldier, and a virgin when he left the gates of Fort Riley, Kan., one night in 1974. When he stumbled back to base in the pre-dawn hours, he was drunk, high on cocaine and weed, $600 richer, and bereft of his chastity.

Before that night, he was a young Texas cowboy. For 20 years after, he was a pimp. Not a "pimp," as the word is loosely used in the current vernacular, but an honest-to-god, three-piece-suit, pinkie-ring pimp.

Wilson, 56, is cocoa-skinned, tall and thin, and usually wears a dapper hat that covers his bald pate. Glasses creep down his nose. He has a graying goatee.

Everything from his former life is gone now, save for when he smiles and the light catches his right front tooth—a tooth capped in gold and encrusted with four tiny diamonds.

Born in 1957, Wilson grew up in the little town of Cheeks, Texas, near the Gulf port of Beaumont, where oil drillers hit the first big "gusher" back in 1901.

"Oil country and cattle country, soft grass and rodeo cowboys," Wilson said.

Wilson’s father, also Ivory Wilson, was a champion bronco rider, and his uncles and cousins all rode bulls on the local black rodeo circuit.

"My dad only participated in black rodeos," he said. "The rodeos were segregated then. He worked on white ranches breaking their horses, but they wouldn’t let him participate in their rodeos."

He was in high school the first time he jumped on the back of a bull one night in Beaumont.

"Mom said I couldn’t go to the jackpot bull ride, but I snuck out anyhow," Wilson said. "Went and rode it, too. Damn right. That’s what made me a cowboy."

But war was calling. The newspaper in Beaumont listed all the young men from town who had been killed in action in Vietnam. A lot of them were older boys that Wilson looked up to.

He got into the Army at age 17, but by that time the war in Vietnam was just about over. Instead of Southeast Asia, Wilson was sent to Fort Riley, Kan.

"The military was loose back then—gambling, drinking, smoking weed, doing mescaline," Wilson said. "All of them were doing meth, even my C.O. It was wild. Everybody going to Vietnam and dying. No one cared about starched fatigues!"

The first thing his commanding officer told him was, "Don’t go downtown by yourself because a hooker will trick you into an alley and a pimp will kill you for your money."

Wilson didn’t drink or smoke, and he knew only about horses and cows, not pimps and hookers, so he stayed on post and worked on his pool game.

"For a whole year my buddies said, ‘Ivory, you shoot pool very well, you should come downtown and win some money from this pimp named Sam."

One night, Wilson finally gave in. He jumped in a cab with five of his Army buddies.


"You cats going on the whore stroll?" the cabbie asked them.

The cabbie was talking about Ninth Street, a two-block strip of Junction City full of bars and brothels, and a notorious haunt for war-bound GIs in the ’60s and ’70s.

"You might not come back, so everybody was buying pussy before they go to Vietnam, and everybody coming back was still buying pussy," Wilson said.

The cab turned the corner onto the Ninth Street strip. Wilson saw hookers lined up two deep on the sidewalks, pimps in flashy suits and Cadillacs, and GIs being sweet-talked by girls. The sheriff’s department was on the corner, but the cops appeared to be blind to everything happening around them.

Wilson and his friends went into a bar called the Flamingo Club, where a local named Sam was in the back shooting pool. Sam was dressed in a sharp suit and had diamond rings on his fingers.

"Oh, you that pool-shooting motherfucker I’ve heard about," Sam said. "Well, we’re gonna find out."

Sam bought Wilson a drink, lit up a joint, and started sorting out lines of cocaine. "Go ahead, Pretty Red," Sam said. "Have a toot."

For the next several hours, Wilson, now dubbed "Pretty Red," kept running the table on Sam and two other pimps and taking their money. It was the first time he’d had a drink, much less smoked weed or snorted coke.

"My mind was reeling in everything I saw," Wilson said. "Like a tape recorder pulling in everything, I didn’t understand what I was taking in, but I was taking it in fast."

Sam told Wilson to come by again tomorrow and left to go check on his prostitutes. Wilson went to another bar, where he taught the finer points of billiards to a young lady. The girl asked him to walk her home, and on the way back, she led him into a park and took his virginity.

Back on base the next day, his barracks-mates had newfound respect for him. Ivory Wilson was no longer a hayseed cowboy.

He kept hanging out with pimps, pushing dope and hustling, and sneaking off to see his new girlfriend. It wasn’t long before she told him she was pregnant. Having been raised upright before Texas and the Lord, Wilson proposed to the girl.

