As far as Europeans are concerned, life in Australia started in earnest when it was turned into a convenient place to dump criminals who would otherwise have been taking up space in British jails and breathing important European air better reserved for respectable citizens. (Never mind the Aboriginals.) So, who were these ne’er‑do‑well Europeans sent to Australia under sentences of transportation? They were some rather bizarre—and ultimately influential—people.
10 George Barrington: Prince Of Pickpockets
Irish‑born George Barrington started down the wrong road when he stabbed a fellow student with a penknife at age 16. After that, he fell in with a group that taught him everything he’d need to know to make a living as a pickpocket and con man.
Able to mingle with the best of them, Barrington headed to London and fell in with the upper class and elite, all the while picking their pockets and stealing whatever wasn’t nailed down. His most notorious crimes included posing as a clergyman and removing the diamonds from the clothing of a member of the Knights of the Garter. His most audacious crime was trying to steal a diamond‑encrusted snuff box (which would be worth several million dollars today) from a Russian count, who’d been given the treasure by Catherine the Great. Barrington was arrested fairly often but managed to either talk himself out of his sentence or get it considerably reduced. In 1790, he finally ended up at the Old Bailey, and even though he reportedly moved the jury to tears, he was sentenced to seven years’ transportation.
He disembarked in Sydney in September 1791 and spent a year laboring on a Toongabbie farm. Apparently having given up his thieving ways, he was given a conditional pardon and, perhaps strangely, was assigned work duty standing guard over crucial supplies for the new government. He was a constable by 1796, but by 1800, his life seemed to have taken another turn. Now declared officially insane, he left his post, was issued a pension, and died four years later.
That’s not quite the end of the story, however. Barrington’s name was attached to some of early British Australia’s finest historical literature. He was credited with writing The History of New South Wales, A Voyage to New South Wales, and even The Impartial and Circumstantial Narrative of the Present State of Botany Bay. The books were massive best sellers, and Barrington’s name was attached to even more publications that proved to be enduringly popular—even though he had nothing to do with actually writing them. After all, who wants to read a dull account of some hot, dusty continent when they could read an exciting, fact‑filled account of a mysterious new land told by one of the world’s finest gentleman pickpockets? A lot of the books’ facts were taken from other, legitimate sources, like journals written by others who had been a part of the First Fleet, and it mostly started with a bookseller named Henry Delahay Symonds. He’s the one who appropriated Barrington’s name and larger‑than‑life past and used it to create the popular image that contemporary British saw of Australia.
9 William ‘Billy’ Blue: The Old Commodore
On February 24, 1829, The Australian ran a column that described what a visitor would see if they were to walk through the streets of Sydney. It highlighted all the sights and scenes, the buildings, the architecture, the shops, the signs of wilderness . . . and the presence of Billy Blue, an elderly man who brought smiles to the faces of all he met.
US‑born William Blue served on the side of the British during the Revolutionary War, earning his freedom from slavery. By the mid‑1790s, he was living in London and laboring as a candymaker. He was convicted of stealing sugar in October 1796. His sentence was seven years’ transportation. After serving more than four of those years on convict ships, he ended up in Sydney.
There, he met and married, worked as an oyster seller and a laborer, and later became a waterfront constable and watchman. Blue was incredibly popular with everyone who knew him and was described as “whimsical.” His home, known as Billy Blue’s Cottage, became something of a landmark, and when he was granted more land, he expanded his business to include the operation of a ferry, which quickly became a fleet of ferries. That gave him the nickname “The Old Commodore,” and it also gave him some other new opportunities. In 1818, he was convicted of smuggling rum. Even though he claimed that he’d simply found the rum floating in the water, he was sentenced to a year in prison, and his titles were taken away.
