Visit Sydney Australia

Tom Roberts' 1895 painting Bailed Up depicts a Cobb & Co hold up from the 1860s.

Sydney's Bushramgers

As Sydney started life as a dumping ground for the worst of England's criminal system during the late 18th and early 19th centuries, from its beginnings it was a soc xiety outside of the law. The majority of early immigrants were convicts or their keepers, resentful of authority and the harsh conditions of life in the hulks and penal settlements of New South Wales and Van Diemen's Land (now Tasmania). Bushranging in Australia began in and around Sydney, the earliest being convicts who had escaped from assigned service on government or private farms. Known as bolters, they were alone in rough country without posessions. They 'bailed up' travellers and robbed farms for money, horses, food, guns and clothing, more to stay alive that to gain wealth. Most had little chance of surviving in the bush. Few lived long in freedom, dying of starvation, sickness or exposure, or were killed by the police and landowners. Those who were captured alive were hanged or flogged or died in prison or exile. Some of the earliest recorded bushrangers were a group of escaped convicts who were found living as bandits in the Hawkesbury district as it was officially being opened up for farming. In 1796 three of them were shot in the act of robbing large parties of Aborigines.

The term "bushranger" was in use at least as early as February 1805 when the Sydney Gazette reported that a cart had been stopped by three men "whose appearance sanctioned the suspicion of their being bushrangers". The word was used to describe those who left the colony to range the bush. From 1805 onwards it was applied to criminals who attacked people on the roads or in the bush. The term "bolter" was first used in Tasmania to describe convict escapees through the term is now used to describe all Convict bushrangers.

By 1800 many bolters and sheep-stealers were at large in the Sydney region, the most well known of which are listed below. On 15th June a proclamation declared the outlawing of these bushrangers, and as a result three men were arrested and sentenced to death. A General Order issued on 24 July 1813 required all persons to "assist in apprehending strollers and take them before a magistrate". At the time that bandits were infesting the Liverpool and Parramatta roads and Gov. Macquarie instructed that a military party and constables be sent out to deal with them. In 1814 a gang of about 17 bushrangers were reported to operating at the Cowpastures in the Campbelltown district. Gov. Brisbane offered a reward of £5 for each bushranger apprehended. By 1830 bushranging had become so great an evil that the Legislative Council passed an Act to deal with it. Though the Act carried a death sentence it did little to discourage the practice of bushranging.

In the latter part of the Colonial era there was a second wave of Bushrangers whose activities were centred in the lands west of the Great Dividing Range - the country now traversed by the highways of New South Wales, Victoria and Tasmania. Unlike the bolters, the 'Wild Colonial Boys' were in the main, Australian born, free men who became bushrangers by choice, born in the bush with expert knowledge of horses and firearms, and the plains and mountain ranges they roamed in search of fortune and adventure. They had little regard for authority and no sympathy for weakness. Their target was gold, the discovery of which in the 1850's led to numerous goldrushes and presented ideal circumstances for the exploitation their skills and delinquency. Names such as Ned Kelly and Ben Hall became synonimous with this era, they being romanticised in comic s and newspaper articles, helping trigger the Larrikin element seen today as an essential part of Australia's national personality.

John Cesar (Black Cesar)
A First Fleet convict, John Cesar was probably Australia's first bushranger. A native of Madagascar, he was an ex-slave from The West Indies who somehow had escaped and reached London. Not being able to find a job he became a petty thief and pickpocket. He was caught and transported for 7 years and left England per Alexander aged about 23 at that time (May 1787). His occupation was listed as servant or labourer. It was said of him that "he gave more trouble than any other convict in the settlement". Cesar was a big man who needed more food to survive than the meager daily ration being issued to the convicts because of the shortage of food. Therefore it was probably more in desperation than for any other reason that he proved to be such of a nuisance. Occasionally he was joined by other bolters, either stealing food and clothing or living on whatever fish and game they could catch, possibly helped on occasion by Aborigines.

His first brush with the law in the colony was in April 1788 when he was accused of the theft of a loaf of bread. A year later he was back in court in the company of an Aborigine called Black Jimmy charged with theft, having been captured by a convict, a cooper named William Saltmarsh. Cesar was found guilty and sentenced to life on Norfolk Island and given 500 lashes. He promptly escaped and 2 nights later " stole a musket, cooking pot and rations. Two weeks later he robbed the brickmakers of provisions at Brickfield Hill. 23 days after bolting, on 6th June 1789, he was taken captive again after being caught him stealing vegetables from the assistant commissary's garden. Governor Phillip set him to work in chains tending a vegetable patch on Garden Island and in concession to his ravenous appetite he was given vegetables from the garden to supplement his normal ration.

