Rum-Running: The First Big Master of the Universe Industry on Eastern Long Island

In 1960, when I started the first edition of Dan’s Papers, I sometimes talked with fishing boat captains in Montauk who 30 years earlier had been involved in rum-running during Prohibition.

From 1920 until repeal in 1933, Montauk, isolated way out on the tip of Long Island and yet so close to New York City, was a major port of entry in the United States for rum-running. Ships from Canada, England or Cuba filled with boxes of hard liquor would anchor just beyond the 12 mile limit. The fishermen in their boats, hired by the bootleggers from New York who came out in their fancy cars, brought the hooch in for them. The pay was $50 a trip.

In those years, the fishermen berthed their dozen or so fishing boats by the railroad dock at the little shanty town on Fort Pond Bay. They had very little money until Prohibition. After that, it was a whole different matter. As one of them told me in 1960 when I soke to him, “we fished during the day and ran rum at night. We never slept.”

By 1960, these former rumrunners, in their 20s back in the day, were 60 or 65 and now well-respected fishing boat captains taking customers out for porgies and fluke, blues and stripers and even swordfish. I’d be down at the docks, not on Fort Pond Bay anymore, because that village had been swept away in the hurricane of 1938, but up in Montauk Harbor two miles away, where hundreds of boats now were docked in a sheltered inlet. And I’d be out there with a copy of this newspaper and an ad rate sheet under my arm, trying to sell ads. Sometimes I’d take a break from that though, and, sitting at the bar at Salivar’s, the main watering hole at that time, I’d ask the fishermen to tell me rum-running tales.

I can’t remember which stories came from who. But some of those I listened to were Captain Clancy Pitts, Captain Carl Forsberg and some of the descendants of Canadian fishermen from Nova Scotia who settled the Montauk Fishing Village some years earlier.

There was the gunfight out at Deep Hollow Ranch out toward the lighthouse.

“The Dickinson family ran the ranch back then. They were just normal people, but they were happy to store hundreds of boxes of hooch in their basement and outbuildings for the bootleggers. That day, two gangs were fighting over the stuff. The Dickinsons laid low. But when several of the men were hit by gunfire, everybody fled. Next the police came. They found one killed. Also $100,000 in cash. That was in all the papers.”


“We had this one old captain, I really don’t want to say his name, he was drunk half the time, but he did his job and very well. Once I was down at the railroad dock and saw him come in. He was coming in much too fast, he just slid up the beach, the boat coming to a stop with a jerk, and it just sent him skipping over the boxes from the stern of the boat to the bow and onto the beach and up into the empty van waiting there where I heard him sprawl with a thump. First thing loaded. First thing unloaded.”


“I was supposed to meet a ship from St. Pierre, Canada by the name of Lawrence McKade so I set out for Block Island where the rendezvous was. Well, damned if I could find the Lawrence McKade anywhere and so after riding around all night and getting low on fuel, I pulled into Block Island Harbor, where I ran into a whole fleet of other fishing boats.

“‘Captain,’ someone tells me, ‘you are too late for the Lawence McKade which has already unloaded and headed back to St. Pierre, but you might help unload the Eye Star which is not far off.

“I drove out to the Eye Star and sure enough he’s got a whole load he’s anxious to be rid of. So he fills me up with a load, gives me a full tank of gas and a cigar box, which is taped shut.

“Hand this to the landing agent at Montauk,’ he says, so I put it down by the wheel where I won’t forget it.

“With this full load I am on my way to Montauk when a warning comes over the radio that the Coast Guard is going to pick me up when I get in. Of course, I can’t have this, so I turn around and head for Rhode Island. The shore is very unfamiliar, so I anchor my boat offshore at this bathing beach where these people are, and swim in to scout around.

“If this isn’t a lucky break because sure enough, I run into a fellow on the beach who works for the New EnglandOyster‘ importer John Smythe. He recognizes my problem and inside an hour he’s with me in the boat and takes me to Smythe’s, where I unload and get a good fair price for everything.

“It’s the middle of the night now and I don’t have any place to sleep or any cases, so I do what anyone in trouble would do and call the Coast Guard at Newport, and they give me a room and bath and a soft bed for the night.

“Well, here it is I’ve been away from Montauk for nearly two days and sure as hell the Montauk Coast Guard knows there is something up, so before I go to bed that night I radio in that I’ll be riding in at 5 a.m. so I’m sure the Coast Guard will be laying for me.

“Naturally, I sneak in at 4 a.m. and there’s no trouble, and when I dock I’m pretty careful too clean the boat so that there is no evidence of anything.

“Come dawn and I’m back down to my boat, and sure enough the Coast Guard has gone over everything stem to stern. That’s when I notice the cigar box I forgot all about, but thank the lord the Coast Guard never looked in that box. When the Montauk Agent opened it up later that day, I see it has $50,000 in $100 bills inside.”

One of the men told me about the Apache. Some very special boats got built for rum- running during the 13 years it was in effect. This one was made in Greenport. The Apache was 55 feet long, made of steel beams and wood, and with no part of it above the waterline except a steel framed bulletproof glass hatch that could be slid open backwards along the deck.

