Where are the women bootleggers in Pittsburgh crime history?

Where are the women bootleggers in Pittsburgh crime history? Sure, many Pittsburgh crime chronicles hit the high points of some of the city’s better-known women of vice, like North Side madam Nettie Gordon and jailbreak mistress Kate Soffel. McKeesport saloon owner Kate Hester, whom popular culture credits with introducing the word “speakeasy,” is another. Many others, however, have been ignored or forgotten.

During and after Prohibition, Goldie Lerner, Freda Pope and Jennie Friedman made headlines and history by producing, moving and selling liquor and beer. Lerner founded a crime family dynasty that spanned more than 60 years, and Pope ran roadhouses and saloons throughout the region. Friedman was former Pittsburgh Mayor Sophie Masloff’s mother. 

Together, their stories speak to the prominent but unrecognized roles women play in Pittsburgh’s vice history.

“I think you have to go looking for them,” says Leslie Przybylek, a curator at the Senator John Heinz History Center who has written on women bootleggers for the museum’s magazine. 

Because much of the city’s history has been written by men, women have gotten short shrift. 

“In the past there just wasn’t the academic push within things like women’s history,” Przybylek told NEXTpittsburgh.

Though their stories are mostly invisible in published histories, women bootleggers were just as important as their male counterparts. Because of Pittsburgh’s distinctive ethnic history and the development of insular neighborhoods aided by the region’s rugged topography, the city’s women might have played an outsized role in vice compared to other cities.

“This was one of a number of urban industrial cities where —  and I don’t want to overstate this — but there was a certain limited tolerance level for women working in aspects of the trade in a legal sense that you would not have found in many other places,” says Przybylek.

Many of Pittsburgh’s women bootleggers began their careers in legal trades, as shopkeepers and running boarding houses. Some came from European countries where economic traditions supported women running liquor-based businesses. When Prohibition began in 1920, some of these women saw an opportunity to capitalize on the demand for liquor, beer and wine in their neighborhoods.

“It’s about commerce, but it’s also about relationships,” Przybylek explains. “And in many cases, they’d already built the relationships with their neighborhoods, with their clients if they ran a grocery store, for example, or something else.”

The Bootlegging bubbie

Bubbie is Yiddish for “grandmother.” Were it not for many federal and state prosecutions and convictions, Goldie Lerner would have been just another Pittsburgh bubbie. Goldie, her husband Philip and their newborn son Jacob emigrated from Russia to the United States in 1906. 

They settled in the Hill District. Philip worked as a butcher before he and Goldie opened their own Wylie Avenue shop. By 1920, when Prohibition began, Goldie and Philip’s family had grown to five children: Jennie, Joseph, Isadore and Dora all were born in the Hill District.

By 1924, Goldie, Philip and Jacob — by then known as Jake or Jakie — were in the booze business. Raids, arrests, indictments and convictions flowed freely until the end of Prohibition in 1933.

Goldie ran a speakeasy in the back of the family’s butcher shop, while Philip and Jake transported liquor. Goldie bought properties throughout the city, including a South Side apartment building, to launder cash and to provide convenient stash points.

The family’s arrest records read like a film noir script. Some of the most notable episodes included Philip’s 1926 South Side arrest after a police officer who was trying to repair a flat tire smelled alcohol coming from Lerner’s car after approaching him for assistance.

Goldie was a familiar face in county and federal courtrooms. In June 1933, soon after Prohibition ended, she received a suspended sentence in federal court for a liquor arrest the previous year. In reporting on Goldie’s conviction, the Pittsburgh Press described her as “the city’s most persistent dry law violator.”

Goldie and her sons Jake and Isadore (Ike) expanded their criminal portfolio to include numbers gambling. Philip Lerner died in 1935. Ike became a numbers banker and went into business with Goldie bailing other racketeers out of jail.

With a criminal record spanning more than seven decades, Jake Lerner became one of Pittsburgh’s most colorful racketeers. His exploits included bootlegging, numbers gambling, prostitution and assault. Between 1945 and 1962, he allegedly ran a Tucson, Arizona, money laundering operation for the Pittsburgh mob.

In 1942, Goldie bought a fashionable Victorian East Liberty home. She died there in 1955 at age 70.

Roadhouse queen

In 1920, federal Prohibition agents raided August Pope’s West End hotel and saloon. They arrested Pope, his two sons Henry and Leo, and his daughter, Freda. Seized in the raid: 200 cases of whiskey, 11 kegs of “vinous and spiritous intoxicating liquors,” and 50 bottles of “assorted intoxicating liquors” stored in a garage a block down Main Street.

The feds threw the book at the Popes. The case yielded Pittsburgh’s first major Prohibition conviction: a $1,000 fine for August Pope and a day in jail. Law enforcement officials dubbed Freda the bootlegging operation’s “brain.”

Arguing tainted evidence and bad policing, the Popes appealed their convictions and won new trials. A federal court overturned Freda’s conviction in 1923.

