$27m would be 3rd highest. Per Cot's Average annual value The highest-paid players in baseball history, by average annual value: 1. Roger Clemens, $28,000,022 (2007) 2. Alex Rodriguez, $27,500,000 (2008-17) 3. Alex Rodriguez, $25,200,000 (2001-10) 4. Ryan Howard, $25,000,000 (2012-16) . . Josh Hamilton, $25,000,000 (2013-17) . . Felix Hernandez, $25,000,000 (2013-19) 7. Zack Greinke, $24,500,000 (2013-18) 8. CC Sabathia, $24,400,000 (2012-16) 9. Cole Hamels, $24,000,000 (2013-18) . . . Cliff Lee, $24,000,000 (2011-15) . . . Albert Pujols, $24,000,000 (2012-21) 12. Prince Fielder, $23,777,778 (2012-20)