Nearly 100 years later, San Antonio’s Prohibition-era bar endures

The day after Prohibition ended in the United States, one bar in San Antonio was throwing its doors open for the first time. Or, that’s the official story.

The Esquire Tavern, which opened on Commerce Street in December 1933, is the oldest bar on the River Walk (predating the iconic tourist spot by a handful of years) and is among the oldest in San Antonio. But its history may stretch back further than that, according to Director of Operations Stephan Mendez, who tells MySA there was “more than likely” some illegal drinking happening there during Prohibition, though the bar didn’t exactly keep record of its own unlawfulness.

“The story that makes the most sense to me was that they were running like a speakeasy at the time, because it’d be very hard to, you know, open a bar the day once you get the go-ahead — like, oh, OK, here’s a fully stocked bar ready to go. So we have to imagine that it was some sort of speakeasy before that,” Mendez said.

Prohibition began in 1920 with the 18th Amendment to the U.S. Constitution. It banned the manufacture, transportation and sale of liquor, though it remained legal to have a drink. Many establishments got around the new laws by taking their operations underground to speakeasies, where secret code words would gain you access to a cocktail. According to the San Antonio Express-News, The Esquire Tavern had been operating above-ground as a restaurant. But as one waiter tells the tale to today’s diners, folks during that time could enter the bar downstairs by asking for a buzz cut.

Esquire Tavern’s story-filled history on the San Antonio River Walk

In its 92-year history (interrupted only by a five-year hiatus from 2006 to 2011), countless stories about The Esquire Tavern proliferate — that a trap door under the bar was discovered, leading to a room used for gambling, and that excavating during renovations before the Esquire reopened revealed a single, red 19th-century shoe. Ripley’s Believe It or Not gave it the title of longest bar top in Texas in 1988. And Mendez, a former Esquire Tavern bartender, said many of the employees claim to see paranormal activity at night, though he hasn’t seen anything, a point he feels “a little cheated on.”…

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