John D. Rockefeller
So self-righteous that he claimed, "God gave me my money." The most corrupt mogul of the most corrupt era, he masterminded a grand, cruel conspiracy in 1871 with the railroads to double the price of transporting oil for all producers except his cartel.
Henry Clay Frick
On July 6, 1892, Frick's private militia of 300 Pinkertons fired on a crowd of striking steelworkers and their families. Then he had them evicted from company-owned houses, blacklisted, and tried for murder.
Ford used shadowy henchmen to run "secret police" who spied on employees. He had machine guns, tear gas, and a private army at the ready to deter union organizers. He cheated on his wife with his teenage personal assistant and then had the younger woman marry his chauffeur as a cover.
The man behind the Mouse was a suspicious control freak — a dictatorial boss who underpaid his workers, clashed with labor organizing efforts, made anti-Semitic smears about the other Hollywood studio heads, and wouldn't give due recognition to Mickey's real creator, animator Ub Iwerks, who was supposedly his oldest friend.
He also spied prodigiously for J. Edgar Hoover and cooperated with Senator Joseph McCarthy in the 1960s.
Bribed his way through the oil business. Laundered money for Soviet spies. Forced his mistress to alter the way she looked to throw off his wife. Reneged on promises to support his illegitimate daughter. Forced his board members to give him signed resignation letters that he could accept if they ever dared to oppose him. Then promoted himself for the Nobel Peace Prize.
Perhaps history's most dictatorial accountant, Geneen ran the huge ITT in the 1960s and 1970s. His method: publicly humiliating his top 120 executives every month at grueling, four-day, 14-hour-long meetings that made some of them physically ill. Geneen liked to see the pained expressions on their faces as he tore into them.
People thought Gulf & Western was predatory and acquisitive under Charles Bluhdorn, who earned it the nickname "Engulf & Devour." But when his tough-as-nails protege Davis ascended to the top position, a visitor asked why half of the offices were empty on the top floor of the company's Manhattan skyscraper. "Those were my enemies," Davis said. "I got rid of them."
Scorching and short-tempered, Dick "Nice Guys Finish Last" Snyder ran Simon & Schuster beginning in the 1970s, when the office joke was: What's the difference between the Ayatollah Khomeini and Dick Snyder? Answer: the Iranian mullah took only 52 hostages, while Snyder had 700 — the number of employees at the book publisher.
Scroogelike employer who routinely screamed at his staffers and made them all work the Friday after Thanksgiving, when he called many times to make sure they were still at the office. Proclaimed "Greed is healthy" in a 1986 commencement address at UC Berkeley, the inspiration for the Gordon Gekko speech in Wall Street. Served prison time for securities fraud but reemerged as a tanned La Jolla beach dude — and never said he was sorry.
Her most brilliant business move was having an affair with elderly real-estate baron Harry Helmsley, whom she conned into leaving his wife of 33 years by buying herself an engagement ring — then telling him it was from a rival. Running his hotel empire, she became the "Queen of Mean" to the hundreds of employees she berated and fired on the spot, allegedly for things like a misaligned lampshade. Convinced that taxes were for the "little people," she wound up in prison for evasion.
As CEO of Sunbeam during the late 1990s, Dunlap charged a bulletproof vest and a handgun to his expense account — understandable given the delight he took in laying off thousands of workers and subjecting his executives to profane, abusive tirades. He threw a chair across the room at his head of human resources, allegedly threatened his first wife with guns and knives, and failed to attend the funerals of either of his parents.
Fastow could be so hot-headed that he once got into a punch-out with a taxi driver over 70 cents. Pocket change indeed compared to the $24 million of illicit gains the Enron CFO agreed to give back when he pleaded guilty to securities fraud — or the billions of dollars lost by shareholders when his secret schemes ultimately triggered the company's collapse.
A version of this article appeared in the July 2005 issue of Fast Company magazine.