New York Pimp: ‘Gentleman of Leisure’ – An Interview with Bob Adelman

New York Pimp: ‘Gentleman of Leisure’ – An Interview with Bob Adelman

When The Rialto Report was approached to advise the production team for the upcoming HBO series, ‘The Deuce’, we recommended a number of books that would provide useful context to the period.

These included Tina Russell’s autobiography ‘Porno Star’ (1973), and ‘Ladies of the Night’ (1973) which described the lives of call girls in New York.

Another book we endorsed was ‘Gentleman of Leisure’ (1972) which documented a year in the life of a New York pimp called Silky and his group of prostitutes, Lois, Linda, Kitty, Tracey, and Sandy. It is a striking collection of fly-on-the-wall black and white photographs and interviews, offering one of the first pictorial glimpses into this world. The candid pictures range from touching Christmas portraits to trips to the tailor.

After seeing the premiere of the pilot of ‘The Deuce’, we were pleased to see many of the street fashions of the pimps and their girls faithfully reproduced in the show in all their gaudy excellence.

The original photographs were taken by Bob Adelman, who photographed cover stories for countless magazines, including Esquire, Time, People, Life, New York, Harper’s Magazine, The New York Times Magazine, and Paris Match. In the 1960s, he had documented notable civil rights events, and his photographs have been exhibited at the Smithsonian, the American Federation of Arts, and are included in the collection of the Museum of Modern Art.

Bob passed away in 2016. Shortly before his passing, The Rialto Report interviewed him about his memories of ‘Gentleman of Leisure’.

The DeuceScene from ‘The Deuce’ – the upcoming HBO series

‘Gentleman of Leisure’ can be purchased from Prometheus Book.


“The term is pimp, but I don’t use it. I’m a professional gentleman of leisure. I have absolutely nothing to do. I stay in bed and take showers. I am a connoisseur of resting and a television freak. If I were in another way of life, I’d have to hustle more. As a black man I’ve never had alternatives anyway. I could have played first base, run the mile, or become an entertainer, but I was a natural pimp, so I just pursued my talents… And I make more money than the President.”

– Silky

Gentleman of LeisureSilky and his family


What got you interested in documenting the life of a pimp?

I had the luxury to pick and choose the projects I wanted to do, and was attracted to dark subjects. I got interested in prostitution because I thought that the human body was the ultimate commodity. You’re literally selling yourself, and I wondered what that was like in a commercial society. There’s a good reason the client is called a ‘trick’… he may be having sex with a prostitute but she isn’t giving away any of her love. He’s being tricked.”

How did you come to execute the project that became ‘Gentleman of Leisure’?

It was simple really. I had my camera and Susan Hall who did the interviews had a tape recorder. The big thing we had was this incredible access. No one else had been allowed into this secret world before. So it was difficult to mess it up.


“White society looks down on pimps. They make life hard for us, but they’ve been doing this to black people for four hundred and thirty-five years, and we’ve witnessed this prejudice, so we must be pretty strong. I’ve survived and I’m successful, but nobody’s helped me. Society doesn’t like success in any black person.”


Gentleman of LeisureSilky goes shopping. Under his arm, he carries material which he purchased to have five suits tailored to his own dream.


What struck you most when you started to document this world?

Well, the fashion hit you straight away. You couldn’t avoid that. These mink coats, ornate chucky jewelry, over-size hats, diamond-encrusted watches. I photographed a tailor who specialized in this fashion. It was an over-the-top fetishization of clothing. Clothes were a preening animalistic expression of power.

He had a car, a gold Eldorado Cadillac, custom-built with an alligator skin roof and a Rolls Royce grille.

Then there was the ‘code’. A complex system of rules that imposed discipline on the girls, but which gave them the feeling that they were living a glamorous existence. I learned how a square girl is ‘turned out’ to be a ho and a pimp’s ‘wife.’ It’s an elaborate process.

And it worked. Silky kept his circle together through thick and thin.


“You can’t force a girl into this situation. The girls are not slaves. My girls decide to share my life themselves. It’s their decision. A girl might leave and I might go get her. But usually I’m real, show her my charming self, and she chooses to stay.”


Gentleman of LeisureSandy receives a present from Silky, and then gives him a wallet and $800


How much control did Silky have over his group of women when you were there?

Oh, it was complete. This was no act. He was their everything. But it wasn’t a one way manipulation or exploitation. There was a real bond between them, and that’s what we tried to show. It’s easy to dismiss that part of their relationship today, because we’re ‘enlightened’ and politically correct. But there was a loyalty and tenderness that existed too.

At the heart of all this was a love story. Maybe not one you’re used to seeing, but a love story nonetheless.


“A girl who is a prostitute becomes good at manipulating men. Because I am aware, I don’t allow her to manipulate me. With me, she has the one relationship that isn’t a ‘use’ relationship. She needs a pimp for her private life. He’s the only one who can understand, appreciate and handle her.”


