Britain’s practice of transporting convicts to American colonies was a
fearsome punishment, but not for the chronic criminal James Dalton.
The year was 1721. The ship was called the Prince Royal, its destination the American colonies. And the cake—the cake was gingerbread.
The British crew shouldn’t have been surprised to find the metal file
in the cake. Its stasher, James Dalton—a notorious thief and escape
artist—had been shuttled involuntarily between Britain and America more
times than a trans-Atlantic diplomat. Unluckily for Dalton, this
particular mutiny fell apart as soon as the cake did. Luckily for
Dalton, there would always be a next time. After all, as a convict who’d
been sentenced to the punishment of “transportation” multiple times,
Dalton had mutinied before.
While conditions in 18th-century British prisons could be horrific (more
convicts died in prisons than at the gallows), the most feared
punishment didn’t take place in prison at all. Between 1718 and 1776,
British authorities exiled approximately 50,000 convicts to American
colonies in a policy euphemistically known as “transportation.” Once in
America, the convicts fell under a life of servitude or outright
slavery, underfed and overworked. They had to obey their masters or risk
being imprisoned, with punishment including whippings. In the early
period of transportation, half of these prisoners died while in bondage.
Unsurprisingly, the policy of transportation wasn’t so popular among
British convicts. Some prisoners even begged to be executed rather than
shipped abroad. Thus, plenty of prisoners sentenced to transportation
attempted to escape partway through the journey. Multiple
convict-carrying ships bound for America suffered prisoner rebellions.
Rather than heading to remote parts of the colonies upon arrival, most
escaped convicts preferred to sneak back to Britain, despite being
subject to execution for the meta-crime of returning from
transportation.
James Dalton was one such convict. He grew up surrounded by crime and
punishment; his father cheated in gambling, and his mother and sister
were transported for criminal activity. When Dalton was five years old,
his father was executed for robbery—and in an awkward bit of father-son
bonding, he smuggled young James into the execution site in the cart
that was transporting him to the gallows, so that the boy could watch.
Dalton’s own criminal career started at the age of eleven, and according
to his later prison memoir this involved an impressively diverse range
of misdeeds such as stealing “a parcel of wet Linnen hanging to dry in
the Garden” and toys from a toy shop. He ran a London street gang and
called himself “one of the most impudent irreclaimable Thieves that ever
was in England.” The proceeds from such thefts generally went toward
the company of prostitutes. (Dalton’s inveterate womanizing would also
ultimately land him in hot water.)
Belying the saying about honor among thieves, Dalton stole from his
accomplices, and all testified against each other when caught by the
authorities. After one of his former comrades-in-thieving-and-whoring
gave Dalton up, he was sentenced to the dreaded transportation.
In May 1720, Dalton was put on board the (ironically named) Honour,
bound for Virginia. The felons aboard the ship consisted of 36 men and
20 women. They outnumbered the crew of 12, led by Captain Langley.
Oceanic crossings were prone to severe gusts. “One Day when we were
at Sea,” Dalton would later write, “a Gale of Wind arose that blew very
hard, and carried away our Main-Top-Mast.” Twelve of the men—including
Dalton—agreed to help with the repairs on deck and had their chains
removed. The first mate made Dalton steward of the prisoners. Dalton was
keenly aware of the provisions brought on board by a fellow prisoner,
Hescot: “about fifty Pound of Bisket, two Caggs of Geneva [gin], a
Cheese and some Butter.” Dalton and his prisoner buddies proceeded to
take the food and liquor for themselves. Hescot complained to Captain
Langley, who threatened to whip all of the prisoners to find the
culprit. But before he could do so, Dalton gave the prearranged signal.
He and 14 other felons seized the ship’s weapons, immobilized the 12
crew members, and took control of the vessel.
As mutinies go, it was a relatively civilized one. One prisoner who
had refused to go along with the uprising changed his mind once the
mutiny was complete. Dalton and his co-conspirators granted the turncoat
his freedom in exchange for £10. They even provided him with a receipt.
The mutineers held control for 14 days. Near Cape Finisterre, Spain,
the mutineers relieved the captain and first mate of their watches,
money, and other possessions, amounting to about £100 in value. They
compelled sailors to bring the long boat around. Then the merry
mutineers shared drinks with the captain and first mate before setting
them free. Dalton and his accomplices made off in the long boat and
reached the Spanish coast in just a few hours.