By the time Blue got out, a couple of others were trying to move in on his ferry service. He appealed to the government for the right to run his ferry, and he won. After his wife’s death, he grew more and more eccentric, often wearing the remnants of an old naval uniform and boarding ships to act as the official welcoming party for those who’d just arrived. He continued to have his issues with the law, once found harboring a fugitive and once barely avoiding prison when he was found guilty of killing a boy who had been tormenting him. Blue had thrown a rock at the boy.
Blue died in 1834, leaving behind a legacy of amusing anecdotes. Several streets in Sydney are named for him, along with his old ferry terminus, which is still in use. Portraits of him still hang in libraries throughout Sydney, solidifying his position as one of Australia’s most eccentric convicts.
8 Isaac Nichols: Postmaster‑Thief
Born in England in 1770, Isaac Nichols had quite a record when it came to breaking the law, and a 1790 conviction for stealing would earn him the popular sentence of seven years’ transportation to New South Wales. When his sentence was served, he was granted some land, where he oversaw some of the convicts serving out their own sentences. Only two years later, he was in court again, this time on the charge of receiving stolen property. Even though he was found guilty, several members of the trial believed that he was innocent and that the evidence against him was perjury. They referred the matter to the higher English court, and a few years later, Nichols was granted a full pardon.
In the meantime, there were some rebellions and reorganizations of the social structure, with Nichols finding himself appointed assistant to the naval officer and a superintendent of public works. It was around 1809 when he decided that he wanted to do something about the mail system—or lack thereof—in Australia. There was little in place to keep people from claiming mail that wasn’t theirs, so Nichols went on to set up the first post office.
Nichols ran the post out of his own house, which was on George Street in Sydney (pictured above). When the mail came in, he’d run the names of all the recipients in The Sydney Gazette, letting them know they’d received something. It was up to them to pick up the mail—and pay him his handling fee of one shilling. Packages cost more, and if the mail was for a person of significant importance, Nichols would deliver it personally. He retired in 1814 and died in 1819. Upon his death, Nichols was remembered by The Gazette not only for his contributions to the realm of public service, but also for the advancements he made in the areas of Australian gardening.
7 Daniel Herbert: Rogue Stonemason
Born in 1802, Daniel Herbert’s crimes were severe enough to earn him a death sentence. In 1827, he was accused and found guilty of highway robbery. Part of what made that crime so particularly severe was the “fear and danger” that went along with it. He’d already been convicted of breaking into a home and stealing, and he and his accomplices pleaded guilty, receiving a death sentence that was later commuted to exile in Australia for life. He was dropped off in Hobart Town in December 1827.
Herbert was assigned to the Engineer’s Department and made frequent appearances before the magistrate for unapproved work absences and drunkenness. In 1835, he was assigned to work on a bridge that’s since become one of the most enigmatic structures from the era. The Ross Bridge in Tasmania was nominated by Engineering Heritage Tasmania as a national landmark, largely because of the ornate carvings that Herbert created. From a distance, it’s a rather unassuming, small bridge, made of three arches that stretch across the river. Up close, each stone is carved with a series of Celtic designs and caricatures, likely of people Herbert knew. Historians have scoured other 17th‑ and 18th‑century architecture for anything comparable, to no avail. Official records make no mention of the carvings; they simply note the bridge’s construction. The keystone is typically the only carved stone, but Herbert’s work on the Ross Bridge remains a striking example of convict artistry.
Engineering Heritage Tasmania suggests that Captain William Turner may have approved the carvings, seeing the project as an opportunity for stonemason convicts to express themselves, reaffirm their humanity, and leave something beautiful behind.
6 Richard Browne: Convict Artist
If you’ve seen any early art depicting Aboriginal peoples, you’ve probably encountered Richard Browne’s work. It’s considered one of the finest examples not only of colonial art but also of how Europeans portrayed the native population.