Gentleman of LeisureSilky and his ‘tools’ – the diamond watch cost $6,000 and the ring $2,000. They are birthday gifts from his ladies.


How manipulative was Silky?

He was a smart guy, no doubt. He had an astute understanding of human nature and especially that of his ladies. He would know instinctively when to calm them, sooth them, or when to arouse their jealousy and anger. He knew their pressure points, and he pressed them. And then he was there to pick up the pieces afterwards.

Did you see things that made you uncomfortable?

Sure. The girls worked very long hours on the streets. There were beatings. Not many but certainly a few.


“If a girl is interested in building a life with me, then I can make an investment in her and give her a foundation. She gets an apartment and presents on her birthday, Christmas, and out anniversary. The relationship builds.

The only way she can be with me is my way. When I feel she’s swept, I make my points. Women are drawn to me sexually, but I purposely try to underplay sex. If the relationship begins with me personally, then I can keep her with my charming personality. We begin to like each other. If she likes me well enough, she’ll do anything.”


Gentleman of LeisureSilky enters his car at Kennedy airport where he has gone to pick up Sandy.


What was it like to be in middle of all this?

It was a real-life soap opera, so you couldn’t help be drawn in. The challenge was trying to stay on the outside and remain at a distant. Not to lose your journalistic principles. The golden rule is never to become part of the story you’re covering.

What did Silky think of the book?

He liked it of course. It was about him! But he was more visible after it came out and that caused him problems.

What kind of problems?

Problems with the law. He became a target because of the book. I’ll just leave it at that.


“Every girl gives me all the money she makes. In turn, I give her a place to stay – her own apartment if she’s been with me for a while, I pay her bail, and she has ten dollars a day expense money.

Pimping is mentally hard. Everything you’re doing is with yourself and for yourself. You have no one to answer to except yourself. I running my own business. I’m the president and the whole corporation.

A girl makes a sacrifice for me. The only greater sacrifice would be for her to jump out of a window. A girl gives up her home, her relationship with her family. I become her whole life. That means our relationship is more passionate and romantic than most.


Gentleman of LeisureKathy cries when she discovers her coat is mink, not rabbit


Is Silky still alive?

Yes, I’m still in touch with him. He’s no longer in New York but he’s still out there. He’s still hustlin’. He’s still looking for an angle, and doesn’t give up anything for free.

What if I asked him for an interview?

You should only do that if you’re willing to be hustled. He’d want to know how it would benefit him. He’d control you in the process. Can you handle that?

I like him though. He’s a unique character. He just does what he does.


“The game is deep. In being a mack, you’re supposedly the supreme being of man. Man rules woman. In being a mack, you acknowledge this fact.”


Gentleman of LeisureSilky is fitted for $900 worth of suits


Gentleman of LeisureSilky makes a toast in front of his gold-painted Christmas tree


Gentleman of LeisureSilky and Sandy drink champagne in a nightclub


Gentleman of Leisure


Gentleman of LeisureLinda leaves Silky and buys a pair of pants and shoes. She then returns to the motel.


Gentleman of LeisureLois and Linda go out to work on Sixth Avenue and 58th St in New York


Gentleman of Leisure


Gentleman of LeisureSilky, Betsy, and Kitty at a game stand


Gentleman of LeisureTracey and her twin sister, who is also a prostitute.


Silky’s friend Dandy and his girls arrive at Silky’s for a party


Gentleman of LeisureSilky and his fellow pimps


Gentleman of LeisureDandy and Silky blow out the candles. They share the same birthday.


Gentleman of LeisureSilky, high on cocaine, smokes marijuana


Gentleman of LeisureLinda and Silky on Georges boat


Gentleman of Leisure


Gentleman of LeisureLinda and Silky go for a ride in George’s boat. The New York skyline is in the background.


Gentleman of LeisureSilky and Linda


Gentleman of LeisureLinda in her apartment. She pays $325 a month rent.


Gentleman of LeisureKitty undresses with a client


Gentleman of LeisureKitty with a client


Gentleman of LeisureKitty with a client


Gentleman of LeisureKitty in her apartment after the client leaves. She makes abut $300 a night when she works hard.


Gentleman of LeisureSilky and Sandy


Gentleman of LeisureSilky preens in the elevator in his apartment building


Gentleman of LeisureSilky and Sandy


Gentleman of LeisureSandy


Gentleman of LeisureSilky



  • Posted On: 18th June 2017
  • By: The Rialto Report
  • Under: Articles · Photos


  1. Bob Dobbs · June 18, 2017 Reply

    Fascinatingly sad glimpse into a subculture I cannot even begin to wrap my head around.

  2. Stevie Geee · June 18, 2017 Reply

    Pretty amazing pictures, and Silky is a character….. you need to do a podcast with him.

