May 18, 2026
Introduction: In this fifth of a six-part series, James Pylant tells the saga of the Billingsley family in America, a tale involving genealogy, crime and Hollywood. James is an editor at GenealogyMagazine.com and author for JacobusBooks.com, is an award-winning historical true-crime writer, and authorized celebrity biographer.
Here is the fifth article about the Billingsley family. Touching on genealogy, crime, and celebrity, it traces the family connections from Barbara Billingsley of Leave It to Beaver to Peter Billingsley of A Christmas Story, as well as to the owner of the famous Stork Club.
The youngest of Robert Wiley Billingsley’s children, Sherman Billingsley was born in Enid, Oklahoma.
After a variety of adventures, Sherman eventually became a restaurateur, owner of the famed Stork Club in New York City. On 30 June 1951, TV Guide published a short, sanitized profile of Sherman, calling him a “realtor, author, perfume purveyor, neckwear nabob, host and owner of the Stork club” who provided a “glittering atmosphere to a moderately select few at the nation’s most publicized restaurant.”
This profile reports:
The beginnings of this glamorous dispenser of glamour were modest. Billingsley was born in Enid, Oklahoma, on March 10, [1896]. As a youngster, he raised pigeons, gathered empty bottles, and peddled magazines to launch his first business venture, a soft-drink stand.
After a few years in the soft-drink business, Billingsley had $1,000, and he and his brother bought a drug store in Oklahoma City. Soon after, the wanderlust hit him and he wound up in New York with a drug store in the Bronx. He later enlarged his holdings, building houses and garages on a street still known as Billingsley Terrace.
Two friends from Oklahoma put up the money for a three-way ownership, and the first Stork Club was opened on 58th Street, just off Sixth Avenue… Billingsley bought out his partners in 1932.
There is one glaring omission in this pruned biographical sketch: it skips over Sherman’s becoming a teenaged newsmaker during the Billingsley bootlegging bust of 1913.
This article reports:
Upon being arraigned in county court before Judge J. W. Hayson, Friday, Logan and Sherman Billingsley, brothers, who were arrested by county officials Thursday night charged with bootlegging, entered a plea of not guilty and were bound over by the court to await the action of the Oklahoma County grand jury.
The Night and Day drug store on Grand Avenue, where the arrest was made, was closed permanently by Sheriff M. C. Binion, who now has the key to the building in his possession. The Billingsleys are held prisoners in the county jail, to which they were committed Thursday night, having failed to make bond in the sum of $1,000 each, as fixed by the court.
Although Logan Billingsley has been prosecuted by the county on numerous occasions, charged with bootlegging, he spent his first night in jail here Thursday, always having eluded imprisonment by making bond when arrested for previous offenses.
“The Billingsleys were not regarded as ordinary bootleggers because they did not dabble in the business,” a Michigan newspaper explained. They had a small fleet of vehicles to transport contraband between Ohio and Michigan. “The brothers might have called themselves the Billingsley Gang with the reputation they had acquired, but gunplay was never their modus operandi,” wrote Anthony Young. Besides, as Young explained, Sherman “managed to get out of jail by having a good attorney.”
Sherman married 18-year-old Babe McNeal on 3 August 1914 in El Reno, Oklahoma, falsely giving his age as 21. Within a week, Robert W. Billingsley sought to dissolve his son’s marriage, as “17-year-old” Sherman had exchanged vows without parental consent.*
Both the 1900 federal census and his Social Security records reported March 1896 as the birth date, making the groom 18 when he married Babe. Still, he was a minor. The court ruled that the two “have separated and are now living separate and apart from each other; said parties never having cohabited from the time of said marriage up until the present time.” The marriage was annulled on 28 September 1914, though it would not take effect until six months from that date.
On 3 April 1915 – six days after the annulment’s finalization – Sherman married 18-year-old Iva-Dee Risk in Oklahoma. They moved to Seattle, where he opened Stewart Street Pharmacy, which police wrecked in a booze bust. It led to Sherman’s ten-day jail stay and a $100 fine for violating the prohibition law in May 1916. He fared better than his brothers, who faced federal indictments for violating liquor laws.
Local coverage of the “whiskey traffic conspiracy trials” involving the Billingsleys included this photo of the four Billingsley brothers.
