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The Secret Lives of Speakeasies

Decades before Prohibition, the unlicensed saloons of Pittsburgh flouted state liquor laws, fomented social movements, and started a national trend.


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Bottles and barrel of confiscated whiskey (circa 1920-1932). Photo by National Photo Company Collection/Library of Congress.

Whisper “speakeasy” into a search engine of your choice and odds are you will stumble across the story of Kate Hester, the Pittsburgh hotelkeeper at the center of the amusing, possibly apocryphal origin story for the word.

Hester appeared in what can only be described as a prototypical trend piece for The New York Times in July 6, 1891. The story goes like this: Hester owned a saloon in McKeesport, just southeast of the city, that sold booze in defiance of a state law that upped the costs of licenses for alcohol so much that it was nearly prohibited. When customers got too rowdy, Hester would hush customers with “speak-easy, boys!” to avoid attracting the attention of authorities; the expression soon spread to the city, and the nation. “Some day, perhaps, Webster’s Dictionary will take it up,” the yarn concludes.

From the Monday, July 6, 1891 edition of The New York Times. Photo from TimesMachine.

The Oxford English Dictionary did take it up: It pegs the first publication of the word referring to an illegal bar to the New York Voice in 1887.

Daniel Okrent, the author of Last Call: The Rise and Fall of Prohibition, suggests the term is older than that, and it probably jumped the Atlantic: It shows up in James Joyce’s Ulysses, set in the Dublin of 1904. (“In the speakeasy. Tight. I shee you, shir.”) “It’s an adaptation of the local term, ‘speak softly shop,’ from Ireland,” Okrent tells CityLab. “It wasn't used a lot in the pre-Prohibition days, for the obvious reasons. Those saloons were legal.”

But Pittsburgh does play a key role in the genesis story of the American speakeasy, those forbidden drinkeries of the Prohibition days that are staging something of a revival among trend-seekers. The details, and the role of the legendary Kate Hester, remain a matter of some debate. To separate fact from fiction, let’s head to the Steel City and order something stiff.

Bar milk and punch at Acacia, a Prohibition-themed speakeasy/bar on Carson Street in Pittsburgh. Photo by Andrew Small/CityLab.

The Hester story puts Pittsburgh on the map as a prototype for the precarious permissiveness we see in cities before Prohibition. While the Volstead Act, which prohibited the production, sale, and transport of liquors, would not be enacted until 1920 in anticipation of the Eighteenth Amendment’s passage, the temperance movement in the U.S. began to get dry laws on the books in the late 19th century. A Pennsylvania law enacted in 1888 called the Brooks High License Act limited alcohol sales with high-cost licensing and restricted the hours of operation for bars. Licenses cost between $200 and $500 and there were $50 fines for operating without a license or selling liquor on Sundays. High license policies also sprouted up in 14 other cities, such as Chicago, Boston, St. Louis, and Omaha, as the temperance movement built political momentum.

By 1890, Pittsburgh had roughly 700 speakeasies and just over ninety licensed liquor dealers, according to James Fernald’s 1890 publication The Economics of Prohibition. Here’s a map of a group of people who pleaded guilty to operating a “disorderly house” in the Pittsburg Dispatch in May 26, 1890.

No knock required: The unmarked entrance to Acacia. Photo by Andrew Small/CityLab.

While the temperance movement had progressive roots, it was also a manifestation of an earlier era’s version of the rural/urban divide, with “wet” cities operating in “dry” states. “The difference between Prohibition enforcement in cities and the rest of the country was enormous, it was night and day,” Okrent says. “The same federal law, the Volstead Act, in a small town in Indiana bore no relationship to the same law as it was enforced 100 miles away in Detroit or Chicago. Generally, the larger the city, the closer to an international border or ocean, and the larger the Roman Catholic population, the less likely that the laws were enforced. The ‘wettest’ cities [during Prohibition] were Detroit, New York, New Orleans, and Baltimore.”

The interior of Acacia during the early hours of the day. Photo by Andrew Small/CityLab.

In those places, cultural tolerance and political connections kept the booze flowing. Alderman and councilmen were often tavern owners, especially in cities where Catholic political machines ruled the day with large constituencies of Irish- and Italian-Americans. “The mythology we have from movies of the password and the peephole—in a city like New York or Detroit, that was gone by 1922 or 1923,” Okrent says. “Illegal places operated by bribing local officials if they needed to and often they didn't need to, they were very much out in the open.”

While the drinks seemingly never stopped, Prohibition did bring about one big change: It brought men and women together in drinking establishments for the first time. “The [19th century] saloon was a male-only institution. Men and women didn't drink together in public, except for the wealthy in hotel restaurants,” Okrent says. “Once you have Prohibition in 1920, the illegality turns it into a sport to go to these places.”

Even with that societal change, Sismondo says our modern image of speakeasies is still a little off: The majority of them were anything but glamorous. “Proper cocktails emerged towards the end of the 1920s because these places weren’t really set up to operate that way,” she says. “It was more likely a bunch of guys drinking a bottle in a dark basement. It wasn’t ritzy.”

The Omni William Penn Hotel in downtown Pittsburgh, where an original Prohibition-era bar was discovered a few years ago. Photo by Andrew Small/CityLab.

Back in Pittsburgh, I stop by the bar in the basement of the William Penn Hotel. It’s called the Speakeasy, and there are excerpts from the 1891 New York Times featuring Kate Hester on the drink menu. Those quotes accompany pictures of police pouring liquor down street gutters, dapperly dressed dudes standing next to a trove of forbidden booze, and mustache-bearing distillers eyeing their latest concoctions of ethanol.

