Bootlegger Boston: Head Back to the Prohibition Era with Emily Sweeney

Local author Emily Sweeney digs up the cops and kingpins of the Prohibition era.

The streets of contemporary Boston map out an intricate network of gastropubs, artisanal fusion restaurants, craft breweries and avant-garde wine bars. Nearly a century ago, that cartography of food and booze was no less complex, but the atmosphere was very different. After nearly a decade of Prohibition—which began in 1920 when the Volstead Act took effect—Boston’s hooch coverage had mushroomed from 1000 licensed bars to 4000 illegal speakeasies. The city even picked up a nick-name: Bawdy Boston.

Some, of course, wore this stain on the city’s good name as a badge of honor. As local writer Emily Sweeney documents in much of her excellent new book, “Gangland Boston,” the bootleggers of Prohibition-era Boston were often in the news. They made a tidy living, hauling in an estimated $60 million a year by 1929. If it wasn’t exactly difficult to find a drink if you knew who to ask—and everyone knew exactly who to ask—it was even easier to find trouble when naked greed, blockheaded recklessness or territorial bravado threatened the underground status quo.

Here, Sweeney picks out a handful of the less savory incidents that arose from Prohibition and its immediate aftermath, so that you can organize a self-guided tour of Bootlegger Boston.

317 Hanover Street in the North End

The North End

“317 Hanover Street in Boston’s North End was once a stronghold for the Italian mafia and the base of operations for Joseph “J.L.” Lombardo, a well-respected figure in Boston’s underworld,” says Sweeney. “It was here that a showdown between Italian mobsters and Irish gangsters took place on December 22, 1931. That was the day that Frankie Wallace, the leader of South Boston’s Gustin Gang, and his two associates, “Dodo” Walsh and Timothy Coffey, showed up at Lombardo’s office and got ambushed by mafia gunmen. Wallace and Walsh never made it out alive. The building where this happened is still right there on Hanover Street: Citizens Bank occupies the ground floor, and there are condo units on the floors above.”

The West End

“A fancy speakeasy was located on the second floor at 153 Causeway Street, across the street from the Boston Garden, on the block between Haverhill Street and Beverly Street," reveals Sweeney. "It was called the Club Garden, and had a peep hole at the entrance and a guard stationed at the door. But those precautions weren’t enough to stop the place from being raided by federal Prohibition agents. On the afternoon of Feb. 11, 1932, two undercover agents talked their way inside the speakeasy, bellied up to the bar, and ordered two shots of rye whiskey. Everything seemed normal until one of the agents suddenly hopped over the bar, grabbed a bartender, and revealed the real reason why they were there. The agent instructed the customers at the bar to stay still and warned that his colleague would “kill anyone who made a move.” And that marked the end of the Club Garden. The feds seized all of the liquor, five men were arrested and the bar was dismantled.”

The Causeway Street speakeasy bust


“In the early morning hours of January 24, 1933, Charles “King” Solomon was at the Cotton Club, an after-hours joint on Tremont Street in Roxbury," says Sweeney. "He rose from his seat and walked into the men’s room. The sound of gunshots suddenly echoed off the walls. Solomon reportedly staggered out from the bathroom, clutching his wounds, and muttered, "Those dirty rats got me.” At the time of his murder, Solomon was 46 years old and under indictment for allegedly running a multi-million dollar liquor smuggling syndicate. Today the building that once housed the Cotton Club now bears the address 888 Tremont Street, and it’s been transformed into loft-style apartments.”

South Boston

“The Gustin Gang was known to hang out at 2 Vinton Street in South Boston," says Sweeney. "On the evening of January 15, 1933, Boston police officer Daniel J. McDonald showed up there in plainclothes and drank some whiskey in the company of the Gustin Gang until he suddenly passed out. One of the men there that night, Thomas G. “Red” Curran, would later turn government witness and testify that Gustin Gang leader Stevie Wallace had spiked McDonald’s drink. Curran told authorities that the gang threw the unconscious officer down the flight of stairs, kicked him out onto the street, beat him, and then left him in a nearby field. Soon after he started cooperating with authorities, Curran disappeared. In May 1933, Curran’s bullet-riddled body was located in an old quarry in West Quincy.”

Bay Village

“David “Beano” Breen was a racketeer from the Bay Village section of Boston," says Sweeney. "He lived on Melrose Street and owned a building at 358 Tremont Street that was home to a popular speakeasy during Prohibition. On December 17, 1937 Beano Breen was fatally shot in the lobby of the Hotel Metropolitan, which was located at 315 Tremont Street. The hotel where Breen was shot was demolished years ago, and is now the site of Elliot Norton Park. Breen’s murder remains unsolved.”

Gangland Boston


Mike Hodgkinson
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