The Three Strangest CEOs in History

By Lora Keleher , last updated December 22, 2011

Although CEOs are commonly known for eccentricities, the three strangest CEO’s in history are known for engaging in extremely bizarre behavior. These CEOs acted in ways that brought public scrutiny, and garnered media attention.

Al Dunlap
Al Dunlap was known for his predatory and wildly erratic behavior, which came to a head while he was CEO of Sunbeam Corporation. Dunlap earned himself the nickname ‘Chainsaw Al’ for his repeated firing of employees to cut costs and drive up shareholder value. By the time his career was over he’d axed over 18,000 workers.
When he first arrived at Sunbeam as CEO, stock prices doubled and he was credited with rapidly turning around a beleaguered corporation. Wall Street and shareholders celebrated his actions, as he acquired three other companies, and drove stock prices through the roof.
He then pursued an aggressive strategy of taking large orders of discounted merchandise, and posting the profits ahead of the quarter in which the merchandise shipped. Although the strategy of cutting workers coupled with unusual accounting practices inflated stock prices and netted him over 100 million dollars in the short term, his methods ultimately failed in the long run. As pressure increased because of media attacks and his inability to maintain high profit levels, his behavior grew increasingly strange and he began coming up with bizarre conspiracy theories involving prominent individuals in company. When the board eventually fired him from Sunbeam, even his family celebrated his demise.
Harold Geneen
Harold Geneen, CEO of ITT, was known for building ITT from a small company into a large multinational conglomerate. He was a notorious workaholic, who began his career at sixteen working for the New York Stock exchange. He was known as one of the most controversial CEO ‘s of the 1960’s and 1970’s because he built his career by purchasing companies across all different markets from car rental businesses to construction companies to bakeries. He was involved in trying to block a Chilean candidate’s election, and for supposedly bribing the Republican Party into settling an antitrust lawsuit in his favor. Despite constant media scrutiny, Geneen never backed down from his business strategies and worked until the day he died.
Howard Hughes Jr.
At the tender age of eighteen, Howard Hughes Jr. father died, and at twenty-one, Hughes Jr. took the reins of the company his father built. He went on to finance major motion pictures including “Scarface” and “Hell’s Angels.”
Throughout the years he designed a women’s half-cup bra, earned his pilot’s license, and had a brief stint as an airline pilot. Hughes also owned movie studio RKO, built the Texas Theater, and founded the Hughes Aircraft Company.
Over time his shadier dealings surfaced, and he became known for his role in politics and political scandals involving both the CIA and organized crime. He was involved in a plot to assassinate Castro, Nixon’s Watergate scandal, and the defamation of the Kennedys. When the media publicized his activities, he became increasingly controlling and reclusive, making it nearly impossible for even longtime allies to communicate with him. He died with a fortune worth over two-billion-dollars.
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