The photo caption reads:
The four Billingsley brothers, who are the most conspicuous figures in the prosecution of the alleged conspirators in the trials in the United States district court before Judge Jeremiah Neterer, are shown in this photograph. From left to right: Fred, Sherman, Ora and Logan Billingsley. All but Sherman are under indictment. Sherman came to Seattle from Oklahoma City on subpoena issued at the insistence of the district attorney and is reported to be a material witness in support of the government charges that his brothers received protection from certain public servants in exchange for substantial bribes.
The following year, the Billingsleys expanded their bootlegging enterprise to Michigan with disastrous results. In this next article, Sherman Billingsley is referred to as “smuggler king” and “king of whisky runners.”
Sherman and brother Ora were found guilty of “bringing liquor into Michigan in violation of the federal statute” on 24 January 1919. In a newspaper interview, a tearful Iva-Dee said “stern judges” didn’t know her nice husband. “He’s just a boy, too,” she said, claiming Sherman was 17 when they married, the same age as at his first marriage.
The brothers were unsuccessful in their appeals. However, their sentences (Sherman’s at 15 months and Ora’s two and a half years) in Leavenworth lasted under three months. In 1922, the two were released when a district judge ruled that “their offense was a misdemeanor and therefore punishable with a sentence of not more than one year since they were sentenced only under one count under the amendment.”
The Billingsleys started over in New York City, where Sherman and brothers Ora and Logan built the Theodore Roosevelt Apartments. Soon, another scandal erupted.
In the early hours of 10 September 1925, Sherman found his wife sitting in a car parked at a hotel. She was not alone; a young man was seated beside her. A fight ensued, leading to Sherman’s arrest for simple assault. The other man was a private detective hired to follow Sherman. Iva-Dee testified against her husband, saying that the detective had flashed his badge during the confrontation, but that Sherman struck him anyway. She also said she had not lived with her husband “in some time.”
After a “period of domestic troubles,” Sherman obtained a divorce in Mexico and remarried “almost immediately” to a 23-year-old chorus girl, Hazel Donnelly.
Iva-Dee responded by filing a separation suit, contending that “Mexican divorce decrees are not recognized in New York State.” Iva-Dee explained that she didn’t receive notice of the divorce. She claimed they were happily married until 1923 when her husband became attentive to other women, especially Hazel. Sherman allegedly told his wife that in “nine out of every ten marriages men go with other women.”
The photo caption reads:
Hazel Donnelly Billingsley. This beautiful chorus girl, of No. 1228 Morris Avenue, The Bronx, finds herself ensnared in a complicated divorce tangle. Recently she married Sherman Billingsley, wealthy Bronx builder, it is reported. But Billingsley’s first wife claims Sherman still is her husband, as the divorce, apparently granted in Mexico, is held invalid in this State. Mrs. Billingsley No. 1 is suing for separation.
In October 1925, Sherman and Iva-Dee came to terms, at least financially, which allowed her to continue her suit for separation. In March 1926, Sherman traveled to Nogales, Mexico, for a divorce redo from Iva-Dee and to remarry Hazel. His new wife gave birth to their first child the following month.
Sherman (not unlike brother Logan) reinvented himself when he founded the Stork Club, called “the world’s most famous nightclub” by Life magazine. With his past notoriety bleached, the Stork Club’s founder was called a shy, “local boy” by this Oklahoma newspaper.
At the Stork Club, he met singer-actress Ethel Merman. The two began an affair, and Ethel believed he would leave his wife for her. “The capper came when Hazel Billingsley became pregnant again and Ethel began to contemplate what being a homewrecker might do to her career,” wrote Brian Kellow, author of Ethel Merman: A Life. She ended the affair, telling Sherman she wouldn’t spend the rest of her life being a married man’s mistress.
The Stork Club’s swan song came on 5 October 1965. Exactly one year later, the Chicago Sun-Times announced the nightclub founder’s death.
His widow, Hazel, survived him by 25 years, dying in 1991. Former wife Iva-Dee, who never remarried, died at age 98 in 1995. The fate of Sherman’s first bride, Babe, is unknown.
* “Wedded a Week; Divorce Action Against Wife,” Oklahoma News (Oklahoma City, Oklahoma), 11 August 1914, p. 3.
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Note on the header image: old photos and correspondence. Credit: https://depositphotos.com/home.html [051723]
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