Brian Cashman - New York Yankees

New York Yankees

Cashman started with the New York Yankees organization as an intern in 1986. In February 1998, he was named Senior Vice-President and General Manager, succeeding Bob Watson.

During Cashman's tenure, the Yankees have won six American League pennants and four World Series championships. Despite the team's success, in 2005 Cashman considered leaving the Yankees due to conflicts with owner George Steinbrenner and organizational disputes between team officials in New York City and Tampa. The Washington Nationals were rumored to be interested in hiring Cashman, which would have brought him back to the city where he attended school. Instead, Cashman agreed to a new contract with the Yankees following the conclusion of the 2005 season which gave him more authority in personnel decisions and paid him an average of $1.3 million more over the following three years.

On September 30, 2008, he signed a new 3-year contract to stay with the Yankees through the 2011 season. Following that season, when the Yankees failed to make the playoffs, Cashman signed CC Sabathia, AJ Burnett, and Mark Teixeira to long-term free agent contracts. These three players played a huge role in the Yankees season, cumulating with a victory in the 2009 World Series.

The Yankees re-signed Cashman to a three-year deal in November 2011.

Following the defeat in the 2010 postseason, Cashman was heavily criticized by fans for a perceived lack of ability.

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