Dolly Gray was the brains behind the bullets of notorious Melbourne gangster Squizzy Taylor

Squizzy Taylor was a erratic pickpocket until his first wife, Dolly Gray, helped make him into a Melbourne crime kingpin.

Melbourne underworld figure Leslie "Squizzy" Taylor.

Dolly Gray is known as a gun-toting, cocaine-selling, sly grog-making brothel owner and the first wife of notorious Melbourne gangster Squizzy Taylor.

But a new book argues Dolly Gray was much more than a gangster’s moll.

Her story is told in the latest episode of the free In Black and White podcast on Australia’s forgotten characters:

In a new book called Dolly Gray: Madam of Melbourne, true crime author Roy Maloy argues she was the brains behind Squizzy Taylor.

Maloy believes Dolly was a business mastermind who transformed Squizzy from an erratic pickpocket with an uncontrolled violent streak into a crime kingpin.

Dolly Gray, brothel madam and Squizzy Taylor's first wife.

Squizzy Taylor in 1922.

“We have this great big idea that Squizzy Taylor was the most celebrated and revered gangster of the organised crime 1920s period,” Maloy says.

“But honestly I believe he was picked up from being a filthy, very unsuccessful pickpocket to being an organised criminal because of the mentoring of his first wife, Dolly Gray.”

Dolly, the daughter of a chimney sweep, was born Elizabeth Charlotte Haines in South Melbourne in 1882.

Maloy says Dolly was 17 when she married her first husband, Hugh O’Donoghue, and she gave birth to two daughters soon after.

By 1907, Dolly was separated, using her new name, and working as a prostitute and selling sly grog out of a brothel in a house she had bought herself in Bendigo.

New book Dolly Gray: Madam of Melbourne by Roy Maloy.

Squizzy Taylor

Maloy believes Squizzy was about 18 when he met Dolly, six years his senior.

“They seem to form this odd family unit, they travel a lot, they follow the horse racing circuit, where Squizzy is pickpocketing,” Maloy says.

“The four of them create such a family bond that the little girls change their last name, from O’Donoghue to O’Donoghue-Taylor.”

True crime author Roy Maloy.

Champion boxer Ted Whiting took on Squizzy Taylor’s gang in the long-running Fitzroy Vendetta war.

Dolly was at the centre of Squizzy’s rise through the underworld and his criminal enterprises.

Tough but glamorous, Dolly ran a lucrative brothel in the notorious Little Lon red-light district in central Melbourne, where she once survived a gunshot to the head.

But she deserted Squizzy and fled to Adelaide with her daughters in 1919 after she was brutally bashed by her husband’s arch-enemy, boxing champion Ted Whiting, and his men during the gang war known as the Fitzroy Vendetta.

Dolly lived out the rest of her life as “Lottie Haines” in middle-class obscurity – outliving Squizzy, Whiting, and all the key figures of the Fitzroy Vendetta.

“She was so successful at hiding that when her first husband died in the war, by about 1921 his medals are ready to be repatriated to family, and the military couldn’t even find her,” Maloy says.

To learn more, listen to the interview in the In Black and White podcast on Apple Podcasts, Spotify or web.

See In Black & White in the Herald Sun newspaper Monday to Friday for more stories and photos from Victoria’s past.