Finding Jakie Lerner

“805 was a burner. where the hell is Jakie Lerner?” That was former racketeer Sam Solomon’s recollection of Aug. 5, 1930, the day when seemingly all of Pittsburgh bet on a single number: 805. When 805 hit, the city’s numbers bankers scrambled to pay the winnings. Many simply didn’t, and some skipped town to avoid the consequences of not paying. Lerner, Solomon said, was one of them.

Sports historian Rob Ruck published excerpts from his interview with Solomon and other aging numbers figures in his 1987 book, “Sandlot Seasons: Sport in Black Pittsburgh.” The historian told me he never followed up to see what became of Lerner. After reading Ruck’s book last year, I went looking for Lerner.

I found him in a Jewish cemetery in Shaler, buried among strangers in a modest grave.

So who was Jakie Lerner?

Lerner, it turns out, was a bootlegger, numbers banker, gambler and pimp who played a key role in Pittsburgh’s organized crime history. His close associates were some of Pittsburgh’s most notorious gangsters, including the North Side’s Cancelliere family and New Kensington’s Mannarinos. In the 1950s, the FBI speculated that Lerner might be Pittsburgh’s biggest bookie.

More than half a century of newspaper articles, law enforcement files and civil court cases paint a colorful portrait of Lerner and the path he cut through 20th century Pittsburgh. His criminal career tracks with some of the most consequential events in Pittsburgh’s organized crime history, including the 1930 infamous 805 episode.

Jacob Lerner was born in Russia in April 1906. A few months later, his father Philip boarded a ship bound for the United States; two years later, Jakie’s mother Goldie emigrated with him. According to stories passed down in the family, they were escaping violent pogroms targeting Jews.

Goldie had kin in Pittsburgh, and the young family settled into rented Hill District tenements. Philip first appears in city directories in 1909 as a butcher living at 1842 Webster Ave.

The family business

By the 1920s, however, bootlegging became a mainstay family business. Before the repeal of Prohibition in 1933, Philip’s and Goldie’s properties were raided multiple times on bootlegging charges. Goldie appears to have been the ringleader, with The Pittsburgh Press describing her in a 1933 article as “the city’s most persistent woman dry law violator.”

Jakie Lerner’s earliest known brush with the law came when he was 11 and convicted of suborning perjury. Three years later, he and four friends were arrested for stealing more than $200 of tobacco from a Centre Avenue store. Five years later, Jakie was arrested for violating Pennsylvania’s 1923 liquor law. Soon he branched out into gambling.

Most histories of Pittsburgh numbers gambling credit Hill District entrepreneurs Gus Greenlee and Woogie Harris with introducing the daily game, which relied on picking three digits derived from financial markets returns, in the 1920s. Oral histories with Greenlee and Harris’s former partners and family members offer a more detailed picture. The famed Pittsburgh Courier photographer Teenie Harris was the younger brother of Woogie Harris, and the photographer described a white partner being brought into the business by Bill Snyder. That white partner appears to have been Jakie Lerner, whom Snyder bailed out of jail after a 1928 gambling indictment. The bailout is the strongest evidence that Lerner was the bridge between black numbers racketeers and the white immigrants who eventually controlled the city’s gambling rackets.

In 1928, Jakie was married to Gertrude Lubowsky. She was the first of at least four women (and perhaps as many as 11) he married between 1924 and 1952. All of the marriages ended in divorce, with graphic testimony detailing Lerner’s violent verbal and physical abuse. Gertrude was one of two women whom Jakie married, divorced, and remarried. Their second divorce and the salacious testimony given in the case made headlines throughout Pennsylvania in 1929. The Wilkes-Barre Record published a story about it beneath the headline, “Given Second Divorce From Same Husband.”

Testimony from Gertrude and her family in the two divorce cases includes detailed descriptions of Jakie’s illegal enterprises, providing law enforcement officers with evidence of the criminal activities of Lerner and his partners. In 1925, Jakie was running a speakeasy in the back of their rented Hill District home on Soho Street according to testimony from Gertrude, who said, “I was forced to help him.” Her testimony in the two cases included chilling accounts of violent beatings and verbal abuse. “He never said a decent word to me that I can remember.”

Dog tracks and Fox Chapel

In July 1930, a handful of gamblers decided to go into the dog track business. Though Jakie Lerner wasn’t named directly in any of the newspaper articles and court cases, later accounts connect him to the group that founded the Guyasuta Kennel Club. Frank “Froy” Nathan, another Hill District gambler, was one of several partners who backed the construction of an O’Hara Township greyhound racetrack. Nathan by 1930 had become well known for sports betting and for numbers gambling. He later  would graduate to jury fixing and, in the early 1950s, a national bribery scandal involving several high-ranking Truman administration officials.

The Guyasuta Kennel Club rented part of the National Amusement Company’s property between Blawnox and Aspinwall, near the intersection of Fox Chapel and Freeport roads—today’s Fox Chapel Plaza area. In June 1930, the partners hired an Arkansas contractor to build the track and grandstands. July 4 was set for opening night, with nine races scheduled. In the first race, a dog was killed after colliding with a board. During the next race, the electric rabbit malfunctioned and the dogs caught it. Finally, in the third race, several dogs were injured. The rest of the races were canceled, and the track was closed with plans to reopen after safety improvements were made.

Newspapers throughout western Pennsylvania reported on the opening night mishaps and focus on the open betting taking place caught the Allegheny County district attorney’s attention. Robert Park began a campaign to keep the track closed, meeting stiff resistance from other elected officials who wanted the track to remain open. The track ultimately reopened under close surveillance by law enforcement officers, but collapsed and closed permanently by the second week of August 1930—just four days after the 805 number hit.

