10 Beautiful Broads Connected To The Mob

The world of organized crime has always been shrouded in mystery and intrigue, with tales of power, loyalty, and betrayal capturing the public’s imagination. While the spotlight often shines on the notorious mobsters themselves, the women who stood by their side — whether as lovers, wives, or partners in crime — have equally fascinating stories. In this article, we delve into the lives of ten beautiful and captivating women who were connected to the mob, uncovering the allure and complexities of their relationships with some of the most infamous figures in organized crime.

Virginia Hill

Associated with: Bugsy Siegel and Joe Adonis

She was sassy, she was smart, she was well dressed — and she was good looking. To start any mob molls article off without featuring Virginia Hill would be pointless.

Most people who aren’t even mob aficionados have heard the name, most notably because she was the glamorous girlfriend of hot-headed mobster Bugsy Siegel, and of course for the controversy surrounding his death in 1947. Prior to Bugsy she also dated Joe Adonis, an important mobster who had a hand in the formation of the modern Mafia structure. The Flamingo was allegedly named after Virginia Hill — a nickname Bugsy used to call her. Hill died in mysterious circumstances in 1966 at the age of 49 from an overdose of sleeping pills.

Dona Drake

Associated with: Louis “Pretty” Amberg

Dona Drake went by many stage names in the 1930s and 1940s. She was a successful dancer, singer and film actress, and she was beautiful. It’s no surprise that she gained the interest of many male admirers, one of them being mobster Louis Amberg — active in the 1920s and early 1930s trying to take over Brooklyn’s racketeering scene against the likes of Louis Buchalter and Jacob Shapiro. Amberg was found in a burning car in 1935. Drake claimed she only knew him as “Mr Cohen.” Incidentally Amberg died just hours before Dutch Schultz on 23rd October 1935.

Janice Drake

Associated with: Anthony “Little Augie Pisano” Carfano

Janice Drake was a dancer who gained the title of Miss New Jersey in 1944 and the former wife of comedian Allan Drake. Her final love interest, mobster Anthony Carfano, would be responsible for her death — although not directly. Carfano was driving home when they were both shot to death by two Genovese hitmen. Vito Genovese ordered Carfano’s murder because Carfano refused to meet with him after he took control of the Family in 1957. The only reason Janice Drake was murdered was because she was in the car — the killers could not leave a witness. An unfortunate case of wrong time and wrong place.

Lottie Coll

Associated with: Vincent “Mad Dog” Coll

Lottie Kreisberger was a fashion designer in New York who married Vincent Coll in 1932 shortly after his acquittal from a case involving the killing of five-year-old Michael Vengalli in a botched drive-by. She would spend just a few weeks with Vincent before she was made a widow when he was killed in early February 1932. Both Dutch Schultz and Owney Madden had put a $50,000 bounty on Coll’s head. Lottie was later convicted of carrying a concealed weapon and sentenced to 6 months in prison, fearful that her husband’s killers would come after her too. Not much is known of what happened to her after the mid-1930s.

Bonnie Parker

Associated with: Clyde Barrow

No list like this is complete without Bonnie Parker — the legendary companion to Clyde Barrow, just 23 at the time of her death in 1934. She had previously married high-school sweetheart Roy Thornton in 1926 when she was just 16 and was still wearing his ring when she died, having never divorced him. In 1930 she met Clyde Barrow and helped smuggle him a gun into prison. When he was released two years later she decided to join him as an outlaw. After their notorious crime spree they were ambushed and killed by law enforcement in May 1934. One gang member later testified he never saw Bonnie fire a shot.

Marion Kiki Roberts

Associated with: Jack “Legs” Diamond

Marion Kiki Roberts was the gun moll of Jack Diamond — a man who seemed to have more lives than a cat, evading assassination attempt after assassination attempt. She was one of the last people to see Jack “Legs” Diamond alive and was hauled in for questioning over his 1931 murder. The publicity helped her career at first, but gigs became few and far between by the mid-1930s. Kiki Roberts vanished from news sources by the end of 1936.

Viola O’Banion Kaniff

Associated with: Dean O’Banion

Helen Viola Kaniff was the wife of North Side gang leader Dean O’Banion. They married on February 5, 1921, and soon bought into William Schofield’s flower shop — a legitimate front for Dean’s criminal operations and North Side gang headquarters. It would also be the place his life would end just three years later at the hands of Frankie Yale and Genna gunmen John Scalise and Albert Anselmi. Viola never got over his death and died in Chicago in 1976, aged 75.

Evelyn “Billie” Frechette

Associated with: John Dillinger

At the age of 26, Evelyn “Billie” Frechette fell in love with notorious bank robber John Dillinger. She stayed out of his crimes — apart from once driving him to a doctor when he was shot — and had planned to marry him but never completed divorce proceedings from her previous marriage before Dillinger was killed. Arrested in April 1934 for harbouring a criminal, she spent two years in prison. Dillinger was killed in July 1934 while she was still inside. She died on January 13, 1969, after a battle with cancer.

Helen Gillis

Associated with: Baby Face Nelson

Helen Gillis was the wife of Lester Gillis, aka Baby Face Nelson. Unlike many other women here, she was an active member of the gang. After Dillinger’s death in the summer of 1934, she joined Baby Face and John Paul Chase as they continued — which ended when Baby Face was fatally shot in a police shootout, dying in Helen’s arms hours later. She surrendered two days later and was sentenced to a year and a day in prison. Helen went on to pass away in 1987.

Gay Orlova

Associated with: Charles “Lucky” Luciano

Last on our list is the stunning Galina Orloff, born in Russia, who came to America at the young age of 16 following the American dream — and achieved it, appearing on Broadway and in newspaper and magazine columns. She managed to stay in the USA after her visa ran out by marrying a balcony usher who fell madly in love with her. By 1935 she had met Charles “Lucky” Luciano, but he was soon sent to prison and Orlova was deported to Paris.

She was still trying to win him back when Luciano was released in 1946, but her request to see him in Italy was refused. Lucky, just two years later, went on to meet Igea Lissoni in 1948 — the woman he would call the love of his life. As for Orlova, her fate remains unknown. There is a rumour she died by suicide in the late 1940s.

→ Read the Full Gay Orlova Biography

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