Riley St, Surry Hills

G’day, Charles Touma here and today, I’m on Riley Street in the magnificent Surry Hills to talk about the most notorious individual to ever live here, a woman who became known as, “The worst woman in Sydney”. Her house at 104 Riley Street became the centre of the Sydney underworld for two decades. Kate Leigh was born in Dubbo in 1881, and after a troubled childhood, she moved to Sydney where she married an illegal bookmaker, Jack Lee. Her husband was soon jailed for assault and sentenced to a long stretch in Long Bay Jail. Kate became a lady of the night and soon established her own brothel where she was originally the star attraction, but soon became the madam. She attracted the eye of another criminal, Samuel “Jewey” Freeman, who had grown up in Frog Hollow, which was known as one of the worst areas of Sydney.

Frog Hollow stretched between the sheer cliff on the Western side of Riley Street and Ann, and Albion Street. Freeman had made a career from armed robbery as leader of the Riley Street gang at the time when other gangs, particularly “The Big Seven” and the “Forty Thieves”, were his main rivals in criminal enterprise. In 1914 Freeman and the Riley Street Gang attempted Australia’s most audacious crime, an armed robbery on the payroll for the Everleigh Railway Workshop, using a getaway car which was unheard of in Australia until that day. The Everleigh Street Heist was pulled off by Freeman and his sidekick, “Shiner” Ryan, wearing handkerchief masks and driving goggles. They held up the horse driven carriage at gunpoint, which was carrying the £6,000 of railway payroll. The getaway car was pursued by one of the railwaymen on horseback, but the horse couldn’t keep up.

Freeman planned to escape to America with Kate and his winnings but unfortunately, his colleague, Shiner Ryan started spending big around town, including diamond jewellery for his girlfriend. When he was arrested and charged, only £600 was recovered in a stored glass jar in his Surry Hills home. Soon after “Jewey” Freeman was arrested and the ensuing court case, Kate Leigh perjured herself by giving Freeman an alibi. As a result, she was sentenced to five years in Long Bay Jail. Kate Leigh and her gang rival, Tilly Devine were the main protaganists in the TV series, “Underbelly: Razor,” broadcast over 13 episodes on the Nine network. Now I have been selling in Redfern and Surry Hills for 20 years and one of my recent sales, number 477 Riley Street, just down the road, a three bedroom terrace, which I sold for $2,510,000 a few months ago. In my next video, I’ll be covering the end of Kate Leigh’s criminal enterprise story which includes properties all over Surry Hills, including on Devonshire Street and Landsdowne Street. Now my name’s Charles Touma. My office on Thurlow Street is always open for you to come in and have a chat.