Obscure Operators of Wikipedia

James Wilkinson was a Continental Army officer who was twice compelled to resign, twice served as senior officer of the United States Army, and was secretly paid by Spain for nearly 20 years while commanding American troops. He sabotaged his commanding officer Anthony Wayne by writing anonymous attacks to newspapers, urging contractors not to perform, and tipping off the Spanish to American military plans; Wayne died of a stomach ulcer before he could court-martial Wilkinson, who then replaced him. He conspired with Aaron Burr, testified against him at trial with obviously forged documents, was court-martialed and exonerated multiple times, and died in Mexico City while seeking a land grant; Theodore Roosevelt later called him "the most despicable character" in American history.

John Goodman inherited his father's air conditioning company, built it into the largest privately held manufacturer in the United States, and sold it for $1.43 billion in 2004. He founded the International Polo Club Palm Beach to attract South American players and wealthy individuals from Miami, then ran a stop sign near the club at 1 AM with a blood alcohol level more than twice the legal limit, fled the scene without calling for help, and left a 23-year-old to drown in a canal. He testified that his car malfunctioned and denied being drunk, was convicted of DUI manslaughter, sentenced to 16 years, and is currently incarcerated with a 2028 release date.

William Trickett Smith was the chairman of the Dauphin County (PA) Republican Committee who was disbarred and imprisoned for bid rigging in 1985, then convicted of theft, arson, and insurance fraud while stealing from his clients' estates. He was the main prosecution witness in the trial of Pennsylvania Treasurer Budd Dwyer, who shot himself on live television the day before sentencing; Smith later admitted on camera that he had lied under oath about offering Dwyer a bribe. His son murdered and dismembered his wife in Peru, and Smith was sentenced again for filing a false criminal complaint in an attempt to have his son temporarily extradited so he could escape.

William Paterson was a Scottish trader who spent time in the Bahamas dealing with buccaneers, made his fortune in the slave trade, and co-founded the Bank of England in 1694. He tried to convince England, the Holy Roman Empire, the Dutch Republic, and Brandenburg to establish a colony in Panama; all refused, so he persuaded the Scottish government to undertake what became the catastrophic Darien scheme. He accompanied the expedition in 1698, his wife and child died there, he became seriously ill, and Scotland ended up in such financial ruin that it joined England to create Great Britain.

Sam Maceo was a Sicilian immigrant who moved to Galveston, started bootlegging out of his barbershop, allied with a local gang leader, and built an empire of casinos, speakeasies, and brothels that controlled both the government and organized crime in the city for 30 years. Al Capone sent Frank Nitti to invest in Galveston operations; Maceo's men chased him out of town but partnered with them on bootlegging and secured financing from one of Galveston's most prominent families through their insurance company. He was never allowed to join the local country club, organized a fundraiser with Frank Sinatra and Jack Benny after the Texas City explosion, and invested heavily in the Desert Inn just before his death.

Sam Ward was a New York banker's son who married into the Astor family, lost his wife and newborn within days of each other, collapsed his family's banking firm through speculation, joined the '49ers and made and lost a fortune in San Francisco. He moved to DC as a secret lobbyist for Paraguay and invented social lobbying by throwing dinner parties for his clients with congressman during the Gilded Age. A man he had nursed back to health in the gold fields became a stock manipulator and gave him $750,000 in profits; Ward lost it backing a Long Island resort, fled to Europe to escape creditors, and died near Naples.

Palle Huld was a 15-year-old Danish Boy Scout working as a clerk at a car dealership when he won a newspaper competition to circumnavigate the globe unaccompanied in under 46 days, using any transport except aviation. He left Copenhagen on March 1, 1928, traveled through Britain, Canada, Japan, Korea, Manchuria, the Soviet Union, Poland, and Germany, and returned 44 days later to a crowd of 20,000. His journey reportedly inspired Hergé to create Tintin; he went on to appear in 40 films and died at 98.

Kirksey Nix was the boss of the Dixie Mafia who began serving life without parole in 1972 for murdering a New Orleans grocery executive, then built a criminal empire from inside Angola prison by placing personal ads in gay magazines and convincing the men who responded to wire money. He made hundreds of thousands of dollars from the scam, kept it in a trust account maintained by a Biloxi attorney, and when $100,000 went missing he arranged to have the attorney's former law partner, a circuit court judge, and the judge's wife murdered. Son of a longtime Oklahoma state judge, he is currently incarcerated at a federal prison in Oklahoma.

Whitney Walton was a Baton Rouge social worker who spent the 1970s and 1980s calling famous men as "Miranda Grosvenor," a fictitious blonde Tulane student, and enchanting them so thoroughly with late-night phone conversations that Quincy Jones and Richard Perry proposed marriage. Billy Joel wrote songs and sang them on her answering machine, considered her at times his "only friend," and thought about writing a musical about her; Warren Beatty, Bob Dylan, Robert De Niro, Bono, and Ted Kennedy were among the others who rearranged their evenings to talk to her. HarperCollins paid nearly $1 million for her memoir, De Niro bought the film rights, and the book was cancelled without explanation.

John Bloom was a British entrepreneur who started his first business as a soldier by undercutting the RAF's contracted coach company, won the lawsuit, and adopted the motto "it's no sin to make a profit." He sold Dutch washing machines door-to-door at half the retail price, captured 10% of the British market, went public, and became the UK's largest press advertiser, then lost his financing in an 11-week postal strike and went into liquidation. David Bowie credited him with arranging his first record deal at a Park Lane party and he spent his later years running medieval-themed restaurants and a piano bar in Mallorca.