Browne was born in Dublin in 1771 and was around 40 years old when he was sentenced to exile in Australia. His exact crime isn’t known, but it’s thought to involve forgery. He arrived on Australian shores in 1811 and soon found himself in court again, ultimately being sent to the secondary penal colony in Newcastle. There, he began painting, and his work appeared most famously in a manuscript titled “Select Specimens From Nature of the Birds and Animals of New South Wales,” giving Europeans their first glimpse of the continent’s exotic fauna. A commanding officer in Newcastle recognized Browne’s talent and helped launch his artistic career.
Browne served out his Newcastle sentence and was released in 1817, after which he moved to Sydney and began selling his watercolors. His most sought‑after subjects were Aboriginal people in their natural environments, often depicted with weapons and a caricature‑like quality that reinforced British notions of “civilizing” the natives. His portraits were also used by pseudoscientists of the era, providing visual support for phrenologists who claimed Aboriginals were a lesser species.
5 Zephaniah Williams: Chartist And Coal Baron
In the 1830s, the Chartist movement surged, demanding greater equality for Britain’s working class. Industrialisation in Wales brought cholera, typhus, and hazardous working conditions. By the decade’s end, workers had had enough. On November 4, 1839, an armed uprising at the Westgate Hotel in Monmouthshire left 22 dead and many wounded. At the head of the rebellion were three middle‑class leaders: tailor and ex‑mayor John Frost, actor‑watchmaker William Jones, and geologist‑miner Zephaniah Williams. The trio were found guilty of treason. Though the sentence carried death, they were instead sentenced to transportation, likely to avoid further unrest.
By 1840, the men were in Hobart and Williams was sent to Port Arthur, where he joined a fledgling coal‑mining operation. After a failed escape attempt that earned him 16 weeks of solitary confinement, he developed a method for making iron castings. He later defused a riot at an insane asylum and earned additional freedoms. Following another escape attempt, he returned to coal mining, eventually striking out on his own. He founded the Triumph mine, amassing over 2,000 acres, building camps, tramways, and miners’ homes, and importing workers from England and Wales. Before Williams, coal production in Australia was monopolised, a situation the Chartists had opposed back in Wales. He received a free pardon in 1857 and chose to remain in Tasmania, a fitting end for a man who once faced execution.
4 John Knatchbull: Moral Insanity
A new land offered a fresh start for its justice system, and English‑born John Knatchbull became an unlikely figure in defining legal defenses for murder. Likely born in 1793, he was the son of a man who married three times and fathered roughly twenty children. He joined the navy, retiring without a pension after using it to settle debts. In 1824, under the alias John Fitch, he was arrested and convicted of “stealing with force and arms,” receiving a fourteen‑year transportation sentence that began in 1825.
Knatchbull’s time in the colonies was tumultuous. He earned praise for arresting runaways but was later found guilty of check forgery, receiving a death sentence that was commuted to seven years’ transportation to Norfolk Island. While en route, he acted as a double agent, helping suppress a mutiny that left him partially paralysed and 29 mutineers sentenced to death, with Knatchbull himself named as the chief mutineer.
Returned to Sydney to finish his original sentence, Knatchbull was arrested again in 1844 for murdering an elderly widow, Ellen Jamieson. He confessed, pleading a defence of moral insanity—a claim that he possessed full mental faculties but was morally insane. The court rejected this novel defence, and he was found guilty. He claimed the Devil compelled him, and after a failed appeal concerning the judge’s failure to order his body’s dissection, he was hanged on February 13.
3 Sir Henry Browne Hayes: Fun And Freemasonry
Irish‑born Henry Browne Hayes made several notable contributions to early Australian history, most famously founding the first Masonic lodge on Australian soil. Whether he possessed legitimate authority to do so remains debated, but the meeting he held on May 14, 1803, is widely recognised as the birth of Freemasonry in Australia. He is also remembered for building Vaucluse House, later a national monument and home to W.C. Wentworth. The property, famously snake‑free thanks to turf from Ireland used as a reptile repellent, was acquired by the Australian government in 1910 as a memorial to Wentworth.
