Greater Boston Had 4,000 Speakeasies by 1928

Prohibition did not close Boston's bars. It moved them upstairs, into basements and behind the doors of offices that sold wool or real estate. The numbers from the period are the most Boston thing about the whole era: lots of laws, plenty of enforcement, and a drink in your hand anyway.

Before Prohibition

Massachusetts had been here before. WBZ notes that in 1838 the state passed a temperance law banning liquor sales in quantities under 15 gallons, and repealed it within two years. The later push came from groups that blamed alcohol for wrecking families and marriages, including the Anti-Saloon League. The result was a national ban, backed by religious leaders, politicians and women's groups.

None of this was a surprise to anyone who drank. The legal supply was cut off and, as WBZ puts it, the demand remained.

The count

The city did try to enforce the law. According to the New England Historical Society, the police vice squad made about 25,000 raids and 17,000 arrests in nine years. The same history says it did not get any harder to find a drink.

The society's count of the trade is hard to shake. By 1928 the Greater Boston area counted 4,000 speakeasies, four of them on the central police station's own block. It adds that fifteen thousand people sold liquor, 5,000 of them full-time bootleggers. Those are historians' tallies of an illegal business, so treat them as the scale of the thing, not a ledger.

Walter Liggett, a journalist who spent a month in Boston for a January 1930 magazine piece, called bootlegging the largest and best-paying racket in the city. He wrote that most speakeasies were camouflaged as brokers' offices and real-estate firms.

The rooms

We have names for a few. Emily Sweeney, a Globe journalist who writes about the city's organized crime, is the source for most of them. One speakeasy, the Lighted Lamp, was in a basement at Myrtle and Grove streets on Beacon Hill. In January 1921 police broke the doors down with sledgehammers. Inside they found more than 50 young people partying. Several flappers left in a police patrol wagon. Over on Causeway Street, the Club Garden epitomized the clandestine speakeasies of the West End.

Then there is the Cocoanut Grove. The same account says Charles "King" Solomon's empire featured establishments like the Cocoanut Grove nightclub. We mention it because it is where the glamour and the crime met.

The cop

The best-documented figure is a policeman. Oliver Garrett ran the vice squad, and the Globe once declared that no man was more feared by bootleggers. He was demoted to patrolman in 1928. Liggett tagged him the Million-Dollar Cop. He pointed out that, on a $40 weekly wage, he somehow owned a farm, a racing stable and three cars.

In May 1930 he was indicted on extortion charges. He pleaded guilty and drew two years at Deer Island. That is the part to remember when someone tells you the Prohibition era was fun. It was also a machine for making corrupt policemen rich.

The gangs were a second machine. In South Boston, Frank Wallace and his brothers formed the Gustin Gang. The gang dominated Boston's underworld through the 1920s, per WBZ. The brothers were rarely convicted, thanks to their political connections. Frank Wallace was shot dead in an ambush a few days before Christmas in 1931.

One trace of the gang survives on the map. WBZ reports that the Wallaces were rumored to deliver often to a speakeasy on Old Colony Avenue called The Sportlight, tied to an older Wallace brother. The same piece says the building went on to be Kelley's Cork N Bull and is now Stadium. That is a South Boston bar where the address has outlasted the gangster story, which is more than most can say.

After repeal

The 21st Amendment ended Prohibition in 1933. As one local summary puts it, repeal came with a shift in public sentiment after the unintended consequences, among them organized crime. The Fairmont Copley Plaza's bar, which opened as the Copley Café and became the Merry-Go-Round Bar in 1934, is a small example. It is now OAK Long Bar + Kitchen, and it is the closest thing in our list to a drink with a repeal date on it.

The rooms that trade on it today

We are cautious here, because a lot of "speakeasy" talk is décor. A travel site lists speakeasy-style bars in Boston, and a few have Prohibition in the name. Carrie Nation Cocktail Club is named after the fierce Prohibition advocate, which is a joke at the temperance movement's expense. Offsuit and Yvonne's are on that list, and the list describes Offsuit as an intimate escape hidden in the Leather District. These are modern bars dressed for the era. They are not the real thing, and none of the sources we can open claim otherwise.

The older rooms are a different story. J.J. Foley's Cafe in the South End opened its doors in 1909. The Bell in Hand claims a bar dating to 1795. Whether they poured through Prohibition, we could not find a source that says, so we will not guess. Ask a bartender.

What to do with this

If you want the history in a glass, skip the fake bookcase and drink somewhere that was pouring before your grandparents were born. An old bar beats a password every time. If you want the costume, pick one of the speakeasy-style bars and enjoy it for what it is. The city also tried to zone vice out of sight later in the century; that story is the Combat Zone. Check what time they close, because why Boston closes so early explains the rule that decides when your night ends. The liquor license cap explains why many of these rooms are in the same few neighborhoods.

And get home safely. The Last Train page shows the last departures from your station, and getting home after last call covers late buses and fallbacks.

Where to find a serious drink today is in the cocktail bars worth the price.