On July 31, 1923, The New York Times published an article sounding the alarm about an existential threat to the bohemian life of Greenwich Village—Prohibition. The Federal Prohibition Director had initiated an injunction against seven restaurants and bars in the South Village that were repeatedly violating Prohibition laws by serving alcohol. Prohibition agents had quietly gathered evidence for weeks, often relying on tip-offs from neighbors with “anti-Bohemian” sentiments. The seven charged businesses found their entrances padlocked, and state attorneys sought a decree for their closure, requesting a shutdown that would last an entire year.
These establishments often served the artists and outsiders residing in the neighborhood, playing a vital role in fueling the vibrancy of bohemian life that characterized Greenwich Village. The enforcement of Prohibition posed a threat not only to these establishments but also to the freewheeling spirit of Greenwich Village. Today, we’ll explore the histories of these targeted speakeasies and their significance in Greenwich Village’s culture.
Bertolotti’s, 85 West Third Street
More than any other restaurant, Bertolotti’s was a fan favorite in the Village. This Italian restaurant, opened in 1897, was located at 85 West Third Street (the same building that Edgar Allan Poe lived in) and had two floors – a top floor meant for formal dining and a more popular basement bar, which decorated its walls with empty bottles. The restaurant cultivated a loyal fanbase, endearing itself to patrons not just through its good food but also with its affordable pricing. According to the Village Preservation’s report, “The Italians of the South Village“, a complete dinner at Bertolotti’s could be savored for only thirty-five cents, with a modest three cents extra for dessert—an equivalent of $8.61 in 2024.
July 1923 was not the first time nor the last time Bertolotti’s was targeted by the police for Prohibition violations. In 1929, Police arrested one of the owners, Carrie Bertolotti, along with two waiters. Prohibition and the Great Depression both slowed the success of the restaurant’s business, but the restaurant, with several changes in ownership, location, and name, continued well into the 21st century. It closed in 2021 under the name, Volare.
The Red Head, 359 6th Avenue
The Red Head Inn appears to be an alternative name for another renowned speakeasy, The Red Head. Established by two cousins, Jack Kreindler and Charlie Berns, in 1922, this clandestine spot cleverly posed as a tearoom where liquor was discreetly served in teacups at the cost of $1 an ounce. Originally situated beneath the 6th Avenue El at 359 6th Avenue (south of Washington Place), it was rumored that during police raids, the owners employed innovative tactics, such as handles that would tip the shelves, causing liquor bottles to drop into a chute leading to a sewer below. In 1926, Kreindler and Berns, in pursuit of a more upscale clientele, moved their operation to midtown, where their establishment evolved into the now-famous 21 Club, still a thriving nightclub today.
Sheridan Square Inn, 181 West Tenth Street
181 West Tenth Street stands as the sole surviving brownstone from a set of five on the same street, as the others fell victim to demolition during the 1913 extension of 7th Avenue. In 1920, the house was transformed into bachelor apartments, in order to attract returning soldiers from WWI. Two years later, a restaurant emerged on the first floor and basement. Named The Sheridan Square Inn, the place gained immense popularity in 1923 after a dance floor was added.
In 1939, Julius Lombardi took over the establishment, renaming it “Julius” and adorning the building with a large neon orange sign. However, this move led to legal troubles with the pre-existing Julius’ bar, located a block away at 159 West Tenth Street. The legal battle reached the State Supreme Court, resulting in Julius Lombardi’s defeat. Now renamed Julius Lombardi’s, the restaurant operated until 1981. The original Julius’ is still in operation and is now a landmarked site.
Jimmie Kelly’s, 181 Sullivan Street
Jimmie Kelly’s was a popular speakeasy known for its notable clients, including Mayor Jimmy Walker, actor John Barrymore, and F. Scott Fitzgerald. It was started in 1921 by Jimmy Kelly, born John De Salvio, who originally worked as a boxer before he turned to night clubs in the 1910s. Kelly was a political organizer and underworld figure, known for his association with gangsters as well as his prominent position as a captain in the Village Tammany Democratic machine. By the late 1950s, the building was re-purposed as a theater space, named the Sullivan Street Playhouse, and became the off-broadway home of The Fantasticks. In 2005, an extreme alteration of 181 Sullivan Street converted it from a 19th century Greek Revival rowhouse into a glass-fronted luxury condo building.