In December 1789, Ceasar stole a canoe and escaped under cover of the night from Garden Island. He gave himself up a month later at Rosehill (Parramatta), having been badly wounded when he tried unsuccessfully to join up with Aborigines. In March 1790 %k, he was condemned to death but the Governor took pity on him, bestowing a pardon and sending him to Norfolk Island to serve his original sentence there. In 1793 he was allowed to return to Port Jackson but by July 1794 Cesar had taken up his former practice of subsisting in the bush by plundering the outlying settlements. He was re-captured and sentenced to hard labour, only to escape again in December 1795.

Around that time, Aborigines were raiding farms between Parramatta and Prospect Hill. Cesar took on the Aborigines' leader, Pemulwuy, cracking his skull. Although seriously wounded, Pemulwuy recovered but was killed during another clash in 1802. Through briefly acclaimed as a hero, Cesar soon went back to plundering the farms and huts on the outskirts of Parramatta. He was captured and flogged again only to head for the bush once more. Lore has it that a free settler named William Blakehurst had captured him and received a reward of five gallons of rum. The drinking spree with his mates turned nasty and Blakehurst had a similar reward placed on his head after he drove an axe into the skull of one of them. This may be more fantasy than fact as Judge-Advocate Collins' journal relates the circumstances of the capture differently.

Gov. George Hunter issued an order on 29th January 1796 offering a reward for the capture of Black Caesar and warning settlers against providing miscreants with ammunition. "Notwithstanding the reward," wrote Collinss, "black Caesar ... remained at large, and scarcely a morning arrived without a complaint being made to the magistrates of a loss of property to have been occassioned by this man. In fact, every theft that was committed was ascribed to him". Second fleet transportee John Winbow and another man set out to claim the reward. On 14th February 1796, they tracked Cesar to thick scrub at Liberty Plains near Strathfield and laid in wait all day for him to appear. The following morning, Cesar emerged, realised his position and responded by reaching for his musket but Winbow shot Cesar first. He died a few hours later, age 32.

William Knight
One of Sydney's original bushrangers, Knight was one of the first convicts to bolt. Having arrived in Sydney per Neptune in 1790, he went bush within weeks of his arrival, commiting robbery as and when he needed to, sometimes with accomplices, other times on his own. It was one of his accomplices who murdered John Leighton (Jack the Miller), who operated a mill on Millers Point. Knight, from Middlesex, England, was transported to NSW on the second fleet , arriving per Neptune in June 1790. Between May to November 1801, a reward was offered for his apprehension.

James Warwick
Warwick, from Southampton, England, was transported to NSW on the third fleet per Matilda, arriving in Sydney in October 1791. He was an early convict escapee who made a nuisance of himself stealing from farmhouses to keep himself alive. He worked alone and at times with accomplices. A reward was offered for his apprehension on 11th May 1801.

William Geary
Leader of a gang of bushrangers who operated throughout the Parramatta, Windsor and Castle Hill districts. Geary was setenced to transportation to NSW in 1812, arriving per Surrey in August 1814 and sent to Windsor for distribution. Three years later, he was taken prisoner, tried and found guilty of the stabbing murder of two men. A violent man believed to be insane, he was sent to prison at Newcastle, arriving on Lady Nelson on 18th October 1818. Four months later he escaped but was recaptured soon after. It was discovered that he had planned a murder with a fellow prisoner. Within a year, Cleary had escaped again and embarked on bushranging activities with John Mills and Samuel Beckett. He was re-captured on 15th February 1821. Sentenced to life ; inprisonment, his plan to escape from Sydney Gaol was detected and foiled. Eight weeks later he suceeded and continued his bushranging activities. His activities were shortlived, he was soon re-captured, and exceuted on 24th August 1821. Geary is remembered by Geary's Cave on Gordon Creek, Gordon, which the bushranger is said to have used as his hideout.

William Pitt
Edmund Burke and Charles James Fox persuaded Pitt to join them around 1815 with a promise of making a quick fortune by highway robbery and then settling down to a life of luxury with a girl of his choice. The trio left their farm jobs and embarked on a life of crime together, working the area between the Georges and Hawkesbury Rivers, successfuly alluding the police for a number of years. The police worked hard to locate their hideout with little suc 1cess until 1826 when a Newfoundland dog the trio had stolen escaped and found its way home. With the help of the dog, the police found them living on their own farm in relative luxury with three women they had abducted from homes they had plundered. The men had armed the women and the police had to call for reinforcements to ensure their capture. The women were set free after pleading they had been kept under duress, the men were tried and hanged at Parramatta.

John Donohoe (alias "Bold Jack Donohue")
Sydney's most famous bushranger, John Donohoe, was immortalised as Jack Doogan in the bush ballad, "The Wild Colonial Boy". Born in Ireland in about 1806, Donohoe was found guilty of intent to commit a felony and transported to NSW, arriving in Sydney on 2 January 1828 per Ann & Amelia. He was first assigned to John Pagan at Parramatta but ended up on a chain gang for misbehaviour. He escaped with two men named Smith and Kilroy from a farm at Quakers Hill and the trio began robbing travellers on the Sydney to Windsor Road. Donohoe was captured and sentenced to death but he escaped while being escorted from Windsor Courthouse to Sussex Street Gaol. His companions who were hanged.

