Anatomy of a restaurateur: Don Dickerman

dickermanrev Don Dickerman was obsessed with pirates. He took every opportunity to portray himself as one, beginning with a high school pirate band. As an art student in the teens he dressed in pirate garb for Greenwich Village costume balls. Throughout his life he collected antique pirate maps, cutlasses, blunderbuses, and cannon. His Greenwich Village nightclub restaurant, The Pirates’ Den, where colorfully outfitted servers staged mock battles for guests, became nationally known and made him a minor celebrity.


It might seem that Don’s buccaneering interests were commercially motivated except that he often dressed as a pirate in private life, owned a Long Island house associated with pirate lore, formed a treasure-hunting club, and spent a small fortune collecting pirate relics. He was a staff artist on naturalist William Beebe’s West Indies expedition in 1925, and in 1940 had a small part in Errol Flynn’s pirate movie The Sea Hawk.

piratesdenmenu225Over time he ran five clubs and restaurants in New York City. After failing to make a living as a toy designer and children’s book illustrator, he opened a tea room in the Village primarily as a place to display his hand-painted toys. It became popular, expanded, and around 1917 he transformed it into a make-believe pirates’ lair where guests entered through a dark, moldy basement. Its fame began to grow, particularly after 1921 when Douglas Fairbanks recreated its atmospheric interior for his movie The Nut. He also ran the Blue Horse (pictured), the Heigh-Ho (where Rudy Vallee got his start), Daffydill (financed by Vallee), and the County Fair.

bluehorsephoto226On a Blue Horse menu of the 1920s Don’s mother is listed as manager. Among the dishes featured at this jazz club restaurant were Golden Buck, Chicken a la King, Tomato Wiggle, and Tomato Caprice. Drinks (non-alcoholic) included Pink Goat’s Delight and Blue Horse’s Neck. Ice cream specials also bore whimsical names such as Green Goose Island and Mr. Bogg’s Castle. At The Pirates’ Den a beefsteak dinner cost a hefty $1.25. Also on the menu were chicken salad, sandwiches, hot dogs, and an ice cream concoction called Bozo’s Delight. A critic in 1921 concluded that, based on the sky-high menu tariffs and the “punk food,” customers there really were at the mercy of genuine pirates.

As the Depression deepened business evaporated, leading Don to declare bankruptcy in 1932. A few years later he turned up in Miami, running a new Pirates’ Den, and next in Washington D.C. where he opened another Pirates’ Den on K Street in Georgetown in 1939. In 1940 he opened yet another Pirates’ Den, at 335 N. La Brea in Los Angeles, which was co-owned by Rudy Vallee, Bob Hope, and Bing Crosby among others. In the photograph, Don is shown at the Los Angeles Pirates’ Den with wife #5 (photo courtesy of Don’s granddaughter Kathleen P.).

© Jan Whitaker, 2008

Learn more about Don Dickerman’s life.


Filed under Offbeat places, proprietors & careers

25 responses to “Anatomy of a restaurateur: Don Dickerman

  1. Hi nice reading your blog

  2. Julie Daniels

    Hi there, my grandfather was great friends with Don Dickerman and was also one of the artists on the Arcturus with Dickerman and Beebe. I have some photos of Don posing (as a pirate… Go figure… Haha) for one of my grandfather’s wax miniatures he did. My grandfather’s name was Dwight Franklin… If you are interested in the pictures or copies, I would be happy to share! My grandfather was equally a fascinating character with his work (mostly dioramas) featured in many museums one of his figures even made it to Teddy Roosevelt’s desk, and also the go to guy in old Hollywood as an advisor for pirate costume, military arms and uniforms and civil war stuff. I enjoyed your article. Feel free to contact me!

  3. Pingback: 1916: Crazy Cat and the Bohemian Greenwich Village Felines of Sheridan Square, Part I | The Hatching Cat

  4. I just came across a menu and a postcard from the Pirates Den Hollywood. Really cool pieces. If anyone on here is interested in them, please let me know via email at and I will be happy to send pictures. I will be posting them for sale very soon so act quickly.

  5. My grandfather Charles Valentine “Tiny” Huddelson worked at the Pirates Den in DC on K Street.

    • Janet

      Karen, would you know whether or not my grandfather, Roy Armstrong, worked with your grandfather, Tiny? Roy was known as “Pickle Puss”. I do have a photo from a Miami newspaper at my home with a group of people at the Pirate’s Den. I’ll have to look up “Tiny”. From what I have gathered, Roy moved around and was at a number of different Pirate’s Dens, Miami, NY and DC.

      • Hello everyone! My company is working on a documentary about the Bayou which was a nightclub located in the same locale as the Pirate’s Den when the building changed hands in 1953. We are interested in any Pirate’s Den photographs, memorabilia that you may have from the Washington, D.C. location and are happy to share with the project.

