Why wasn’t George Steinbrenner ready to sign Derek Jeter?

Derek Jeter, his former teammates, and ex-coach Joe Torre at Yankee Stadium on hi HoF day; inset is George Steinbrenner
Sara Molnick
Thursday March 16, 2023

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There was a time when Yankees owner George Steinbrenner was not too keen to sign their longest captain Derek Jeter. However, destiny was ready to see Jeter becoming a New York Yankees legend, and “the Boss” even couldn’t stand on his way to the Bronx. And what happened after that is history.

When he first played in the major leagues, Derek Jeter was very young. At the time, not many people were willing to take high school students and George Steinbrenner was one of them. However, a Yankees scout encouraged the owner to take a chance on the talent, who became their No. 6 choice in the 1992 draft.

This was revealed by Bill Livesey, who is an adviser to the Pittsburgh Pirates. He was the man credited with the signing of the Yankees’ “Core Four” while working as their director of scouting between 1991 and 1996. While speaking to CSmonitor in 2014, he told:

“Mr. Steinbrenner was not really high on taking high school kids, simply because they were too long from the big leagues. So, we had to convince him. He asked me how long it was going to take for him to be in the big leagues. It was a little bit of the fib: I told him four years.”

The five teams that picked before the Yankees got the chance ignored Derek Jeter. This saved the Yankees shortstop legend from going to Cincinnati, Baltimore, Cleveland, Houston, or Montreal.

Derek Jeter fielding

Derek Jeter went on to become a legend

Derek Jeter was picked by the Yankees in the 1992 draft and got a $700,000 bonus when he signed with the Yankees. He made his debut in the major leagues in 1995 when he was 20 years old and quickly reached new heights.

Derek Jeter’s first game in the major leagues was on May 29, 1995, but he only played in 13 games that year. But he started for the Yankees on the first day of the 1996 season and went on to have a Hall of Fame career.

In 1996, he helped the Yankees beat the Atlanta Braves in the World Series and was named the team’s starting shortstop. Derek Jeter also won the Rookie of the Year Award.

From left: Derek Jeter after a splendid game in 1996, with his father , waving four after winning his fourth World Series ring, women fans trying to approch him at Boston, a woman fan during his batting practice.

From 1998 to 2000, when the team won championships, Derek Jeter kept getting better. In 1998, he came in third place for the Most Valuable Player award in the American League. In 1999, he set many career highs, and in 2000, he won the MVP awards for both the All-Star Game and the World Series.

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