*** Revised and updated (2021) ***

William Westwood’s tale is one of a misguided youth who finds himself whisked away from all he held dear to endure a lifetime of punishment and lawlessness in Australia. He took to the bush as a teenager and soon became one of the most renowned highwaymen in Australian history under the pseudonym Jacky Jacky (alternatively written in the press as Jackey Jackey), but met a grisly end on Norfolk Island ten years after first arriving in New South Wales. What follows is a concise, summarised account of his life and bushranging career.

William Westwood was born on 7 August, 1820 and was raised in Manuden, Essex; he was the eldest of five siblings. As a youth he fell in with bad company and began acting up. At fourteen he had his first conviction: twelve months hard labour for bailing up a woman on the road and stealing clothes from her. Westwood’s accomplice Ben Jackson got off lightly with a flogging.

When he got out of gaol, Westwood went straight for a time, but was soon in court again as a result of stealing a coat, which he then pawned off. As this was his second conviction he found himself, at the age of sixteen, being transported with 310 other convicts on the convict ship Mangles on 18 March, 1837, for a term of fourteen years. Westwood was a surprisingly refined young man, with a decent education for the time and a strong grasp of language; he conversed freely with anyone he came across. He was described as standing at 5’5″, ruddy complexion, brown hair and grey eyes; a scar on the right side of his upper lip, another on the back of his right hand, a blister mark between the breasts and several tattoos — left arm: illegible blue mark, 7 Aug 1820, 3 Jan 1837; back of left hand: figure of the sun. The tattoos were likely either made while serving time in gaol or while waiting to be transported. Indeed, one of the tattoos was the date he expected to end his sentence and return to England.

When he arrived in New South Wales he was sent to Hyde Park Barracks. He was kept here until given his assignment. He was eventually assigned as a servant to Phillip King at Gidleigh Station, Bungendore. Westwood, now seventeen, endured a harsh journey from Rooty Hill to the place he was to work off his sentence. Days were hard and nights were spent sleeping on bare ground, chained to the axle of the supply wagon. Eventually he arrived at the station to start work, and it was here that he would spent the next three years under overbearing and tyrannical masters. He was always testing the boundaries, and after being spotted in town one night, having sneaked out of his quarters, was dragged back to Gidleigh and given fifty lashes. This only strengthened his resolve to rebel.

After suffering at the hands of his master, who saw fit to have him beaten and whipped at even the slightest offence, as well as being short changed on his already inadequate supplies and rations by the overseer, in 1840 Westwood absconded again. When he was inevitably caught, he was given another fifty lashes and sent to work in an iron gang near Goulburn. Conditions here were even worse than at his first assignment, but he knew it would be fleeting and expected to be sent to a new assignment when he was done.

After his stint in the iron gang was done he was sent back to Gidleigh, much to his dismay. The routine played out again: Westwood absconded, was caught and given fifty lashes. The next time, Westwood wanted to make sure he stayed at large. He and two other convicts gathered enough supplies to last them until they got clear away, then, on 14 December 1840, they bolted.

It wasn’t long before Westwood fell in with the notorious bushranger Paddy Curran. The pair were associated from their time as convicts, and Westwood was eager to have a crack at bushranging. Unbeknownst to Westwood, Curran was extremely violent and his morals were diametrically opposed to Westwood’s in just about every way, but none so conspicuous as his attitude to women. As the story goes, during a house raid, Westwood walked in on Curran in the process of raping the lady of the house. Westwood struck Curran, preventing him from proceeding, and threatened to shoot him. Westwood decided he would rather work alone than associate with such a despicable person.

As Westwood got the hang of highway robbery, news of his daring began to spread through the region, though much of it was pure fiction. On one occasion it was said that he bailed up a commissary and upon discovering the commissary’s wife was in the coach, opened the door, swept the ground with his cabbage tree hat in a gentlemanly manner and invited her to dance with him – a request that she obliged. This and many other anecdotes have no tangible evidence to back them up however. Some accounts attested to his masterful horsemanship, likely honed while he worked as a groom at Gidleigh as part of his assignment. In one story he reputedly bailed up a man in Goulburn and implored him to note the time, then a few hours later he bailed up another gentleman near Braidwood, almost 100 kilometers away, and implored him to do the same in order to set a personal record. Again, this is not likely to be anything other than a flight of fancy. His taste for race horses was nigh on insatiable, with him stealing such creatures from Terrence Murray and several others in the region, either on the roads or from farms. He attributed his success in evading capture to his choice of fine horse flesh over the run down nags the police rode. Among his crimes, he robbed the Queanbeayan mail, and robbed Mr. Edinburgh among several others on the Sydney road. In fact, he took a particular liking to robbing mailmen as the takings were often rather good.

By his own account, there were several close shaves with police, including one where a supposed friend had taken money from him to purchase a Christmas dinner, but had instead procured the constabulary. On another occasion he narrowly avoided capture by hiding in a tree. Westwood had become a fly in the ointment to law enforcement, but it would only escalate.