Before these achievements, Hayes’s life was a series of bizarre episodes. Originally a captain in the South Cork Militia, he later became a sheriff and was knighted in 1790. By 1797, a widower with children, he resorted to kidnapping a Quaker heiress, Mary Pike, forcing her into marriage. The family intervened, placing a bounty on Hayes. He vanished for three years before surrendering for trial, where he was found guilty and sentenced to death—a sentence later commuted to life transportation to Australia.
Arriving in New South Wales in 1802, Hayes quickly found trouble, harassing the ship’s surgeon and later being linked to a 1804 uprising. After serving his sentence, he was sent to the coal mines of Newcastle. He finally received a pardon in 1809, returned to Ireland in 1812, and died in 1832.
2 Thomas Griffiths Wainewright: Poisoner, Forger, Portrait Painter
Born in 1794 and raised by his grandfather, Thomas Griffiths Wainewright moved in the same circles as William Blake and Mary Wollstonecraft. By the time he married in 1817, he was living beyond his means. An accomplished artist whose work had been exhibited at the Royal Academy, he turned to forging signatures to sustain his lavish lifestyle.
His scheme unraveled when three family members—an uncle, a sister‑in‑law, and a mother‑in‑law—died under suspicious circumstances, each leaving him substantial inheritances. The most incriminating episode involved his wife’s half‑sister, Helen Abercrombie; Wainewright took out an insurance policy on her, and she died shortly thereafter. He fled to France for over five years before being arrested during a 1837 visit to London. Although the court could not directly link him to the deaths, they uncovered his forgery, sufficient to secure a life transportation sentence.
Sent to Van Diemen’s Land (now Tasmania), he first joined a road gang before being transferred to a hospital, where he began painting portraits. His subjects ranged from fellow settlers and pioneers to a lieutenant‑governor and business magnates. Today, his portraits reside in national galleries worldwide, preserving the likenesses of many key figures in Australia’s development. Wainewright’s notoriety extended beyond his crimes; Oscar Wilde and Charles Dickens referenced him as a quintessential villain.
1 Laurence Hynes Halloran: Bigamist Preacher, Public School Founder
The challenge in writing about Laurence Hynes Halloran is deciding where to begin. In 1825, a petition was submitted to the Australian government and all appropriate councils, calling for the establishment of the Public Free Grammar School in Sydney. Authored by Halloran, DD, professor of the classics and mathematics, the petition proclaimed his desire to provide Sydney’s youth with educational opportunities, citing the kindness he’d received in the colony as motivation to give back.
Halloran’s path to Australia was anything but straightforward. An Irish orphan born in 1765, he joined the navy and was first jailed for the stabbing death of a fellow midshipman in 1783. Acquitted the following year, he moved to Exeter, married, and ran a school—likely before any background checks existed. Charged with “immorality” in 1796, he attempted to become an ordained minister but failed. Undeterred, he re‑entered the navy as a chaplain, serving at the Cape of Good Hope. After clashing with the commanding general, he fabricated a series of false claims, was convicted, and sentenced to death—later commuted to life transportation to Australia.
Upon arrival in Sydney, Halloran established his first school. His personal life was turbulent: separated from his first wife, he reunited with another family, including children and a mother who may have been his own niece. He endured numerous defamation suits, financial ruin, and even a prison term for debt. After serving his sentence, he petitioned again for the public school, which opened in November 1825. However, a March 1826 edition of The Sydney Gazette highlighted shortcomings, accusing Halloran of chronic drunkenness, swearing, and student fights. By October, the school’s operation was suspended; Halloran was incarcerated again in November, prompting a restart of the school after his release. He later launched a newspaper—more a personal pamphlet than a true publication—featuring his own articles and reports on his legal battles.
When his newspaper failed, Halloran briefly served as Sydney’s coroner, only to be removed after threatening to publish further articles about an archdeacon. He died in 1831, apparently never learning the lessons he so often preached.