10 of the Biggest Scoundrels in American History

America has produced an amazing gallery of nefarious characters over the past three centuries--from brutal serial killers to crafty con men, counterfeiters, and snake oil salesmen.
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America has produced an amazing gallery of nefarious characters over the past three centuries--from brutal serial killers to crafty con men, counterfeiters, and snake oil salesmen. In my new book, Villains, Scoundrels, and Rogues: Incredible True Tales of Mischief and Mayhem (Prometheus Books, $18.95), I profile thirty of the country's most memorable ne'er-do-wells. Here are ten of our absolutely slipperiest specimens ever.

1. Daniel Drew—Wall Street Pirate
Library of Congress
From the 1840s to the 1870s, Daniel Drew was one of America’s most ruthless financiers—a man who believed that speculating on Wall Street without insider knowledge was like “buying cows by candlelight.” During the Civil War, he scalped the public in collusion with New York’s infamous Boss Tweed. Drew made a chunk of his fortune by manipulating New York & Erie Railroad stock, but his association with swindlers Jay Gould and Jim Fisk cost him dearly. Once worth $13 million ($194 million today), old “Uncle Daniel” died with an estate of $148.22.
2. & 3. Maggie and Kate Fox—Phony Mediums
Missouri History Museum, St. Louis
In 1848, Maggie, left, and Kate Fox played a joke on their mother by pretending to communicate with the spirit of a dead peddler in their family’s farmhouse in Hydesville, New York. The sisters’ prank—accomplished by cracking their knuckles and toe joints—led to their becoming the most famous mediums in the country and gave birth to the international movement known as Spiritualism, whose adherents, once numbering in the millions, believe in the possibility of communicating with the dead. Although the Fox sisters eventually admitted to their fakery, Spiritualism lived on.
4. John Parker—Irresponsible Cop
Library of Congress
Washington policeman John Parker abandoned his guard post at Ford’s Theatre, left, on the evening of April 14, 1865, allowing assassin John Wilkes Booth unchallenged access to President Lincoln. Unable to see the stage from where he sat—in the narrow passageway behind the President’s box—Parker moved so he could enjoy the play, Our American Cousin. During intermission, he went for drinks in the saloon next door and never returned to his post. Parker had previously been hauled before the police board over a dozen times for conduct unbecoming an officer.
5. Hetty Green—Tax-Dodging Miser
Library of Congress
In the late nineteenth century, investor Hetty Green lived like a wretched pauper, despite having become the first woman to earn a fortune on Wall Street. The multimillionaire was so miserly that she once dressed her son in rags in an attempt to obtain free medical treatment. To avoid establishing a permanent residence and having to pay state taxes, she moved from one flophouse to another in New York and New Jersey. Her brazen tax dodging helped spur the passage of a federal income tax in 1894 and a federal estate tax passed two months after her death in 1916.
6. Joseph Weil—Confidence Man
Nabat/AK Press
Chicago con artist Joseph Weil had a talent for separating the gullible from their money while using a variety of assumed identities. From the 1890s to the 1940s, the “Yellow Kid” passed himself off as a stockbroker, banker, physician, mining engineer, chemist, geologist, and land developer. Weil originated or perfected numerous cons, including the phony bookie operation portrayed in the movie The Sting. Claiming that “you can’t cheat an honest man,” Weil said his victims “all wanted something for nothing.” Instead, he gave them “nothing for something.”
7. Peggy Hopkins Joyce—Gold Digger
Library of Congress
A minor actress in the 1920s and ’30s, Peggy Hopkins Joyce reputedly inspired the rich-husband-stalking character Lorelie Lee in Gentlemen Prefer Blondes. The most celebrated of Joyce’s six marriages were calculated liaisons that vaulted this woman of humble birth into high society. During her brief union with wealthy lumberman James Stanley Joyce, she wrangled $1.4 million ($17 million today) in jewelry and other gifts—while cuckolding her husband with at least nine lovers. She admitted to her gold digging without apology, saying, “It is better to be mercenary than miserable.”
8. John Brinkley—Medical Fraud
Library of Congress
From 1917 through the 1930s, physician John Brinkley made millions by implanting goat testicles in men to restore their virility. Fifty new patients a week traveled to Brinkley’s clinic in Milford, Kansas, eager to pay $750 for the unsafe and medically useless operation. The placebo effect often convinced Brinkley’s patients that their potency had been restored, and Brinkley increased his odds of success by announcing that the operation worked best for the intelligent. The goat gland doctor’s luck eventually ran its course. He died in bankruptcy after being exposed as a quack.
9. Samuel Dickstein—Congressman–Spy
Library of Congress
In the years prior to and during World War II, New York congressman Samuel Dickstein kept watch on the subversive efforts of Nazi supporters in the U.S. He also bolstered his income from 1937 to 1940 as a bumbling Soviet spy. Code-named “Crook” because of his persistent demands for money, Dickstein fed his handlers newspaper articles and public government reports—“rubbish,” the Russians called it. Dickstein’s congressional endeavors led to the creation of the House Un-American Activities Committee, an investigative body that would trample individual rights.
10. Don Lapre—Infomercial Huckster
New Strategies
Starting in the early 1990s, shrieking pitchman Don Lapre made and lost fortunes peddling questionable self-help products on late-night TV. His biggest profits came from selling add-on services to those who set up 1-900 numbers or websites through his company. His empire came tumbling down in 2011 when he was indicted for fraud over his Greatest Vitamin in the World business, charges that led to his suicide. Selling online distributorships for $35, along with endless marketing products, Lapre had raked in $52 million in three years but paid out a pittance in commissions.
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