From Spain, the escapees headed to Portugal. Dalton and eight others
boarded a Dutch man-of-war bound for Amsterdam, where Dalton committed
robberies to get back into the swing of things. When he was sufficiently
swung, he returned to England. There, he saved enough money from his
robberies to marry a wheelbarrow pusher named Mary Tomlin.
However, his line of business caused marital discord. Dalton left his
wife to live with another woman—who reported to the authorities that he
had returned from transportation. He was detained and brought to
Newgate prison under the Transportation Act, where he was tried with
other mutineers. All were found guilty and sentenced to death. Their
sentences were later commuted to transportation to America for 14
years.
In August 1721, Dalton set sail with the other passengers of the Prince Royal.
He had rebellion on his mind again, as demonstrated by a gingerbread
cake in his possession that happened to break apart while the convicts
boarded. The guards discovered that there was not just cakey goodness
inside, but also a file—an early version of the cartoon trope of
prisoners breaking out using weapons baked into cakes. Following the
foiling of the filing, the crew tied Dalton up and watched him
carefully.
This time, Dalton made it to the other side of the Atlantic. But he
didn’t stay put for long. Dalton embarked on a cycle of running away,
living on foods such as venison and moss, getting caught, running away
again, selling horses or slaves, making it back to England, and getting
transported—again. While in America, Dalton’s relationships with his
masters were never very conciliatory, likely because of his reluctance
to treat them as masters. At one point, he noted, “when my Master bid me
go to work, I told him Work was intended for Horses and not for
Christians.”
Dalton even took one of these trans-Atlantic trips willingly. When
facing a charge of returning from transportation, he turned informant on
six of his former accomplices to get himself off the hook. While freed,
he lived in fear of retaliation by the widows of the former
accomplices, whose husbands had been hanged based on his testimony.
Thus, using the £40 the government had paid him for his assistance, he
chose to travel to Virginia for a period while things in London cooled
down.
However, he came to the end that befell most convicts who resisted
transportation. Back in Britain, he was put on trial for the highway
robbery of John Waller. Dalton denied committing the crime, though he
admitted to an abundance of others. He considered Waller a liar and a
chronic snitch; Waller was as profuse in testifying against criminal
suspects as Dalton was in relieving people of their property.
Although Dalton swore his innocence to the end, he was reported to be
“very cheerful” on his way to his execution. In 1730, ten years after
he was first sentenced to transportation, Dalton’s body was finally
transported underground—via the hangman’s noose.
Two years later, Waller was convicted of perjury, again for an
accusation of highway robbery. He was pilloried in a public spot. While
he stood bent over with head and hands trapped in the wooden pillory,
his brother Edward beat him to death.
As a criminal, Dalton had nine lives. He essentially bullied his
masters, refused to work, and engineered more felonious exploits in
America. He didn’t die on board multiple ship journeys and he wasn’t
immediately executed upon returning to England.
And he was also clearly successful with the ladies. Dalton was as
prolific a husband as he was a thief; four of his ex-wives came to see
him during one of his stints at Newgate prison, and appeared to be on
good terms with each other. At least one of these marriages was strictly
business, as she was pregnant and her family paid him to marry her.
As for the practice of transportation to America, it ended with the
American Revolution. The pesky Americans’ demands for independence
caused Britain to stop sending its convicts to America and to force them
to Australia instead. The Australian convict trade wound up about three
times as large as the American version.
The smaller scale is just one reason that U.S. history overlooked the
fact that some of its long-lineage East Coasters are presumably
descended from convicts. Patriotic 19th-century historians asserted the
practice was less common than it actually was. Showing that American
politicians’ massaging of facts has a long and illustrious history,
Thomas Jefferson claimed in “Notes on the State of Virginia” that the
number of convicts sent to America as just four percent of the actual
figure, and that these people were thankfully kept out of the American
gene pool: “I do not think the whole number sent would amount to 2000
& being principally men eaten up with disease, they married seldom
& propagated little.”
In Dalton’s case, he certainly stayed true to his path. He achieved a
sort of rascally notoriety toward the end of his life with the
publication of his memoirs, and his family history led a prison chaplain
to later say of Dalton, “One may easily conjecture what Sort of a Tree
grows from such a Stock.” Dalton did little to dissuade anyone, much
less history, of that conjecture.
30, She/her. Used to be DreamingPagan a long time back. Multi-fandom, mostly Black Sails these days but with a lot of Tolkien and funny things interspersed. Complete language and history nerd - be warned. I write fic and occasionally I talk about ships.
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