10 Real-Life Gentleman Criminals

A certain brand of lawbreakers have their own resolute code of morals, act without malice, and possess an air of sophistication that contrasts with ordinary criminals. Fiction is full of these types, such as the famed A. J. Raffles, who plays cricket and detests violence yet sees no problems with his own crimes. Yet these characters also exist outside the pages of books and movies.

10 James Freney

Known as the Irish Robin Hood, James Freney unabashedly stole from the wealthy and helped the poor. Throughout the 1740s, he was a plague on every tax collector and coach that dared travel the roads of Ireland’s County Kilkenny. Still, he did live by his own law: “Rob only those who are worth robbing.”

Like every true gentleman criminal, Freney relied on his wits to avoid capture and insisted his gangs adhere to a thieves’ code of honor, which included remaining courteous, returning goods if they held sentimental value or the victim needed them, and assisting the poor whenever possible. Even so, he was a first-class marksman and never feared getting into a brawl if someone crossed him.

In many ways, the circumstances in Ireland drove Freney, once a pub owner, into a life of crime. At the time, Ireland was suffering under England’s Penal Laws, which intentionally kept the Irish out of a variety of professions. These repressive regulations forced Freney to close down his pub and saddled him with so many taxes that he had little choice but to look outside the law to make ends meet.

This pock-faced, scrappy highwayman became a champion of the common man and committed some of the most daring heists ever to occur in the area—all in five short years. He was captured in 1749 and narrowly escaped going to the gallows when officials realized that in all his exploits he had never killed a single person.

Later, Freney wrote an autobiography of his adventures, modestly omitting all the times he had helped people pay their rent, loaned money, or otherwise supported the poor.

9 William Simon Jacques

The thief William Simon Jacques operated in the genteel world of rare books, manuscripts, and maps. The former accountant and Cambridge graduate has a genius-level IQ. During his days as a bandit, he presented himself as a polite, well-educated man who liked spending his free time in libraries. This innocent, academic persona initially kept folks from realizing he was more interested in stealing books than reading them.

Jacques began pilfering books in the 1990s, around the time he was finishing his degree at Cambridge. The Cambridge Library noticed some of their books went missing, yet they didn’t report the thefts, ashamed at having failed as caretakers of the treasures. Then, in 1996, when two copies of Newton’s Principia Mathematica went missing along with Galileo’s Sidereus Nuncius (worth over $500,000 combined), the library decided it could no longer keep silent.

Still, it took a while for authorities to figure out Jacques was the culprit. He continued to frequent libraries throughout the UK, courteously chatting with desk clerks while squirreling precious books under his tweed coat.

Finally, a library worker caught him in the act, and from there, it didn’t take long for police to pin him as the serial antiquarian book thief. He was jailed in 2002 and spent four years behind bars. Then, upon his release, he picked up right where he left off. He concealed his identity with false names and disguises, winning librarians’ confidences with his intellect. By this point, he had made off with over $1 million in books, and his famous exploits caused the media to dub him the “Tome Raider.”

He managed to slip through the hands of police until July 2010, when he was caught and sentenced to another three and a half years in prison.

8 Elias Whitcomb

Whether Elias Whitcomb was genuinely a man of honor or was just good at playing one is a matter of debate. Unlike the other men on this list, he most likely killed people, as he was an organizer and participant in the deadly 1892 Johnson County War. Despite this, folks said he had a pleasant presence and was an innate gentleman. Today, he is recognized as one of the town fathers of Fort Collins, Colorado, and his name even appears in the Cowboy Hall of Fame.

Whitcomb ran with some of the roughest men in the Old West, including the ferocious “Jack” Slade, who earned a reputation for hanging horse thieves and stage robbers on sight. Among such rough-and-tough company, Whitcomb was considered the moral compass of his posse and often pointed out the good characteristics in what seemed like deplorable men.

During the Johnson County War, he led a vigilante group of wealthy investors and cattlemen against homesteaders rustling cattle from the big ranchers. There’s some argument over whether the ranchers exaggerated the homesteaders’ thievery, and Whitcomb and his men were never prosecuted for their vigilante actions and the resulting deaths. Whitcomb later became a powerful rancher himself and helped start the Agricultural Colony that became Fort Collins.

If Whitcomb wasn’t as gentlemanly as he appeared, perhaps his karma caught up with him in the end. He was killed by lightning in 1915.

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