New York Yankees   
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The New York Yankees are known for spending a lot of money in free agency, signifcantly more then just about every team. As a result, agents, players and at times even other teams use this against the Yankees. Owner George Steinbrenner was known for willing to spend a lot of mone, especially for top of the league players. As a result, the Yankees reguarly were the best team in the league an have won more championships then any other sports team in the world. Here are some examples of players who not only got paid a ton, but won a lot for the Yankes.               
The latest examplof the Yankees spending big and getting a very good player is Gerrit Cole. On December 18th, 2019 the Yankees signed him to a 9 year 326 million dollar contract, shattering the last highest paid pitcher's contract. Although he hasn't won a world series with the Yankees yet, he is a 3x all star and only 29 years old.         
One example of the Yankees spending a ton of money for a championship was after the 2008 season. The Yankees finished 3rd in their divison and barely even over .500. This led to the Yankees spending a lot of money to set up for the 2009 season. The Yankees already had a high payroll because in 2001, the Yankees signed Derek Jeter to a 10 year 189 million dollar contract, and in 2008, the Yankees signed Alex Rodriguez to a 10 year 275 million dollar contract. However, that offseason the yankees decided to sign Mark Teixeira to a 8 year 180 million dollar contract, and also signed C.C. Sabathia to a 7 year 161 million dollar contract.           
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