Dawn Young, a bartender who has worked at the Speakeasy since it (re)opened in 2012, tells me that the bar’s existence was only revealed when hotel renovations knocked down a wall. Today, visitors can reach the bar from the front entrance of the hotel, whereas the original path would have led to a side-entrance on Oliver Avenue.

A bourbon old-fashioned and peanuts at the bar of The Speakeasy in Pittsburgh. Photo by Andrew Small/CityLab.

In this swanky underground den, I meet John Schalcosky, an amateur historian who runs a Facebook page about eccentric Pittsburgh history. I reached out to Schalcosky to dig up whether there was any evidence prior to The New York Times piece about Hester’s involvement in speakeasies. I had already found her (and her children) in the 1900 Census via Ancestry.com, listed as a hotel keeper in McKeesport, just southeast of Pittsburgh. Here are some of her details I transposed from the Census ledgers:

Kate Hester’s entry in the the 1900 McKeesport Census. Photo by Screen shots from Ancestry.com/CityLab.

Address: 243 Fifth Avenue
Date of Birth: November 7, 1855
Age at time of census: 44
Married, widowed, or divorced: widowed
Mother of 9 children
Born in England, mother and father born in Ireland
Year of immigration to the United States: 1860
Number of years in the U.S.: 40
Occupation: Hotel Keeper
Can read, write, speak English: yes, yes, and yes
Own or rent: rent
Home or farm: home

Schalcosky has a theory for why licensing wouldn’t have deterred someone like Kate Hester. “At the time, running an illegal bar would have been an easy way to make money for someone who was a widow like Kate Hester,” he says. “It’s unlikely she would have learned a trade or a skill during that era. No law was going to stop her or anyone else from selling liquor. The average working person was pretty determined to get a good drink after work. People want what they want.”

Schalcosky’s best find: Two years earlier than the New York Times story on Hester, there’s a story in the June 30, 1889 edition of the Pittsburg Dispatch titled “THE SPEAK EASIES” with a later sub-headline that declares the term to be “A PITTSBURG INVENTION.”

The Pittsburgers scoop The New York Times. (Screenshot from The Pittsburg Dispatch on June 30, 1889/Library of Congress).

He also found one of Hester’s colleagues, an earlier character named Mary Murphy who makes the papers for all kinds of trouble associated with “tin-pots” and “doggery” dating as far back as 1869. An April 16, 1889 edition Pittsburg Daily Post reports under the headline: “A Speak-Easy Siren Arrested,” where Murphy gets charged for operating at 727 Forbes Street.

And Kate Hester? “There’s a lot more to that story,” Schalcosky says. He hasn’t found a smoking gun for the “speak-easy” origin myth, but he has obtained a fuller picture of the woman who told those patrons to hush.

Hester’s booze-related activities appear four times in the Pittsburgh Daily Post and once in The Pittsburgh Press. In a December 16, 1890, edition of the Daily Post, Hester is among a list of “ignored bills” at a hearing for selling liquor without a license. In April 10, 1891, her “defective” application for a liquor license was given a hearing and she “produced a letter from her pastor giving her a good name.” (A colorful April 8 account in The Pittsburgh Press describes the license process as if it were a baseball game: “Mrs. Kate Hester made a strong play last year, but she was knocked out just when everyone thought she was going to score. She came to the bat this morning looking just a little shaky.”)

Even so, Hester’s local celebrityhood seems to have been limited; she’s mentioned as one of many plaintiffs against a pickpocketer in a March 1895 Pittsburgh Post-Gazette story and as one of the people injured on a McKeesport streetcar accident in the June 1899 Pittsburgh Daily Post without much notice of her infamous speakeasy past.

In December 14, 1903, Hester finally appears to have received legal clearance to run her bar, as this rather cryptic dispatch in the Pittsburgh Daily Post describes an incident of smallpox at her Fifth Avenue Hotel in McKeesport.

(Screenshot from the Pittsburgh Daily Post on the Pittsburgh Post Gazette archives)

Having gone legit, Hester did not seem to have success passing the family business on to her daughters. In the June 7, 1904 edition of the Pittsburgh Weekly Gazette, Miss Anna Hester, daughter of Mrs. Kate Hester, proprietress of the Fifth Avenue hotel, would enter the convent of the Sisters of Mercy in Pittsburgh, joining her two sisters there. The story adds that another one of Kate Hester’s daughters wished to join but “a regulation prevents more than three members of one family from being inmates of the same institution.”

After that, the trail of Catherine E. Lynch, widow of John Hester and speakeasy proprietor, goes cold: The Pittsburg Press mentions a benefit euchre at her home with the Ladies’ Aid Society of St. Peter’s Catholic Church in May 20, 1906 and she’s listed as an attendee of a McKeesport wedding. She died in 1926 at age 72. But there’s no tell-all obituary that references her saloonkeeping fame or her enduring contribution to the nation’s drinking culture.

I ask Schalcosky what he thinks is behind the renewed allure of speakeasies today, given the absence of legal prohibitions on alcohol. “I think it has to do with trying to connect with our communal past,” he says. “People appreciate a good tale and location to go along with it. That, and our timeless love for alcohol.”

Andrew Small is a freelance writer in Washington, D.C., and author of the CityLab Daily newsletter (subscribe here). He was previously an editorial fellow at CityLab.

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This post originally appeared on CityLab and was published April 19, 2017. This article is republished here with permission.

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