George Steinbrenner, 1930–2010

Throughout a tempestuous 37-year reign as chief owner of the New York Yankees, no one ever doubted George Steinbrenner’s desire to win. “Winning is the most important thing in my life, after breathing,” said Steinbrenner, whose teams amassed seven World Series championships during his tenure. “Breathing first, winning next.” But Steinbrenner’s hotheaded ways—he notoriously hired and fired manager Billy Martin five times in 14 years—also produced endless clubhouse drama and a reputation for boorishness bordering on tyranny.

George Michael Steinbrenner III was born in Rocky River, Ohio, where he grew up seeking to please his domineering father, who ran the family shipbuilding business. “Steinbrenner often told of how his father approached him after one of his childhood track meets,” said the Los Angeles Times, “not to congratulate him on winning two events but to scold him for losing a third.” At 14, he entered Culver Military Academy in Indiana. When MIT, his father’s alma mater, declined to admit him, he studied literature at Williams College, where he wrote his senior thesis on Thomas Hardy. After college, Steinbrenner became an assistant football coach at Purdue and Northwestern.

In 1957, Steinbrenner’s father ordered him to join the family business, said The Washington Post. “I wish I could have stayed in coaching,” he later recalled. He soon merged the business with American Ship Building Co., eventually tripling its revenue. With his growing wealth, Steinbrenner began dabbling in professional sports, investing in an American Basketball League franchise and later taking a 7 percent stake in the Chicago Bulls, which he subsequently sold. But it was his role as head of a syndicate that bought the Yankees for $10 million, in 1973, that established Steinbrenner as “the best known and most disliked owner in professional sports.”

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After first promising to be a hands-off owner—“I’ll stick to building ships,” he said—Steinbrenner “emerged as one of the most powerful, influential, and, in the eyes of many, notorious executives in sports,” said The New York Times. He changed managers 20 times in his first 23 seasons, leading some to nickname the franchise the “Bronx Zoo,” and he appeared on the cover of Sports Illustrated costumed as Napoleon. When free agency came to baseball in the 1970s, Steinbrenner opened the floodgates to multimillion-dollar contracts, spending lavishly to obtain pitcher Catfish Hunter and slugger Reggie Jackson. By 2009, with stars like Derek Jeter and Alex Rodriguez on board, the Yankees’ $210 million payroll “dwarfed all others in baseball,” confirming to many that the organization had become an “evil empire.”

Steinbrenner’s excesses went beyond profligate spending on the team, said the New York Post. In 1974, he was indicted on 14 criminal counts involving President Nixon’s re-election campaign, and pleaded guilty to obstruction of justice and making illegal campaign contributions. (He was later pardoned by President Reagan.) In 1990, “it was learned he had paid a known gambler for damaging information on slugger Dave Winfield, in hopes of blackmailing the former Yankees star into dropping a lawsuit against the team.” As a result, Steinbrenner was banned from baseball for life, though his banishment was lifted in 1993.

Despite a tumultuous tenure, Steinbrenner, known widely as “the Boss,” took a faded team in a down-on-its-luck New York City, and helped restore both to glory, bringing star players and glittering championships back to the Bronx. Along the way, he transformed a $10 million investment into the most valuable franchise in sports, with an estimated value of $1.6 billion, a brand renowned worldwide, and a new stadium next to the original “house that Ruth built.” It really wasn’t that complicated, he once explained: “I hate to lose—hate, hate, hate to lose.”