Memoirs of a Dockmaster
Henderson Rose (b.1969)
Pines Harbor Dockmaster,1986 - 1990
I grew up on Fire Island in the late 1970s. My grandfather ran the concessions business in Sailor’s Haven and as a young boy I visited the different communities, including Cherry Grove and the Pines. It was a great way to grow up. My friends and I went boating, surfed, hung out at the beach and ate slices at Cherry Grove Pizza.
On one hand, it was a very safe environment. Gay and straight people mixed together easily, and everyone looked out for each other. On the other, it was somewhat permissive -- thanks to my indulgent, straight uncles I had my first drink at the Ice Palace in Cherry Grove at age 15!
The Ice Palace in Cherry Grove circa 1979. Photo credit: Unknown
In 1986 my brother Scott and I were in search of summer jobs. Our uncles, who were regulars at Blue Whale Tea, introduced us to Rudy, the Harbormaster of the Pines. He hired us as dockmasters. Rudy was a living legend at that time. He simply went by Rudy. No last name was ever used or needed.
Rudy was of German origin and had a strong accent. He was frequently seen around the harbor in an officer’s cap, with a cigarette glued to his lips. A gay man, he lived with his partner, Bud, in the coops.
Rudy with an Invasion reveler circa 1988. Photo courtesy of Henderson Rose.
Rudy took Scott and me under his wing. As dockmasters, our duties were to ensure the safe flow of traffic in and out of the Pines Harbor, allow only authorized boats to use the slips and help people get on and off their vessels safely. This included people who traveled by seaplane, which tied up to a floating dock adjacent to the harbor.
Seaplane at Pines Harbor. Photo courtesy of Henderson Rose
On Sundays, we assisted Sayville Ferry Service in setting up a newspaper stand so residents could get the New York Times or Post. These were the days before internet and getting the paper was very important to many in the community.
Harbor service ran from early morning until 11 pm and the staff worked in shifts. If we didn’t have an early shift our mornings involved surfing before walking to work. A small community, sometimes the Suffolk County Police beach patrol would give us a ride in.
The mornings and evenings were the busy times, and the layout of the harbor made getting around a little difficult. Fridays and Sundays in the summer were particularly intense, with planes coming in almost every 30 minutes and private boats and ferries arriving all the time. This had us running around, communicating via radio and solving problems on the fly.
Henderson Rose circa 1988 in the Pines Harbor. Photo courtesy of Henderson Rose.
On the weekend evenings, as the events at the Pavilion got going, we would work with the Suffolk County police to keep order. House parties were a thing and I remember seeing a lot of scantily clad young men heading to what looked like toga or caveman parties. Most of the time everything flowed smoothly as the Pines crowd was good natured and respectful. However, one day, a dead body floated into the Harbor. The police fished it out and started an investigation. It was a stark reminder that bad things can happen, even in paradise.
Every season there were a number of boaters who rented slips for their vessels.
Pines Harbor circa 1977. It is a post card given by Rudy and Bud to Henderson Rose.
One of my most vivid memories is of a yacht that we called “Lemon Peel”. It was one of the largest and was owned by the nephew of the Shah of Iran. In the late 80s, the Iranian regime had put out a bounty on every one of the Shah’s Relatives around the world, so security was a major concern. When this vessel pulled in Rudy and I would go on board to make sure they had everything they needed. I remember standing there between two guards with Uzis who they told us they would be guarding the boat around the clock. Of course, we notified the Suffolk County police about the situation so they could all work together. Looking back, it was a pretty surreal experience.
The most hectic day was July 4th when there was the Annual Invasion of the Pines. From a dockhand perspective the Invasion is organized chaos. Every boat in the slips is filled with people, and the harbor front buildings and walks are packed to the gills.
Invasion in the Pines Harbor circa 1986. Photo credit: Unknown.
When the invading drag queens arrive the noise is deafening. They come in on a ferry, which tilts heavily to one side as the queens rush to wave to the welcoming crowd. The party is the bomb! Everybody is there -- gay, straight, in-drag or not -- drinking, dancing and having a good time. Inevitably, one or two people get a bit messy, but for the most part everyone is happy and enjoying themselves.
Working in the Pines was a lot of fun. Over time Rudy and Bud became like uncles to Scott and me. They would regale us with tales of the past and the people who had been out in the Pines, including Marlon Brando, James Dean, Marilyn Monroe, Hugh Hefner, Elizabeth Taylor and Truman Capote. As a kid, before I became a dockmaster, I actually helped Elizabeth Taylor out of her boat. Being around Tea Dance at the Blue Whale was always a good time and every summer John Whyte, the owner, would have a fashion show around the harbor pool deck to raise money for the Pines Conservation Society.
