Bootleggers, Trawlers, and a Deadly Chase off Bay Shore – 1926’s Real-Life “Waterfront” Drama

Bootleggers, Trawlers, and a Deadly Chase off Bay Shore – 1926’s Real-Life “Waterfront” Drama

Fans of the hit show Waterfront—which dramatizes how modern-day smugglers use fishing vessels to transport illegal drugs—might be surprised to learn this tactic isn’t new. Nearly a century ago, real-life bootleggers off Bay Shore, Long Island, were doing the very same thing—using fishing trawlers not for cod, but for contraband liquor.

On the night of Wednesday, September 8, 1926, federal dry agents launched a covert mission from a humble rowboat off Bay Shore. Their target? Two fishing trawlers suspected of smuggling liquor during Prohibition—a dangerous game known locally as "fishing for liquid gold."

Shots rang out as the agents approached the trawler Edward Westerbeak, but the officers managed to board. In the chaos, two crew members leapt overboard into the dark Atlantic waters. One of them, William “Big Bill” Apsch, a well-known Bayshore fisherman from Smith St. and Russian immigrant and one of the South Shore’s most successful rum runners, was later found washed ashore. He left a wife and two young children. His partner vanished without a trace, believed to have drowned trying to reach land.

Onboard the Westerbeak were 800 cases of champagne, whiskey, and wine. Nearby, another trawler—Maude S. II—was also seized with 650 cases of liquor and three local baymen taken into custody: George Murdock, William Murdock, and William Allcock.

The federal agents had received an anonymous tip that led them to Bayshore by car. Disguised as ordinary fishermen, they quietly rented a rowboat and paddled out into the dark waters to intercept the bootleg fleet.

Both vessels were eventually towed to Manhattan's Barge Office, their illicit cargo adding to the mounting federal evidence against local rum-running operations.

While the tale ended in tragedy for "Big Bill" Apech, his story is a vivid reminder that the use of the sea for smuggling has a long and deadly history. In many ways, it mirrors what we see dramatized today on shows like Waterfront—the difference being, in 1926, the cargo was liquor, not narcotics.