On the afternoon of Monday 11 January, 1841, Jacky Jacky stole a black mare from Mr. McArthur before attempting to rob a mailman that night at Bungonie, whereupon shots were fired. The next day he raided a store at Boro Creek where he procured fine garments and dressed himself in haute couture so that he may cut a fine figure while about his nefarious deeds, including a rather fetching top hat. Such was the extent of his outrages that the entirety of the mounted police in the region, trackers included, were led by Lieutenant Christie and a Mr. Stewart in hot pursuit.

On 13 January 1841, things came to a head when a man arrived in Bungendore, shouting that he was being chased by a bushranger who meant to shoot him. Sure enough, Jacky Jacky soon arrived on a stolen horse, riding through Bungendore for fully an hour and a half, stopping only to have a chat with a man named Eccleston. Soon word reached the local magistrate, Powell, who went with his brother Frank and a local man named Richard Rutledge to capture the infamous bushranger, despite a distinct lack of weapons with which to defend themselves against the armed bandit. Alas after the posse hesitated in approaching the rogue, he caught wind of them and mounted his steed, riding off at full gallop. The men gave chase. A man named William Balcombe was riding ahead with Revered McGrath in a gig. Stopping the gig in the road, McGrath and Balcombe got out and Balcombe confronted the bushranger, McGrath also pulling a revolver on him. Westwood surrendered, complaining that he could have gotten away if his musket were not in such poor shape.

The desperado was escorted back to the local inn where he was detained. However, Jacky Jacky was not ready to go down without a fight and during the night he overpowered one of his guards and stole his weapons. He bolted out of the inn and across the plains. This did not go unnoticed and Frank Powell saw the fugitive legging it through the open space. Powell fired a pistol at Westwood without effect and gathered more firearms from inside before heading off in hot pursuit with a postman, who had become embroiled in the affair by accident. Soon Jacky Jacky was once more apprehended. But the next day while being escorted to Bargo Brush, Westwood escaped custody on foot. He made it a mile away before being recaptured. Not in the mood for any nonsense, the police tied Westwood to his horse for the remainder of the trip. That night, Westwood broke out of the lock up and stole the guard’s weapon and ammunition before taking a horse and riding to freedom.

The beginning of the end came when he called into the Black Horse Inn on the Berrima Road. Westwood casually walked in and ordered refreshments. He then proceeded to bail the place up. Folklore tells that he was served by Miss Gray, the publican’s daughter, who recognised that this man with pistol braces and fine clothes must be the infamous Jacky Jacky. She screamed and pounced on the bushranger, who fought to throw the girl off as she called for her mother and father. All three tried to restrain Westwood who shook them off time and again until a man named Waters, a carpenter that had been repairing shingles on the inn’s roof, entered and knocked Westwood out cold by striking him on the head with a shingling hammer. In truth it was Grey, the publican, and two assigned servants, Waters and McCrohan, who subdued the bushranger, who took two fierce blows to the head with the shingling hammer to go down. With Westwood captured, the Grays earned themselves a cool £30 reward and Westwood was quickly locked up in Wooloomooloo Gaol.

Westwood was put on trial for robbing the store at Boro and was sentenced to penal servitude for life. He was sent to Darlinghurst Gaol but was shortly caught trying to escape. He was then imprisoned on Cockatoo Island where he organised a party of twenty five other convicts to join him in an escape attempt. Escape from Cockatoo Island was considered impossible, but the impossible was no deterrent for William Westwood. The gang subdued a guard and tied him up. Breaching the boundaries they made it to the water and were about to risk sharks and drowning to swim to Balmain but were deftly captured by the water police. The New South Wales government had had enough of the troublesome Englishman and sent him to fulfill his sentence in Van Diemen’s Land with his co-conspirators. Perhaps Port Arthur could take them down a peg or four.

As the story goes, while being sent to Tasmania, the convict men were put in the brig of the prison ship, naked and shackled in an attempt to prevent any attempts to escape. This of course failed and the men broke free from their cages and tried to reach the deck. Soldiers battened down the hatches and kept things thus until arrival at Port Arthur. When the hatches were opened the prisoners were unconscious in the brig, having been denied food and adequate oxygen due to the captain’s decision not to risk opening the hatches to take food to the men during the several day trip.

Despite Port Arthur’s reputation as an inescapable prison, William Westwood managed to escape from Port Arthur multiple times. Most occasions resulted in a few days of freedom at most. In one attempt at freedom with two other convicts, the trio waded naked into the waters at Eaglehawk Neck. Westwood’s companions were taken by sharks and, in his panic, Westwood managed to lose his clothes after his bundled gear was swept away in the waters as he crossed. He was found days later wandering naked and starving.

