George Steinbrenner

Born Rocky River, Ohio

Under George Steinbrenner’s thirty-seven-year tenure as owner of the New York Yankees, the team flourished, winning seven world championships and eleven pennants. Despite that success, Steinbrenner was a controversial figure because his brash and sometimes illegal behavior consistently put him in the headlines, even over the achievements of his team and players. Heir to a Great Lakes shipping company, Steinbrenner acquired the Yankees in 1973 and quickly demonstrated an inability to distance himself from the team’s daily business, earning himself the nickname “The Boss.” The Yankees underwent nineteen managerial changes during his ownership, just one illustration of his hands-on style.

David Levine’s caricature humorously points out both Steinbrenner’s inability to remain unobtrusive as well as his shady money dealings, with a bag of money weighing down the bat he is holding.