        My office number is 301-608-9077, and my cell is 301-370-5898. Email is


  6. Vickie Nelson Eliot

    My father, Peter Burroughs, Newport Beach, CA. was a life long friend of “Uncle Don”. We often ate at Don’s restuarant in Newport, “The Castaways” in the 1950’s. Uncle Don asked that I keep his “Red Geranium Club” going. Do you know anything about this club? I have pictures, momentos from “Uncle Don” and am willing to share them.

    • Jim Dukette

      I’m researching Cap’t. Don, Castaways’ Club on the bluff in Newport Beach, and Balboa Pirate Days. If you have pictures and stories I’m willing to look and listen.

  7. Dorothy Mowatt

    In reply to Janet…I suppose anything is possible as to “rum running” but the way I understand it, and I still wonder about it, is that even in the nightclubs he owned in New York during prohibition, there was no alcohol served??? I do remember hearing the name “Pickle
    Puss Armstrong”. There may be pictures with him in my collection but he may not be named…I also have pictures taken years ago at his camp in Lovell, Maine playing boat polo. The Lovell Historical also sent me a collection on a CD’s given to them by Don….If she can send her email address to perhaps I can send some to her…This is getting interesting…what are the chances two granddaughters of this unique group end up blogging about the Pirates Den???

  8. Janet — Fascinating questions! They go way beyond my scope of research. I know of no employee records. Dickerman was an avid collector of pirate items, but I can’t say I found any hint of illegal activities on his part. (Of course it is true that much of the dark side never makes it into the press.) I think we’re in “deep throat” territory now. Anyone? — Jan

  9. janet

    My grandfather, Roy Armstrong, worked for Don Dickerman at the Pirate’s Den…. in Long Island, then in Miami and maybe even in Washington. Is there any way of finding out when he might have worked at these different places? I have several newspaper articles, but no dates. One from Miami refers to them playing boat polo, and my grandfather is referred to as Pickle Puss Armstrong. Could he have been a rum runner from Cuba? Did Dickerman have people running rum for him? My father was born and raised in Miami; a job in high school was to sweep up broken glass at the Pirate’s Den in Miami. That would have been some time in the 30’s? Did Dickerman ever live in Tampa? The only picture I saw of my grandfather when I was little was of him dressed as a pirate. I thought it was real. Any information out there? Janet

  10. Dorothy Mowatt

    Jan, I just went through the website and am amazed at the amount of restaurant history you have researched. I sent a previous email tonight and then got to wondering, after checking around the site, where you had gotten the information on Don Dickerman. As I mentioned before he was my grandfather and was delighted to see the piece on him…Nice job…Dottie Mowatt

  11. Dorothy Mowatt

    Tonight my son emailed me about the article of Dec.8, 2008 on Don Dickerman…Don was my grandfather. I couldn’t believe it when I saw the article..A Richard Thornton from Scotland commented that he had an old Matchbook from the Pirates Den and he was going to list it on ebay. I must have missed it because I couldn’t find it. Did he leave an email address I might be able to contact him and see if it is still available? Thank you for any help you might give me. Dorothy Mowatt

    • john armstrong

      My dad Roy Armstrong was Don Dickerman’s master at arms at his clubs and my two older brothers used to clean up the place on the weekends.

    • Julie Daniels

      Dorothy, my grandfather was friends with Don and was in the Arcturus with him, I have my grandfather’s journal of the trip and remember him telling me what a great man he was… I have pics of my grandfather with your grandfather posing for one of my grand’s wax figures. And probably lots more… They remained life long friends.. Feel free to contact me!

  12. Richard Thornton

    Hi there, I have an old 40 strike Matchbook from Don Dickerman’s Pirate Den that mentions the Council of Pirate Chiefs. Rudy Valee, Errol Flynn, Bing Crosby, Bob Hope, Johnny Weissmuller & other members. It is full of information regarding the Pirates Den. I was pleased to find a site dedicated to him. I am going to be listing it on this week (12th Feb 2009) I have around 7,000 USA Matchbooks & enjoy Americas history. I am from Scotland in the UK.
    Thank you,
    Richard Thornton.

  13. Hi Louise. According to a 1929 syndicated column, “He says his home at Port Washington, L.I., was built by a pirate-fighting Colonel Baxter in 1673.”

    Changing the subject a bit — Something I didn’t manage to fit into my post is that he drew all the artwork for his menus and advertisements.

  14. Great post, Jan. I’m curious as to where he owned a house on Long Island. I’m thinking the north shore but I suppose it could have been out east on the east end. Perhaps, Montauk? I’ve often heard the stories of Captain Kidd burying treasure on Gardiner’s Island…

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