“If a man stood up inside, he could see out,” the fisherman told me. “Of course, that’s also where the boxes went in.”

The ship was powered by two powerful Allison airplane engines. It could outrun any Coast Guard boat. Once, he’d been told, it made a big circle around three of them chasing it, making a smoke screen in the shape of a circle as it went around.

They never did catch the Apache. But in the end, Apache came to them. One night, in a fog, the Apache tied up to what it thought was a freighter from Halifax. And it was all over. It was, instead, a big Coast Guard cutter. So that was that.

The Coast Guard couldn’t arrest the crew because the hold was empty, but instead seized the ship, took out the two engines and then auctioned it off in Riverhead. So the rumrunner bought it back, and was out again rum-running in three weeks.

“One night, I’m sitting on a rock looking out and this rumrunner comes right in close along the arc of the bay, with the Coast Guard in full pursuit, firing shots just behind. They’re gaining. The mate though is really busy, pushing the crates one after another over the side, and with each splash it picks up a little speed, and finally it gets up enough speed to just get away. What I’m doing, of course, is noting the spots where those boxes went in.

“The next morning, I’m out in my rowboat with my son, and we’ve got a rope and a hook and a net over the side trying to find these boxes, and I look up and on the shore is this man I don’t know with a rifle and he says, no thank you, no thank you, just move along, and so we do. You never knew who was your friend and who wasn’t in those days.”

The fishermen told me about the various modes of transportation that got the goods back and forth to New York City. There were trucks, hearses, busses, cars. Many had false bottoms or false compartments.

“I remember this one horse came into town over and over. He’d come out here in a van looking out the back. They’d lead him out of the van and we’d put the boxes in behind him and cover them with hay, then lead the horse back in and back to the city he would go. He’d see the same scenery over and over.”

I was told sometimes the bootleggers would just take a chance—fill a whole panel truck with the stuff and haul it into the city with a sign on the side saying Brooklyn Furniture Company.

“One of them turned over on its side at the top of the hill where Gurney’s Inn is today. The road wasn’t paved then. Everything inside shattered, and boy was that a mess to clean up. We found pieces of glass up there for years and years after that.”

Then there was the story about E. B. Tuthill. Tuthill owned the fish packing house at the Montauk Fishing Village in the early days (it is today Duryea’s Fish House), and he was very disappointed when first told of Prohibition.

But then a friend told him how to make whiskey from beach plums. Put sugar and beach plums into a barrel with spices and water, dig a hole seven feet deep and bury it. Leave it buried a year. Then dig it up. Tuthill did exactly as he was told. One year later, he told some railroad workers next door if they’d like a drink then get some shovels. With great enthusiasm, the men dug and dug, then as the dirt fell away from the barrel, it exploded. KA-WHAMMO. He’d forgotten to put a bung in the barrel when he’d buried it. There was nothing to drink, but lots to lick off your clothes.

There were many other rumrunning stories told to me by the captains out at Montauk Harbor in those early days of this newspaper.And then there were some other wonderful stories I learned about, both in Montauk and the rest of the Hamptons.

In the summer of 1927, two East Hampton residents, returning drunk from a party in Greenport in their Model T Ford at 2 am, failed to make the turn at the town green and just went straight for the pond.

The car stopped after awhile. The engine went silent. In the dark, they could hear water lapping at their car and the sound of crickets.

“I do believe,” the passenger said, peering down out the window, “we have driven into the pond.”

“I believe we have,” the driver said.

The passenger opened his door. Water rushed in, but the door was open enough for him to get out. “You stay here. I’ll get help,” he said. Then he waded off in four feet of water.

By the time he got to shore, however, he’d forgotten what he was supposed to do. So he walked home. Next morning, children walking to school noticed there was a car sitting in the pond. Behind the wheel was a man, fast asleep.

Mr. Rowe, the town pharmacist, was a church-going man. He and his wife lived on Coopers Lane in East Hampton. One morning, after breakfast, Mr. Rowe went out to his garage to get his car, opened the door and found several hundred cases of Johnny Walker Scotch blocking the way to his car. There was no way to get around them.

He went back into the house. “I think I will walk to work,” he told his wife. And he did. The next morning, the boxes were still there, but the morning after that, they were gone. Then he could get his car.

The Volstead Act, which had enforced Prohibition, was repealed in 1933, and so rum-running came to an end. But you can read more stories in the book Montauk An Anecdotal History by Peg Winski, or in the book Ship Ashore by Jeanette Rattray.

A common story in Montauk centers on a gambling casino “The Island Club” on Star Island in Montauk and all the famous people who went there, including New York City mayor Jimmy Walker, who, on August 23, 1930, famously, avoided being arrested in a raid on the premises by folding a towel over his arm and pretending to be a waiter as the feds came in. After the feds left, he successfully fled the building for the safety of the tee-totalling Montauk Yacht Club next door.

In Ship Ashore you will read about the schooner Madonna V, which ran aground in Napeague filled with bootleg liquor on December 23, 1922.

“Lifelong teetotalers and even Deacons of the Church risked pneumonia in the December surf to bring it ashore, prompted no doubt by the inherited custom of ‘wrecking’ and old New England principles against waste of any kind” Rattray wrote.

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