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What can be said of a criminal mastermind? I’d always been deterred from a life of misdeeds by my utter conviction that I’d be lousy at it, and that the inevitable consequences of such a career are either prison, demise by the hand of the swarthy hero, or if one is lucky, a paranoid, skittish retirement. With my luck, I’d be foiled by some cartoonish gaggle of meddling kids and their talking stoner-dog.

Some of history’s most capable crooks have piqued my interest throughout this project, more out of my fascination at the tenacious longevity and the sometimes-cinematic flair with which they’d plied their trade. While I don’t aspire to join their ranks, I do envy how they have crafted their own good fortune.

The key here is that the criminals about whom I’ve written are famous – or at minimum, famous enough to warrant at least a brief Wikipedia page. But shouldn’t the truly successful master-crooks still be anonymous to us, even after the final curtain of death has ushered them off the mortal stage? Perhaps. But I believe a case can be made for the exquisite professionalism and enduring evil genius of those bad guys whose names nonetheless appear in print – even those who have risen to become legends. Take, for instance, the near-perfect vocational aptitude of the 19th-century criminal genius, Adam Worth.

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Adam turned to a life of crime as soon as he’d been kicked off the grid. Raised in Cambridge, Massachusetts, Adam ran away from home at ten, then at seventeen he lied about his age so he could join the Union Army to fight in the Civil War. After getting wounded at the Second Battle of Bull Run, Adam learned he’d been listed as Killed In Action by accident. He took advantage of his premature death and disappeared.

He found easy work as a bounty jumper; he’d be paid off by citizens to sign up for the army in their name, then after he’d collected his army paycheck he’d flit back to the shadows. Adam pulled this off several times, never getting caught, though he did attract some attention. Local law enforcement was in no position to help out the armed forces, but a new type of heroic protagonist had emerged on the scene in the form of Allan Pinkerton and the Pinkerton National Detective Agency. Pinkerton’s was the first private investigation firm in American history, and they were happy to chase after Adam Worth and the other bounty jumping scum who were profiting from military desertion.

Curiously, Pinkerton PI went for the exact opposite of Magnum PI's swarthy mustache.

Curiously, Pinkerton PI went for the exact opposite of Magnum PI’s swarthy mustache.

The war ended, and Adam settled into the pickpocket business in New York. He was an entrepreneur, however, soon acquiring his own gang of pickpockets, and working his way up to little robberies and heists. Well-known criminal fence Marm Mandelbaum took Adam under her wing, helping him plan more elaborate capers. At Mendelbaum’s request, Adam helped to tunnel under the soil outside the White Plains jail in order to liberate safecracker Charley Bullard. Charley and Adam became close friends and partners in their nefarious deeds.

In 1870, Adam and Charley moved to Liverpool after having robbed the Boylston National Bank back in Boston. Once again, the Pinkerton agency was enlisted to investigate, and Adam and Charley felt an ocean could provide enough of a buffer between themselves and the heat to allow them to continue stealing in peace. They adopted pseudonyms (Adam was financier Henry J. Raymond) and reignited their criminal empire across England.

That’s when she walked in.

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Kitty Flynn was a barmaid in London, and she won over both men with her charm. Charley won her hand, though it’s rumored that Adam won her loins, in that the two girls Kitty produced within her marriage to Charley were alleged to be Adam’s doing. The trio became a tight-knit team, moving to Paris and opening a genuine American saloon, complete with an upstairs gambling hall that was rigged to fold into the walls and floors in case of a raid. It was here that Allan Pinkerton, head of the detective agency that had scrambled deep in Adam Worth’s dust back in America, wandered in and recognized the three criminals.

But it was the Paris police’s continuous raids on the joint that prompted the three criminals to return to London and resume their British crime ring. Bad checks, diamond heists, swindles, thefts and all sorts of rackets padded their pockets. Scotland Yard knew who they were, but as much as Inspector John Shore made it his mission to bring this gang to their knees, there was no solid evidence. Even when Adam personally stole a valuable Thomas Gainsborough painting from a London gallery, it was never traced to him – likely because he never tried to sell it. He just wanted it for himself.

He really liked gigantic hats.

He really liked gigantic hats.

In the 1880s, Adam married a woman and had two kids of his own – all under the pseudonym of Henry J. Raymond. It’s not known if his family had any idea of his true identity. In 1892, Adam visited a Belgium jail where Charley Bullard was being held. Charley’s alcoholism had fuelled a violent streak, and he and Kitty had left London a while earlier, following his whim. When Adam got there, he learned that his friend had recently died.

Working with a ridiculously green crew, Adam orchestrated a haphazard robbery of a money delivery cart in Liège, Belgium. The robbery was completely bungled, and Adam found himself on trial. Scotland Yard and the NYPD supplied all the info they could, in hopes that Adam would be locked away for eons. The Pinkerton Detective Agency was contacted, but they kept quiet. Kitty Flynn reached out to Adam and offered to finance his legal defense. The trial was elaborate, but Adam maintained that this robbery was his one dalliance on the grisly side of the law. Ultimately, that was all they could make stick. Adam got seven years behind bars.

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When Adam was released for good behavior in 1897, his wife had gone mad with grief and was locked in an asylum, while his kids were off in America being raised by relatives. Adam swiped £4000 from a London diamond shop, then sped to New York to reunite with his kids. He tracked down William Pinkerton, who now ran his father’s agency, and spilled his entire life story. None of it was admissible in court, but the truth was finally out there, off his chest. Adam arranged for the return of his beloved painting of Georgiana, Duchess of Devonshire in exchange for $25,000, then returned to London with his kids to live out the rest of his life in peace.

Where Adam Worth found eternity was through the works of Sir Arthur Conan Doyle. In an effort to kill off Sherlock Holmes, Doyle fashioned the character of Professor Moriarty, whom he described as the “Napoleon of crime” – a title that Scotland Yard had assigned to Adam years earlier. Moriarty only appeared in two Sherlock Holmes stories, though in subsequent cinematic retellings he has been elevated to the status of Holmes’ equal, and his most incendiary arch-nemesis.

That seems like a fair legacy to bestow upon a man who – apart from one lousy slip-up in Belgium – had nearly led the life of the most masterful criminal mastermind. Adam passed away in 1902, his contribution to the lore of lecherousness complete. In a twist that can only be described as literary in nature, his son grew up to find employment on the sunnier side of the law. For the Pinkerton Detective Agency.