Such repeated misbehaving saw him put in solitary confinement for almost three months. When he emerged he was assigned to the commissariat. At this time he helped rescue a boatload of soldiers after their vessel had capsized. His reward was to be sent to Glenorchy Probation Station. Here, as could be anticipated, he once more escaped on 31 July, 1845. This time he successfully took to bushranging with two others. They travelled up through the Tasmanian Midlands in an attempt to reach Launceston, where they planned to steal a boat and sail to Sydney. They became hopelessly lost and were unable to find a boat, resulting in one of the men leaving their company after getting lost, while the other remained until they reached Green Ponds, whereupon he left for fear that Westwood would shoot him as he was the designated guide through the bush and had only succeeded in getting them stranded in unfamiliar territory. When Westwood found himself alone again, he continued on foot towards Launceston, hoping to find a way off the island, but was recaptured before reaching his destination. By this time he was suffering a bout of deep depression and posed no resistance.

Now having exasperated the Van Diemen’s Land government too, he was sentenced to death. The penalty was altered to penal servitude for life on Norfolk Island and Westwood found himself once more sailing to exile, this time headed to what was referred to as the Isle of Despair.

In February of 1844, there was a change of administration at Norfolk Island. Alexander Maconochie, the previous man in charge, had firmly believed in the benefits of rehabilitating offenders rather than simply punishing them, and to this end he reduced work hours, including a work-free Sunday, and created a “marks” system that meant that good behaviour would be rewarded. Flogging incidents were decreased but still strictly enforced in cases of sodomy, which were rampant throughout the prison. Perhaps the most significant measure Maconochie had brought in was vegetable patches. Inmates were given small gardens within which they could grow their own sweet potatoes and other vegetables, and were also given cooking pots and utensils so that they could cook their own meals, allowing them to eat in their cells in privacy. Only able to enact these reforms with the 600 newest inmates, the reforms were still considerably effective, with morale high and major incidents in the prison reduced. Despite Governor Gipps’ recommendations to the government to continue Maconochie’s residency at Norfolk Island, the decision had already been made and Major Joseph Childs became the new Commandant. As a military man with wide campaign experience, and a strict disciplinarian, he decided to institute a few changes to bring the convicts under his thumb. To this end incidents of flogging were increased, hours of labour were also increased, rations were reduced and the small gardens the prisoners were allowed, and the produce they had been growing therein, were banned. In a half-hearted attempt to respond to complaints the administration allowed convicts a cup of peas and a cup of flour every day. Unsurprisingly this was not met with the gratitude that was expected by the administration and Childs set in place a proclamation whereby food was to be served in bulk and individual cooking was prohibited. When the inmates were at work their utensils were confiscated on 1 July, 1846.

This was the final straw and Westwood incited a work party to take up arms against the guards and administration of the island. Approximately 1,600 inmates joined in. Armed with a cudgel, Westwood claimed first blood when he clubbed a particularly despised guard to death. He then took up an axe and headed to the barracks, followed by a seething horde of convicts. Here he entered the kitchen and murdered the cook and upon spying two sleeping soldiers in an adjoining room, used the axe to stave in the skull of one soldier, which alerted the other. The soldier, seeing Westwood before him with the bloodied axe, begged, “Please, think of my wife and children!” to which the unrepentant bushranger replied, “Wife and children be damned.” Westwood then killed the soldier as brutally as the others. Still not satiated, but needing a moment of respite from the mayhem he had caused, Westwood filled a pipe with tobacco and had a smoke while the convicts rampaged around him. Westwood, having had his respite, took up his axe and headed for the commandant’s building. Bursting into the building with an escort, Westwood sought out the commandant. The commandant had secreted himself in a small storeroom adjacent to his office. Westwood tracked him down and took a swing at him, narrowly missing the commandant’s head as he ducked to avoid the blow. Managing to escape, the commandant roused a force of troops that descended upon the marauders and subdued them.

Westwood and thirteen other key figures in the riot, including bushranger Lawrence Kavanagh, formerly of Cash and company, were tried in September and charged with the murders. The evidence was irresistible and twelve of the men were sentenced to execution by hanging.

The morning of his execution, Westwood wrote a letter to the reverend of Port Arthur and also wrote a declaration that he was the only party guilty of the offence that all twelve sentenced men were condemned for. On 13 October, 1846, William Westwood was hanged for his crimes. He was twenty-six years old.

A cast was supposedly made of his face and is the only visual record we have of the dashing young outlaw, despite its contended authenticity. Westwood was buried with the other hanged men in a mass grave called Murderer’s Mound on the boundaries of the prison. Such was the impact of the riots that the commandant was fired from his post and calls were made for the Norfolk Island penal colony to be shut down and the inmates transferred to Port Arthur. In a sense, Westwood has succeeded in bringing about a change in how convicts were treated, though he would not live to see the closure of one of the most brutal and dehumanising prisons in the British Empire.