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Derek Jeter: Leaders Learn From Failure

From left, BCW Chairman Anthony Justic; BCW Executive Vice President and COO John Ravitz; Derek Jeter; BCW President and CEO Marsha Gordon; BCW Vice President Membership & Programs Sara James and BCW Director of Special Events Amanda DePalma

In a candid, at times humorous, at times moving presentation to the Business Council of Westchester Tuesday night, Yankees legend Derek Jeter told the audience of more than 300 people who attended the event at the Marriott in Tarrytown that the path to becoming a leader is not always about winning. The program, in partnership with Steiner Sports Management, focused on Jeter’s success as a leader on the playing field, and currently as an entrepreneur and founder of business ventures such as The Player’s Tribune, an online sports media platform.

From his early years to the pinnacle 1998 season, through his retirement, Jeter, one of the most respected players in baseball, gave some tips on how his experiences shaped his skills as a leader. Here are some highlights:


Jeter credited his parents with giving him a strong foundation. He said their honesty and acceptance of both his attributes and failings gave him the courage to believe in himself.

“My family is extremely close,’’ he said. “My parents have always been open and honest with me. My parents were there for me. They were the most positive people I ever met.’’


Jeter said he learned about leadership from Yankees Manager Joe Torre who gave him the best gift of all: allowing him to fail. Jeter said that as a young player, Torre always remained calm even when Jeter made mistakes, encouraging him to swing for the fences instead of being cautious.

“Mr. Torre gave me the opportunity to fail, therefore he gave me the opportunity to succeed,’’ said Jeter.”


“I am very good at knowing what I don’t know,’’ he said. “In order to learn, I try to surround myself with people who are much smarter, which isn’t hard.”


Jeter said as a leader he learned that if you want people to follow you, you have to recognize their individual strengths and weaknesses. “You treat everyone fairly, but you don’t treat everyone the same. Take time to get to know people. Some guys you can yell and scream at and others need hugs.’’


Jeter said he first started thinking about retirement in 2013 when he broke his ankle. The idea about starting an online platform where players could express themselves without the “filter” of the media appealed to him, perhaps because he often felt misunderstood by the journalists who covered him, he said.

“Find things to be passionate about,’’ he said. “I wanted to equip athletes with the tools to get their message out in a professional way.’’


Jeter said he wanted to be a shortstop for the Yankees since 10th grade and he never gave up on that dream.

“My dream was always to be a shortstop for the New York Yankees. That was it and everything that’s come along with it has been icing on the cake.”

His next big dream: “I want to own a team. You applaud, but does anybody out there have any money?”


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