Donohoe teamed up with a variety of characters including William Underwood (see below) during a period of bushranging . His main area of activity was between the Hunter River Valley and Liverpool but committed robberies at Bathurst, Yass, Burrungong, Campbelltown and Liberty Plains (Strathfield). During this period he was nicknamed "The Stripper", either because he made people take their clothes off, or because h e stripped them of everything they possessed. A hero among the oppressed convict chain gangs who referred to him as 'Bold Jack Donohue', he developed the reputation of a modern day Robin Hood. A short man with freckles, blonde hair and weak blue eyes, Donohoe often tormeted his victims and reports indicate he burnt one squatter alive. A reward of £20 was offered for his capture, but this was extended to an offer of 'An Absolute Pardon and Free Passage to England, or a grant of land' as his activities continued.

Eventually he and the gang were surrounded by a detachment of soldiers at Bringelly near Campbelltown on 1st September 1830. When Private Muggleston caught up with him, he took off his hat, waved it in the air three times and shouted, "Come on you ****** , We're ready if there's a dozen of you." Muggleston brought his reign of terror to an end with a shot through the head.

The legend of 'Bold Jack Donohue' lived on in a song composed in 1831. Tradition has it that Governor Darling tried to put down the singing of the ballad by having it banned as seditious so the name in the song was changed to Jack Doogan to allow the song to still be sung. The gorge of Darling Mills Creek, which is now within Excelsior Reserve, was used by Jack Donahoe as a hideout during his bushranging days.

William Underwood
Underwood was leader of a gang which operated in the Nepean, Hawkesbury and Parramatta Districts for the best part of a decade. His accomplices were John Walmsley, George Kilroy, John Webber, William Smith and others from time to t 4ime such as John Donohoe. Webber was shot dead by a trooper in 1830 at the same time as Donohoe whilst accompanying him. Walmsley, Kilroy and Smith were captured in 1831. Walmsley turned informer and escaped prosecution, Kilroy and Smith were found guilty and hanged at Darlinghurst Gaol in 1832. Underwood escaped but was shot dead a year later.

John Jenkins
Jenkins was a bushranger who roamed the area now occupied by Sydney's western suburbs, holding up travellers and relieving them of their money and valuables. He worked alone and at times with others, like the fateful day in 1834 when he joined Edward Brace and Thomas Tattersdale in the robbery of Dr Robert Wardell who had a deer park near Prospect. The robbery went wrong and Jenkins killed Dr Wardell. Not wishing to be party to murder, Brace turned police informer and Jenkins was caught. He and Tattersdale were hanged on the gallows of Darlinghurst Gaol.

William Hutchinson
A resident of Hyde Park Barracks, Hutchison escaped in 1836 and embarked on a four year crime spree in the Penrith-Windsor districts which was interspersed with work on local farms. Hutchison kept a fairly low profile and would have remained at large for much longer were it not for a chance encounter with one of his victims during a visit to Sydney town where he was arrested, sent back to gaol and had his sentence extended.

William Lynch
An escapee from Norkfolk Island, Lynch worked the bush around the Liverpool area with fellow escapees John McCann and James O'Donnell. In 1842, the trio held up Mr Campbell on Dog Trap Road (Woodville Road) at present day Old Guildford. Campbell returned to Parramatta and reported Yhis crime. Chief Constable Ryan, eager to catch Lynch, dressed himself in plain clothes and along with an assistant constable set a trap for Lynch. Ryan and his assistant were bailed up as they passed along Dog Trap Road. Ryan pulled a pistol on them and placed them under arrest, finishing their bushranging careers and sending them back to gaol.

William Mackie
John McMahon, Charles Ross and Mackie bailed up the mail coach on Gt North Road in October 1862. They were soon caught but on their way to Sydney by train for their trial, Mackie escaped. He continued his bushranging activities, at times with Charles Rutherford and Robert Johnstone, at times by himself, holding up the mail coach on Gt North Road a second time in January 1865. He was recaptured and had his sentence extended. McMahon and Ross were given gaol sentences. Johnstone was capture \d with Mackie after they pulled off the latter's second Gt North Road mail coach robbery and were given extended gaol sentences. Rutherford was arrested in 1866 but broke out of Bourke gaol on two occasions before moving to Narrabri where he continued his bushranging activities.

William Willis
Willis, James Booth and Thomas Hampton were some of the last men to engage in bushranging in the Sydney region. On 10th April 1866 they held up the Campbelltown mail coach near Minto. Not long after they held up the Singleton to Musewllbrook mail coach in the Hunter Valley but made the mistake of going to Sydney to celebrate their good fortune. They were recognised by passengers from the Campbelltown coach, police were called to the hotel where they were drinking and they were arrested. All three served eight year gaol sentences.