  3. Don Tucci · June 18, 2017 Reply

    Silky’s comments are so “of the time”. It’s some how nostalgicly sweet and outrageously sexist at the same time!

    Crazy life.

  4. Anon · June 18, 2017 Reply

    Love this. Where are the women now? Thanks.

  5. Annette Heinz · June 18, 2017 Reply

    He seems to be one of the nicer pimps. The women need him, emotionally, to feel loved.

  6. Jim Stevens · June 18, 2017 Reply

    At first glance in the group shot of the girls, the one on the top left (Kitty apparently) looks distractingly like “Pamela Mann” star Barbara Bourbon. The later shots made it obvious it’s not her, but that threw me for a minute. And not in a good way.

  7. Charles Tatum · June 18, 2017 Reply

    Yup, it would be fascinating to see what happened to the women!

  8. Steph Johnson · June 18, 2017 Reply

    I knew him personally. All the pimps hung out in the Wagon Wheel and the Peppermint Lounge. hey would all have custom made clothes, lots of gold jewelry and alligator shoes. There was a store called Layton’s that sold all those shoes at about $1200 a pair. any of the pimps would try to talk me up. There dress cod and cars and too much jewelry were funny to me. Silky would tell them to leave me alone. He had many ladies that worked for him. They all kn\\\\\dirty pimer. They were called Wife In Laws . It amazed me why some lady would turn tricks and turn over all her money to a guy. My best friend worked for another Pimp. She had to make $1000 a night. Because these guys had up to 10 ladies, the lady would be lucky if she saw her Pimp every 2 weeks. Vicki could not even buy herself anything without permission from her Pimp!!!!! There was this Pimp called Frankie Palmer who was not even good looking. He had about 13 ladies. Many of the Pimps came from Cleveland. One Pimp had a lady that looked exactly like me. One time I hailed a cab and told him my destination. He took me to 50th St and Lex. I said this is not what I said. He said this is the corner you work. I said what!!!!! Another time this Pimp approached me and asked where is my money? It was the pimp of my look a like. When I finally say this lady, she looked like my twin. When crack came on the scene, many of the Pimps got hooked. Years ago I saw Frankie Palmer looking in garbage pails for trash. He was dirty and nasty, but still had on his old pimp hat. I found out he was a Mole person, They are the homeless people who live underground in the shut down NYC tunnels. Also there were 2 twins that were big pimps in the day. I saw one begging for money on the street. My friend Vicki whose Pimp was Dutch found out he was married to this ugly woman and had a great home in upstate. After many years of working for him, she quite the business and only dated women.

    • Adrian · June 21, 2017 Reply

      Steph, sounds like you have many great stories to tell! Great post!

    • A. G. Frumanuther · September 17, 2017 Reply

      You sound like a renegade, to be real. But I definitely enjoyed reading your comments all the same – there was a ring to truth in them, even if not being honest about your own involvement in “The Life”
      I bought this book after reading half of it in a B/N – was worth the money, the story was so true

    • Dave · October 14, 2020 Reply

      I remember those days. Did you know Calvin Ferguson? The one called ”Sweet Jesus? How about the guy who’s car they used in the movie Super Fly,K.C?

    • DomesticDive · November 3, 2023 Reply

      Did you know that he recently passed away? Within the last week in Cleveland, OH.

  9. mondo_kane · June 20, 2017 Reply

    The women are probably all dead. Or most of them, anyway. Prostitutes don’t exactly have long life spans.

    The fact is he gets most of the money, while they get just enough to live on and buy some clothes every once in awhile. And that’s the ones who are treated better than most. Not exactly a business or lifestyle that should be glorified.

    Still, this is an interesting pictorial of 1972 New York.

  10. Darren · June 24, 2017 Reply

    Strange, weird, and disconcerting insight into a hidden world. Quite how the photographer managed to get the permission to penetrate this secretive world must be a story in itself.

    I too would love to hear from the women in the family. What are their thoughts on this era now?

  11. Eeeee · June 24, 2017 Reply

    This piece is a prime example of why I love the Rialto Report. It doesn’t have the narrow view of relevancy that most (all?) others do in this field. By doing this the context comes alive in a much more vivid fashion. Good job.

  12. Cathy Gigante-Brown · July 3, 2017 Reply

    I found this fascinating, thanks! It really captured the age and time.

  13. MMAMeetsBoxing · September 2, 2017 Reply

    Thank you so much for sharing this article. Will you interview Silky??

  14. Jack Presentine · February 6, 2021 Reply

    Masterpiece, finally some real insight.
    I rank it up there with Iceberg Slim

  15. Kenny · April 27, 2023 Reply

    I remember reading this book in 1975, everybody aspired to be a pimp, a player, or the Mack daddy… most of them ended up in prison…

  16. DomesticDive · November 3, 2023 Reply

    It is my understanding that “Silky” recently passed away in Cleveland, OH. Within the last week as of this writing.

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