Jackson Stephens grew up on a farm in south Arkansas during the Depression, met Jimmy Carter at the Naval Academy, and joined the investment house his brother had started in 1933, building it into one of the biggest institutional shareholders in Walmart, Tyson Foods, and Alltel. He underwrote the initial public offering for Walmart in 1970, launched a data processing company that sold for hundreds of millions, and formed a Hong Kong venture with Indonesian banker Mochtar Riady. He chaired Augusta National for seven years, became a key financial backer of Bill Clinton's 1992 presidential campaign, and gave away tens of millions to Arkansas schools and hospitals.

William Bulger grew up in a South Boston housing project, served the longest tenure as president of the Massachusetts Senate in history, and became president of the University of Massachusetts despite having no academic doctoral degree or experience in higher education. His older brother Whitey led the Winter Hill Gang and was convicted of 11 murders; William lived next door to a house where the gang stored weapons and committed at least one killing, took a secret phone call from Whitey two weeks after he became a fugitive, and told a grand jury he hoped he would never be helpful to anyone trying to catch him. When the Unabomber's brother turned him in, William Bulger was asked if he would ever do the same; he sat for several moments, unable to speak.

Darla Moore grew up on a cotton farm in Lake City, South Carolina, became the highest-paid woman in finance by specializing in bankruptcy takeovers, and was put on the cover of Fortune as "The Toughest Babe in Business." She removed T. Boone Pickens from his own company after he ran it into trouble, fired future Florida Governor Rick Scott from Columbia/HCA when a Medicare scandal broke, and married Richard Rainwater, whose net worth nearly tripled during their marriage. She gave $70 million to the University of South Carolina business school, $25 million to convert an old Walmart in her hometown into an education center, and in 2012 became one of the first two women admitted to Augusta National alongside Condoleezza Rice.

Billy Walters grew up in rural Kentucky with no running water, got a $40 bank loan at age seven to start a lawn-mowing business, once lost his house in a game of pitching pennies, and became the most successful sports bettor in American history with a 30-year winning streak. He noticed a biased roulette wheel at the Golden Nugget, won $3.8 million in 38 hours, then built a computer analysis operation that made him $50 to $60 million in good years betting on football and basketball. He was convicted of insider trading after a Dean Foods board member fed him tips using a prepaid cell phone, served time until Trump commuted his sentence, and wrote a memoir accusing Phil Mickelson of cowardice for not testifying on his behalf.

Sam Zemurray was a Jewish immigrant from Russia who arrived in Alabama at 14, started buying overripe bananas at the Mobile docks for quick resale, and had $100,000 by 21. When the State Department told him not to meddle in Honduras, he hired a mercenary army in New Orleans, sailed down on a decommissioned Navy ship, overthrew the president, and got tax concessions from his replacement. He sold his company to United Fruit for $31.5 million before the Great Depression, bought a controlling share in a hostile takeover when its price collapsed 90%, walked into a board meeting with the proxies, and said, "You've been fucking up this business long enough."

Thomas Friedkin inherited a major stake in Pacific Southwest Airlines when his parents died, kept working as a pilot while sitting on the board, but got only $3.4 million when it sold for $400 million. His friend Carroll Shelby turned down an offer to become a Toyota distributor because Lee Iacocca told him American carmakers would "push the Japanese back into the ocean," so Shelby introduced Friedkin instead and Friedkin built Gulf States Toyota into a $5.7 billion company. He owned a MiG-15 and a P-47 Thunderbolt, insisted on flying his own Corsair in the 1970s show Baa Baa Black Sheep, played Miner Tom in Pale Rider, and founded a safari company in Tanzania to fund conservation of 3.2 million acres.

William Clark Falkner was a Mississippi novelist, Confederate colonel, and railroad founder. He killed a man with a bowie knife, led a regiment at the First Battle of Bull Run, wrote a steamboat murder mystery that sold 160,000 copies, and was shot dead by a former business partner the day after winning election to the state legislature. His great-grandson William Faulkner added a "u" to the family name, won the Nobel Prize, and used him as the model for Colonel John Sartoris in Yoknapatawpha County.

Edward Orange Wildman Whitehouse was an English surgeon and amateur electrician who talked his way into becoming chief electrician for the first transatlantic telegraph cable. The cable opened in 1858 and Whitehouse sent the first messages, but when signals declined he delivered massive shocks of 10,000 to 15,000 volts to fix the problem and destroyed it after three weeks. He blamed everyone else, was found responsible by an 1861 inquiry, and returned to his surgical practice in Brighton.

Collis Huntington was a teenage peddler who became a Sacramento hardware merchant, pooled resources with three other businessmen to build the western half of the transcontinental railroad, and spent decades in Washington bribing congressmen. His private letters were exposed in 1883 litigation and made him one of the most hated railroad men in America, with detailed descriptions of payoffs and his eagerness to use money on politicians. He founded Newport News Shipbuilding and built the city of Huntington, West Virginia.

Hungry Joe Lewis was a 19th-century bunco man who swindled a general, a judge, and Oscar Wilde, and to whom an 1885 biography attributes the phrase "There's a sucker born every minute." He befriended his marks over dinner at fine hotels, lured them into rigged card games, and once convinced a congressman that he was a banker's son so convincingly that when the real son arrived, the congressman threw him out. He served time in Sing Sing and the Maryland State Penitentiary, emerged to work as a cigar vendor in the Bowery, and was buried under a false name.