Runway at Pines Fashion Show. Photo credit: Unknown.
The other dockhands were really cool people and great to work with. One of them, Tammy Walsh later became even more embedded in the community, marrying landscaper Mike Jaggi and starting a business called Flower Girls. My brother and I also became friends with the kids who worked at the Pantry and Liquor Shop.
We’d hang out, have lunch together, and after work we’d hitch rides on the water taxis to go to the Grove to have dinner and party. We were kids. It was summer and we were on the water. It was loud and raucous with music playing at high volume. You couldn’t have asked for a better time!
Fire Island Water Taxi. Photo credit: Unknown.
One of the great things about the job was I got a meet a lot of celebrities, especially from Broadway and fashion world. These included Joel Grey, Calvin Klein, Colleen Dewhurst, and Geraldo Rivera. I also met Tony Randall several times and he was always extremely nice to us. One of my favorites was Geoffrey Beane, who would arrive in a full suit on a Friday and strip down to tee shirt and shorts immediately after getting off the seaplane. Another was John Laub, the famous painter, who set up his easel in the harbor and capture the beauty of the Pines on canvas. One year, Madonna and her boyfriend Warren Beatty arrived on the seaplane to visit her brother Chris who had a house on Shore Walk. Unfortunately, both of them looked a little seasick when they got off but were both perfectly nice
Another time, Tommy Tune, who had a house on Ocean, introduced me to Twiggy. I didn’t know who she was, but my grandmother gave me a full account when I spoke to her after.
Tommy Tune’s house on Ocean Walk. Photo credit: Unknown.
And it didn’t stop there. I met both Isabella Rossellini and Liza Minnelli. For a young man, this was like living in a movie. I had to pinch myself to make sure I wasn’t dreaming.
Another one of the benefits of being a dockmaster was I sometimes got gigs to help out at some of the parties that took place throughout the summer. These parties weren’t just glamorous, they were over the top. I had never seen anything like it.
One year, Gloria DeMann and her husband Larry had a huge party at their house on the Great South Bay called Reflections. A benefit for God’s Love We Deliver, it was filled with celebrities, including Peter Allen, the Radio City Rockettes, and a number of Chippendale Dancers.
Peter Allen performing at benefit. Photo credit: Unknown.
I was asked to take care of Joan Rivers, who I didn’t know much about beforehand. She turned out to be amazing -- very funny and very kind. She made it clear to me she didn’t drink alone so if she had a drink, I was to have one too. At one point she asked me to go to a bedroom to retrieve a bag for her. Next thing you know, I walk into a room full of Radio City Rockettes in various stages of undress! They paid me no mind and all I could think of was: “If only my friends could see me now!”
Joan Rivers at benefit. Photo credit: Unknown
Later on, the Chippendale dancers asked me to get them more hairspray. Their room was already filled with thick clouds from the many cans already there, so I asked if they really needed more. They turned, looked at me and chorused: “Yes!”
Chppendale dancers at benefit. Photo credit: Unknown
As much fun as I had, during my time as a dockmaster the AIDS epidemic was sweeping through the Pines. It cast a pall over things. I was well informed about the disease and had no hesitation helping those afflicted. Many times, I helped people go to the dock for what was to be their last sunset or arrive on the ferry for goodbye conversations. The love and compassion people showed for their sick friends and lovers touched me deeply. In some ways, it made me feel closer to the community and proud to be a part of it.
When summer was over and I went back to school, some kids tried to tease me about working in a gay community. My response:
“You only wish you could be on Fire Island! You have no idea how amazing it is!”
And then I would tell them stories from the summer and explain to them what a great place Fire Island Pines is. It blew their minds. These conversations also helped me to educate them a bit about AIDS, dispelling myths like it could be transmitted by mosquitos.
After four years working in the harbor, I graduated college and realized I needed to get a ‘real job’. I left the Pines to build a career in healthcare. It was sad, but I resigned myself to the fact that all good things come to an end.
Sunset at Pines beach. Photo credit: Unknown.
What I didn’t realize at the time was the Fire Island Pines would never leave me. Thirty five years later, my memories and feelings about that time are as fresh as ever. I consider myself so fortunate to have had the experiences I did. I learned a lot, especially from people like Rudy, and it helped shape my character. And I got to live a life most people only see on TV or in the movies. Nowadays, my family and I try to get back as often as we can. And every time we do, I am reminded that I had it right as a kid – the Pines is one of the most special places on earth.