By that time, the Popes had moved on to running a roadhouse in North Fayette Township. The Cliff Mine Inn had been run by Mary Mahoney, a widowed Irish immigrant. After Mahoney died in 1911, her brothers sold her hotel and saloon to Scott Township saloonkeeper Frank Seifried. Seifried died in 1921 and by February 1922, the Popes were running the 17-room roadhouse.

As her family’s appeals wound through federal court, Freda became the Cliff Mine Inn’s manager. Pope’s Cliff Mine Inn quickly became a nuisance, spurring complaints from neighbors. Intoxicated patrons leaving the roadhouse began having accidents on dark rural roads. Some of the accidents were deadly. 

In 1922, sales manager Walter H. Brown was entertaining two clients at the Cliff Mine Inn. They had met five women and offered them a ride to the roadhouse where, according to a later lawsuit, “they drank moderately and danced with these women.” Brown, his clients and the women left the roadhouse between midnight and 1 a.m. Their car left the road near the roadhouse and Brown was killed, his head crushed. The passengers were thrown clear and survived.

By 1923, Frank Seifried Jr. was trying to evict the Popes, using alleged lease violations as the basis for his lawsuit. The legal battle between the Popes and Seifried dragged on until the early morning hours of Jan. 12, 1926. A fire destroyed the Cliff Mine Inn a few hours after the last patrons left. Pittsburgh newspapers reported that Seifried was trying to sell the property. Though all of the Popes escaped unharmed, the roadhouse was a complete loss.

Freda married George Hess, another saloonkeeper, in 1927. She had dated future mayor and governor David Lawrence. Freda had become infamous by 1929 when she took over the Riverview Inn, a magnificent establishment built in 1926 on a hillside outside Riverview Park overlooking Marshall-Shadeland.

From the Riverview Inn, Freda moved to Allison Park where she leased slot machine baron Alfred Forney’s Longview Farms. Forney liked to bill himself as a simple farmer, pointing to his large rural acreage. But in the 1920s, he headed a million-dollar slot machine empire and had deep ties to area bootleggers and politicians. 

In 1930, one of the most sensational vice raids in Pittsburgh’s history took place on a floating casino and speakeasy in the Allegheny River. It set the stage for Freda Pope to get her feet wet. Owned by the Eichleay Co. and leased by Downtown burlesque theater owner George Jaffe, the Show Boat had been a thorn in Pittsburgh law enforcement’s side since it opened in 1923 as Bongiovanni’s Floating Palace. 

The May 1930 raid, however, was a turning point in what newspapers had dubbed the “pleasure scow” and what muckraking journalist Walter Liggett called a “floating gambling hell.”  Jaffe was forced to find new people to front the operation, which moved back and forth from a berth near the Sixth Street Bridge to one on the Monongahela Wharf at the foot of Wood Street. 

While running Longview Farms, in 1933 Freda Pope took over the operation and ran the Show Boat until 1936. Her tenure there was less eventful than her earlier Prohibition-era exploits.

Like the Cliff Mine Inn 12 years earlier, fire destroyed Longview Farms in 1938 after a protracted legal battle that pitted Freda Pope against her landlord, Forney. 

After Longview Farms and the Show Boat, Freda put her hospitality skills to legitimate uses. In the 1940s, she and her husband operated Grant’s Hill Tavern Downtown. Freda’s last business before retiring at the end of the 1950s was running the dining room in Shadyside’s Haddon Hall Hotel. She died in 1978 at age 83.

The mayor’s mom

Jennie Friedman is a woman bootlegger whose story remains elusive. Were it not for her daughter becoming Pittsburgh’s first woman mayor, it may never have surfaced.

Friedman settled in the Hill District after arriving in the United States from Romania in 1902. Her first husband, Samuel Nieberg, died in 1915, and in 1917 she married a neighbor, Louis Friedman. Their daughter Sophie was born three months later.

Louis Friedman worked several jobs, including a stint as a courthouse clerk and insurance salesman. Before he died in 1923, he also had income from several Hill District properties that he owned.

Now twice widowed, Jennie was left with a family to raise and bills to pay. She inherited their Roberts Street house and got about $1,000 from her late husband’s estate. Jennie later sold the two-story house at 86 Roberts St. and in 1925 bought another, larger three-story brick house, at 319 Roberts St.

Surviving historical records don’t identify an occupation for Jennie Friedman. In 1921, however, the Post-Gazette cryptically reported on a run-in with moonshine “in front of her place of business.” 

In March 1931, the Post-Gazette reported that Jennie’s home at 319 Roberts St. had been raided. They seized six quarts of moonshine, 33 bottles of beer and one gallon of wine. 

Two months after the raid, for which no records could be found in Allegheny County criminal court archives, Jennie and her son, Morris Neiberg, were indicted, tried and convicted of assault and battery.

Jennie Friedman died in 1962 at age 70. Her death certificate identified her occupation as “housewife.” 

Friedman’s daughter Sophie went to work in Allegheny County government and in 1976 she was elected to city council. As its president in 1988, she became Pittsburgh’s first woman mayor after Richard Caligiuri died in office.