The Hall of Famer Derek Jeter had only one dream as a kid. It was to play baseball and only for the New York Yankees. After working harder than most people, he finally made his dream come true. 

Jeter spent his 20-year Major League Career only with the New York Yankees. The team’s management had miscommunications which led to some conflicts between the shortstop and the General Manager. 

Having made his debut in 1995 in the Major League, Jeter became “Rookie of the Year” the following year. And also helped his team win a world series against the Atlanta Braves. 

What was the conflict between GM and Derek Jeter?

Before the 1999 offseason, Jeter got eligible for salary arbitration for the first time. In the arbitration, the shortstop asked for $5 million dollars. Which, Cashman rejected and counter-offered him an arbitration of $3.2 million. 

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The counter-offer was once again rejected by the shortstop’s agent, Casey Close. Later on, there was silence from both sides for over two weeks, which surprised Jeter and Close as well. 

On this, Cashman said, “All I know is I made the last offer, so the one that should be surprised and baffled that they have heard nothing is me. [Close] rejected the offer and told me it was because Derek did not know what the right number to settle it was. So I’m waiting to hear what their counteroffer is. The ball is in their court.”

But Close was not the one who was going to break the silence.

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Also, he was pretty disturbed by the Yankees’ inability to draft up a deserving contract for one of the best players in the American League.

Did the Yankees offer anything to Jeter?

Before the arbitration in 1999, the New York Yankees offered the shortstop a five-year contract for a $25 million enticement the very last season. 

On this, Close said, “Five years is a great offer for a sports writer or a sports agent, but five years at $25 million is not value for one of the best players in the American League.”

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Close was pretty adamant about getting Jeter the contract he deserved. He also kept wondering if the Yankees want Derek Jeter to be a long-term player, then why they still haven’t made a long-term offer for the same.