They currently have the four highest contracts by total value in the game:
Alex Rodriguez, $275,000,000
Derek Jeter, $189,000,000
Mark Teixeira, $180,000,000
CC Sabathia, $161,000,000
They Yankees awarded the single biggest annual salary in history for one year when they gave Roger Clemens a $28,000,022 deal in 2007. (He only collected around $18 million of that since he did not play until partially into the season.) A-Rod has the second biggest annual salary at $27,500,000.
At $23,000,000 annually CC Sabathia is the highest paid pitcher in the game.
At $15,000,000 annually Mariano Rivera is the highest paid relief pitcher in the game.
At $17,142,857 annually Jason Giambi was the highest paid DH in history.
At $13,100,000 annually Jorge Posada is the highest paid catcher in the game.
At $22,500,000 annually Mark Teixeira is the highest paid first baseman in the game.
At $7,500,000 annually Robinson Cano is the third highest paid second baseman, but he has not hit free agency yet.
At $18,900,000 annually Derek Jeter is the highest paid shortstop in the game.
At $27,500,000 annually A Rod is the highest paid third baseman in the game.
At $13,000,000 annually Johnny Damon and Hideki Matsui are tied for 12th amongst outfielders.
Starting in 2003 the Yankees have spent $1.138 billion in team payroll.
In 2008 Forbes Magazine estimated the value of the Orioles to be $398 million; the Yankees were at $1.3 billion.
In 2008 the Yankees offered only a 1 year deal to Joe Torre for $5 million with a vesting option. They went cheap on their manager and missed the playoffs for the first time since 1994.
I used multiple sources for the salary figures. Feel free to add more…