After all the litigation was settled, a North Side contractor successfully bid to demolish the track and its grandstands. Ads published in the Pittsburgh Post-Gazette in 1931 offered, “All kinds of Yellow Pine Lumber For Sale Cheap.” Though the racetrack became a small footnote in Pittsburgh’s history, the episode led the county to enact stronger gambling laws. And the nuisance perceived by O’Hara Township residents and lack of zoning regulations contributed to their ultimately cleaving part of the municipality off in 1934 to create Fox Chapel Borough.

The war and the west

Jakie spent the 1930s racking up more gambling arrests, marriages and divorces. By then he was known by several names: Jack, Jake, John, and the nickname, Jakie. He also had two aliases, Jacob Feltmere and Joseph Harris. By 1937, the Pittsburgh Post-Gazette was reporting that police had begun describing him as a “big shot in the numbers racket.”

After the United States entered World War II, Jakie enlisted in the army. In September 1942, the Post-Gazette reported on a going away party for him at Oakland’s Webster Hall. A family photo labeled “Mr. Jake Lerner Testimonial” shows Jakie seated next to his mother and surrounded by more than 200 relatives, friends and business associates. Jakie served for a year as a private before being discharged in October 1943 for medical reasons.

A month later, he and a woman named Marion—identified in land records and newspapers as his wife—bought a nine-acre ranch in Tucson, Ariz. There do not appear to be any surviving records of his marriage and divorce from Marion. The following year, he met a Tucson restaurant hostess, Janet McConnell, and the pair married in Las Vegas. Their daughter Sherlyn was born two years later.

During the 1940s, Jakie remained in the Pittsburgh numbers game, running a citywide racket during frequent Pittsburgh visits while also establishing himself in Tucson’s rackets. Arizona newspapers reported several arrests between 1945 and the early 1960s, and in a 1947 memo from the Phoenix field office to the FBI director, the Bureau observed that the Lerner ranch quickly became a favorite getaway spot for Pittsburgh gangsters: “Since he located at Tucson, Arizona several of the racketeers in Pittsburgh have been going to Tucson to visit Lerner instead of going to Hot Springs, Arkansas for the vacation as they did in former years.”

Jakie’s time in Tucson came to a messy end in 1960 when he tried to bribe a police officer who had stopped him for a traffic violation. His daughter, Sherlyn, who was a teenager at the time, said that’s just the way he liked to solve problems. “He got by with that all his life,” she said. “They just did it because in the number business in Pittsburgh or whatever kinds of business they were in, it was always policemen, judges, lawyers, all the top people—they, you know, they just let them get by with that.” Jakie pleaded guilty to a lesser charge in 1961 and was sentenced to a year’s probation.

In 1961, Janet filed what became her third divorce suit against Jake. They already had divorced and remarried. And a second and earlier divorce proceeding had been dismissed. The second divorce decree was granted in May 1962 and Janet continued living in Tucson where she raised their daughter. Janet died in 2016 at age 96; Sherlyn still lives in Tucson.

By the mid-1960s, Jake had become a trusted figure among Pittsburgh’s organized crime families, including New Kensington’s Mannarino family, the LaRocca family, and the Cancellieres. In a 1965 series on organized crime in the city, Post-Gazette reporter Vince Johnson described Jake’s permanent return to the city. “Early in 1964, J.L.—the initials of the man who figureheads the syndicate’s numbers operation in Pittsburgh—left Tucson, Ariz., and returned to this city. His job was to be the Pittsburgh front for New Kensington’s Mannarino Mob.”

End of the line

Jakie’s final run-in with the Pittsburgh police took place in 1981. According to the Pittsburgh Press, two men forced their way into his Oakland apartment and robbed him of $2,000. The detective who interviewed Lerner noticed “a large quantity of numbers slips lying about” and Jakie was arrested on gambling charges.

The next year, on July 13, 1982, Jakie Lerner died at age 76 in the same Oakland apartment. Separated from his family since the 1950s, he died alone.

His 1973 will named three beneficiaries: a longtime friend, Wilbert Darling, to whom he bequeathed a star sapphire pinkie ring; another friend to whom he bequeathed $5,000; and, his attorney, who was to receive what was left over after the estate was settled.

Darling never got the ring. I interviewed him in 2019 in the Squirrel Hill nursing home where he lives. Then 97, he explained that the ring was stolen in the 1981 robbery. “He was in the number business,” Darling said of his late friend. “He was the big man.”

In his later years, the “big man” experienced a precipitous decline. By 1970, he had lost most of his money and alienated many of his partners. Longtime associates remember him wandering throughout the Hill District speaking to himself and accusing friends and relatives of stealing from him. His daughter recalled bizarre behavior that ultimately drove a wedge into their otherwise close relationship.

Darling had an explanation for Jakie’s diminished capacities and behavior: “He had syphilis,” Darling told me. “I guess it affected his brain.”

Leonard Zucco, the son of Jakie’s last numbers partner Tony Zucco, confirmed the odd behavior. Jakie was a close Zucco family friend. Tony had named his youngest son Jake before the pair parted ways in the late 1960s. “He was getting paranoid. I don’t think my father knew the term paranoid, but he [Jake] was getting a little goofy,” Zucco said in an interview from his Tucson home. “He accused everybody of robbing him.”

His divorce records reveal a man so despicable that most of his own blood relatives couldn’t stand him. I asked one of the last relatives alive who knew him if she would have been his friend. She answered, “Oh no, I would have no respect for him. Are you kidding?”

Lerner spent his entire life in crime, but Will Darling told me that he paid for Jakie’s funeral and burial—because his friend was broke when he died.