When Wilson’s Army buddies caught wind of it, they sat him down for a talk. The girl had been with another soldier they knew who got himself transferred to Germany after she told him she was pregnant.

They gave Wilson a ride to her family’s house, so he could confront her. On the way over, one of his friends slipped Wilson a "windowpane"—a thin slice of gel laced with LSD.

When the car rolled up, and the girl saw Wilson and his friends, she started crying. Standing on her porch, Wilson said he could smell the fresh paint from what was going to be the baby’s room.

She begged him to stay and promised they could make it work, but he stood up and left. Still tripping on acid, Wilson went back to the park bench where he had lost his virginity and cried. At that moment, he said, his heart hardened against women forever.

"Now you got yourself a pimpin’ license, Pretty Red," one of his new downtown friends said.

So Pretty Red skipped town with his new pimp friends and went to Kansas City. He bought five new suits. He was AWOL from the Army for 28 days and came back with nearly $8,000.

When Wilson returned to Junction City he was a minor celebrity, having thumbed his nose at the Army to go cavort with pimps and prostitutes. Naturally, the Military Police threw him in the stockade for 90 days. He was locked up when he turned 18.

"PFC Wilson, you’re a spitshine soldier and a hell of a rifleman, and here you’re going to throw it all away," Wilson recalls his C.O. telling him.

"Fuck the Army," he told them. "I want out."

His commanding officers drafted papers declaring Wilson a Chapter 13—"unfit for duty"—and he signed them on the spot. He didn’t realize it at the time, but he also signed away any future eligibility for VA benefits.

He caught a taxi and threw his old Army clothes out the window as he drove off base.


The next 10 years were a blur of excess, casual violence, and misogyny. He wore diamond rings on his fingers. He owned a Bentley for six months.

"I’m waking up in the morning and having cocaine and Hennessey for breakfast," he said.

He said he pimped in Times Square, before Giuliani cleaned it up. He pimped out of an IHOP at the corner of La Brea and Sunset in Los Angeles. He plied his trade in Fort Polk, Colorado Springs, and Las Vegas, "where I lost all my fucking money."

"In that kind of life, it’s criminal activity, so you move around to where the money’s hitting at," Wilson said. "Convention in town? Bam, I’m there."

Beneath the hats and fancy suits, Pretty Red was still a cowboy. In 1983, he snuck back to Texas to ride in rodeo.

The bull fell on top of him, breaking his collarbone and a few ribs.

Pimps aren’t supposed to enjoy rodeos or George Strait’s "Amarillo by Morning," so Wilson told his associate that some punks in Atlanta had jumped him.


Wilson was charged with murder in 1984 and two counts of conspiracy to distribute cocaine.

The murder charge was dropped. "I was a pimp, not a gangster," Wilson insisted. But he was sentenced to three to ten years in Kansas’s Hutchinson prison for the cocaine charges.

He got on the good side of his boss in prison catering by breaking a colt for his son. While locked up, Wilson wrote A Player's World Manual: Wanna Be a Pimp?

"I heard young men and women using the word ‘pimp,’" Wilson said. "All over news, radio, and TV. Pimp My Ride. Wait a minute! Y’all don’t know what that word means."

So Wilson decided to set down on paper what the world of a pimp was really like. I picked up a copy from Amazon. (Yes, it’s on Amazon.) It’s not exactly Henry James, but it moves with a rough cadence all its own.

"One of the spices of life is jumping in and out of Cadillacs, snorting grade-A coke, and pimping whores," one character in the book declares.

The first half is a narrative of Wilson’s days in Junction City. The second half is a collection of advice on pimping. It is all incredibly vulgar.

"A pimp only fucks whores on Sundays because that’s the only day she has off," Wilson writes. "I was told it was sin to pimp whores on Sundays, so I started giving them Sundays off."

Wilson considers it an honest account of the lifestyle, not a glamorous one.

"If you're happy with your life the way it is now, don't read this book," the preface states. "I wrote this book thinking that I might save a lot of young men from making the mistake I made. In this world that we live, it's man and woman. Once I became a pimp, I had lost the ability to feel or love most things in my life. I'll never get it again."

What struck me as I read it, though, was the similarity between A Player's World Manual and the recordings of our interviews. It occurred to me that Wilson was reciting passages nearly verbatim when I first interviewed him, interspersed with flourishes and asides, like a veteran stand-up or public speaker. When I accidentally erased the first 15 minutes of our interview, we re-recorded it almost word-for-word.


After getting out of jail on out-of-state parole in 1986, Wilson went back to Texas to resume his cowboy ways. Wilson wasn’t quite so young anymore, but the bulls were just as mean.

