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George Steinbrenner: a leader loved & hated

George Steinbrenner, the late owner of the New York Yankees, was a deeply-flawed leader, who achieved incredible results

Steinbrenner purchased the Yankees in 1973, when he and a group of investors acquired the team from CBS for $10 million. He successfully took a great, but struggling franchise and transformed it into a billion-dollar global enterprise. Under his stewardship, the Yankees won 11 American League pennants and 7 World Series titles.

Steinbrenner exhibited some leadership traits that could be labeled reptilian, meaning that he was tough and cold-blooded when it came to winning. The Boss’s focus on results and desire to win was consuming. He could not help himself from micromanaging, and his child-like temper tantrums were famous. He often criticized his players in the press and he often became entangled in controversies large and small. He once fired a secretary for forgetting his tuna fish sandwich. He was indicted on 14 criminal counts for making illegal contributions to President Richard Nixon’s campaign in the early 1970’s. He was suspended from baseball in the early 1990’s after paying a small-time gambler to dig up information intended to smear his own player Dave Winfield. He had a particularly contentious relationship with Billy Martin, whom he hired and fired 5 different times. Steinbrenner alienated Yogi Berra to such an extent that the Yankee great refused to set foot in the Stadium for over a decade.

Off the field, Steinbrenner also exhibited leadership that could be labeled mammalian, meaning that he also had a warm and nurturing side. So before you scapegoat George keep the following in mind: he was an incredibly charitable man.

  • Before he was prominent, George helped start the Junior Olympics in Cleveland, which helps boys and girls compete in track in order to stay out of trouble. He also personally offered many athletes, like John LeCourt, college scholarships.
  • He started the Silver Shield Foundation, which pays college tuition for all children whose fathers died in the line of duty as police officers or firefighters in New York State and in Hillsborough County, Florida. Hundreds of youngsters have received college educations as a result.
  • For years, George funded the Whitey M. Young Classic, a football game at Yankee Stadium between Grambling College and another historically black college. In 1974 when Yankee stadium was being refurbished, Grambling’s coach, Eddie Robinson, had no place to play. Steinbrenner agreed to cover all expenses for the game, which continued for many years thereafter.

Many people, who often started out as strangers to George Steinbrenner, owe him a lot.

  • When George heard in 1988 about a twenty-year old construction worker who was killed by a stray bullet during a nearby argument over a drug deal, he paid for the man’s funeral.
  • In 2006, Steinbrenner read about a thirteen-year-old Arkansas boy who gave a thousand dollars he had earned working to his debt-ridden middle school rather than use it to travel to New York on vacation. George made the boy a special guest of the Yankees on Old-Timers’ Day. He flew him on an all-expense paid trip to New York and sent him a $1,000 check.
  • George paid for the funerals of four children who died in their home in the Bronx when their space heater sparked a fire.
  • In 1973, an eighteen-year-old Ray Negron went with his half-brothers and cousins to illegally graffiti a wall of Yankee Stadium. Ray, a gentle kid who sported a tall afro, had begun spray-painting a big “NY” on the wall of the stadium when a black limousine pulled up. Everyone saw a large man get out of the limo, except Ray. Before he could run, George grabbed Ray by the scruff of the neck and marched him into the stadium’s holding cell. After leaving the terrified boy in the cell for ten minutes, George took Ray into the Yankees locker room and ordered the clubhouse manager to give him a uniform. “He’s got damages he’s got to work off,” said Steinbrenner, who made him a bat boy for a couple of days. When one of the regular boys got sick, Negron stayed on and never left. He has been a Yankees employee on and off ever since. Over the next 30 plus years he held many roles in the organization, including working in the audiovisual department and being a drug counselor to Dwight Gooden and Darryl Strawberry. In 2006, with George’s blessing, he published a children’s book, The Boy of Steel, about a young cancer patient, Babe Ruth, and the Yankees.

Sources: Golenbock, Peter (2009). George. John Wiley & Sons, Inc.: Hoboken, NJ.

George Steinbrenner leaves behind numerous leadership lessons, good and bad. I admire his incredible generosity, and his ability to touch countless people’s lives in a deeply meaningful way. Simultaneously, I am also aware of the tremendous, and often unnecessary, pain his ambition and temperament caused.

Today, however, I find myself preferring to put his flaws aside and focus on his admirable achievements. You can find his NYTimes obituary here, and rare photos of George from Sports Illustrated here.


Thanks, a really interesting post. We need to remember that, like each of us, public figures are human in all their variety and internal contradictions. And, the same is true for us and others as leaders in our day to day business and other responsibilities.

In recent years, a mystique has emerged of the "good" leader: all sweetness and no faults. But anyone, who has self-knowledge and some knowledge of history understands this is an imaginary concept.

The years hallow and cleanses the memory of great leaders and philanthropists - and it may do the same for us. However, in the meantime, it's worth remembering that all leaders are flawed. That's the human condition. Nonetheless, they are often successful - and often even great.

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