Chiles bought the baseball team Texas Rangers in 1980 and served as chairman of the club until 1989 when he sold the team to group of investors that included the future President of the United States George W. Bush, as well as New York stockbroker Richard Gilder, who later happened to marry Chiles' niece.
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In 1939, after working as a Sales Engineer with Reed Roller Bit Company in Houston, Eddie Chiles founded the Western Company of North America.