When we talk of bushrangers, most would think of Ned Kelly or Ben Hall, quintessential outlaws firmly placed in Australian folklore.  But these guys were later in the picture, on the edges of settlement in western NSW and Victoria when Sydney had become a respectable Victorian city. 

But what about those early days in Sydney, when most of the surrounds were still bush; what about Sydney’s bushrangers?

As Sydney was the first European settlement, and was made up predominantly of convicts in its first years, you would expect some bushranger activity.  

Indeed, Australia’s first bushranger, John Black Caesar,  was in Sydney.  He had arrived in the First Fleet, an African servant in England before being transported. 

He made his first escape attempt in April 1789, recaptured in June, re-escaped in December and returned to the town after being speared in January 1790.  Sent to Norfolk Island he returned to Sydney in 1793 and escaped again, only to be recaptured. 

Each time he had gone alone, but in December 1795 he escaped and formed a gang, robbing and stealing around the edges of Sydney.  Now a true bushranger he was finally shot and killed at Liberty Plains near Strathfield in February 1796.

Throughout the first thirty years of settlement, bushranging was a serious concern to the Government and people of Sydney.  All the major roads, once they left the relative safety of the town, ran out through wild untamed bush.  For some time it was more popular to get to Parramatta by river then risk the overland journey. 

The papers of the day are full of stories and tales of escaped convicts turned to bushranging. 

Captures of these notorious characters were reported with glee in the Sydney Gazette.  There were so many potential bushrangers by 1821 that the Government offered an amnesty to any escaped convict who was in the bush but had not committed any crime of violence.  A pardon instead of the road gangs to entice them out of the bush.  

Perhaps the most famous of Sydney’s bushrangers was John Donohoe, whose exploits were remembered in folk song and story even before his death. 

Donohoe arrived as a convict in 1825 and was assigned to a farm at Quakers Hill from where he soon escaped.  He turned, with two companions, to robbing along the Sydney-Windsor Road.  Captured in February 1828, his two accomplices went to the gallows, but Donohoe escaped.  He was soon wanted for murder as well as robbery and escaping custody. 

With his new gang he roamed from Bathurst to the Illawarra and the Hunter Valley, although much of his work was around Bringelly and Campbelltown.  Countless rewards were offered for his capture but none would put him in.  In September 1830 his luck ran out.  Police who had been tracking him in Sydney’s west finally came across the gang near Bringelly in the late afternoon and gave chase.  A gun fight erupted and Donohoe was shot twice and killed.  

Before he was even in the ground songs and ballads of brave Jack Donohoe were being sung all over Sydney.  The most famous being “The Wild Colonial Boy”, still occasionally sung in Sydney to this day.