Bootlegger Boston

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

- Mike Hodgkinson

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, block headed 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.

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