"The young cowboys were out riding, and that ground hurt!" he said. "Any time you look up and see a set of nuts bigger than your own, you’re in the wrong spot, son. Tell you that for sure."

After one particularly hard fall, his rodeo buddies, whom he had shown his manuscript, suggested to Wilson that he had nothing left to prove. He should go out to the East Coast and get discovered like Calamity Jane, they said.

Wilson moved to D.C. and self-published a run of A Player’s World Manual in 2001. He sold all 300 copies on the street, and even registered a copy with the Library of Congress.

He picked up odd jobs for a while, but soon his money was gone. He struggled with a drug habit, and found himself on the street.

For the past seven years or so, Wilson has stood on the corner of 7th and E in D.C.’s Chinatown, wearing a yellow vest that identifies him as a vendor for Street Sense, a newspaper filled with copy and sold by local homeless residents.

"Maybe I think this is my punishment for using a lot of women," Wilson said in a 2009 profile for the newspaper. "I used so many women I can’t remember names or faces, so I know that it had to be that reason."

Wilson said his attitudes have changed since he sat on that park bench all those years ago. Part of his turnaround may have to do with the fact Wilson has three daughters in different parts of the country.

One of his daughters just graduated from a police academy.


Ivory Wilson 2

Ivory Wilson

Ivory Wilson arrives early in the day on his corner, outside a Starbucks and just down the street from the International Spy Museum, where crowds of tourists and rowdy teenagers stream by.

"Good morning, beautiful!" he says to passing women, many of whom he knows. Wilson may be getting on in years, but he never misses an opportunity to spit a little game.

When Wilson’s done selling newspapers and books for the day, he strolls over to Iron Horse, a biker bar, for a cold beer or two. And then to a nearby homeless shelter, where he sleeps every night.

When I first met Wilson at the Starbucks for an interview, a small group of his friends and fans were there to greet me as well. Wilson is on a first-name basis with just about everyone who frequents the block.

"Ivory is a veritable institution on the corner of 7th and E," Steve Leinwand, who works around the corner, told me over the phone. "He knows everybody: the other homeless people, the lawyers at AARP, the owners of the restaurants."

Robert Church, who also works around the corner from the Starbucks, helps transcribe and design flyers for Wilson’s books.

"He's basically running a business out of a Starbucks and a frozen yogurt place," Church said. "He's got attorneys that work with him to read contracts, and people to help him transcribe and publish his books. He knows how to get his books in the Library of Congress."

Wilson’s mail is delivered to the Street Sense office in the Church of the Epiphany. In a few rooms on the upper floors of the church, the five-person staff and volunteers of Street Sense put together the bi-weekly paper.

Street Sense publishes short stories, poetry and other writing by its homeless vendors in every issue. Executive Director Brian Carome said the benefits of writing and being published are almost incalculable for the vendors.

"It’s far more impactful than the money the paper puts in the vendors’ pockets—the sort of transformative opportunity to understand that your story has power and is engaging," he said.

Wilson credits his many fans with helping him stay clean and giving him motivation.

"The people I see every morning, I get strength through them," Wilson said. "And see that I can be somebody."

Of course, the money helps. A good Street Sense vendor can make better than minimum wage, Carome told me.

And Wilson can move a product. His second book, Big Mack, was just released. It picks up where the first book left off, chronicling how he lost his Bentley and became a Street Sense vendor. He’s already sold 100 copies on the corner.

Wilson is most proud of his soon-to-be-released third book, a collection of short fiction called The Magical Stories of Ivory Wilson.

Wilson has one more book he’s working on, called Weekend Cowboys. It’s about his old rodeo buddies who partied and rode bulls on weekends while holding down jobs the rest of the week.

Wilson isn’t sure if he’ll continue writing after Weekend Cowboys, but he said he is done with the corner. Done with Street Sense. Done with living in a shelter. He’s planning on taking a long bus trip to visit two of his daughters—one in Florida and one in Kansas—before heading back to Beaumont for good.

He’ll be leaving his fans behind.

"He's a very energetic guy, very entertaining, but he's a hustler, always working every angle," Robert Church said. "You can’t argue he’s not trying to do something."

Church said his boss, who studied classics at Loyola and very much does not consider Wilson’s blue material to be part of the Western Canon, put her finger on what makes Wilson special.

"She told me one day, ‘You realize he's still pimping, right? He's got every one of us.’" Church recalled with a laugh.

"And I said, ‘Damn. You're right.'"

Published under: Media