| 1. | Alex Rodriguez - New York Yankees - Baseball - 10 years (2008-2018) $275,000,000 |
| 2. | Alex Rodriguez - Texas Rangers - Baseball 10 years (2001-2010) $252,000,000 |
| 3. | Derek Jeter - New York Yankees - Baseball - 10 years (2001-2010) $189,000,000 |
| 4. | Joe Mauer - Minnesota Twins - Baseball - 8 years (2011-2018) $184,000,000 |
| 5. | Mark Teixiera - New York Yankees - Baseball - 8 years (2009-2016) $180,000,000 |
| 6. | CC Sabathia - New York Yankees - Baseball - 7 years (2009-2015) $161,000,000 |
| 7. | Manny Ramírez - Boston Red Sox - Baseball - 8 years (2001-2008) $160,000,000 |
| 8. | Fernando Alonso - McLaren - Auto racing - 4 years (2007-2010) $160,000,000 |
| 9. | Kimi Räikkönen - Ferrari - Auto racing - 3 years (2007-2009) $153,000,000 |
| 10. | Miguel Cabrera - Detroit Tigers - Baseball - 8 years (2008-2015) $152,300,000 |
| 11. | Todd Helton - Colorado Rockies - Baseball - 11 years (2001-2011) $151,500,000 |
| 12. | Johan Santana - New York Mets - Baseball - 6 years (2008-2013) $137,500,000 |
| 13. | Kobe Bryant - Los Angeles Lakers - Basketball - 7 years (2004-2011) $136,400,000 |
| 14. | Alfonso Soriano - Chicago Cubs Baseball - 8 years (2007-2014) $136,000,000 |
| 15. | Michael Vick - Atlanta Falcons - American football - 10 years (2005-2014) $130,000,000 |
| 16. | Jermaine O'Neal - Indiana Pacers - Basketball - 7 years (2003-2010) $126,558,000 |
| 17. | Kevin Garnett - Minnesota Timberwolves - Basketball - 6 years (1999-2005) $126,000,000 |
| 18. | Barry Zito - San Francisco Giants - Baseball - 7 years (2007-2013) $126,000,000 |
| 19. | Vernon Wells - Toronto Blue Jays - Baseball 7 years (2008-2014) $126,000,000 |
| 20. | Rashard Lewis - Orlando Magic - Basketball - 6 years (2007-2013) $126,000,000 |
| 21. | Michael Schumacher - Ferrari Auto racing - 4 years (1996-1999) - $124,000,000 |
| 22. | Alexander Ovechkin - Washington Capitals - Ice hockey - 13 years (2008-2021) $124,000,000 |
| 23. | Chris Webber - Sacramento Kings - Basketball - 7 years (2001-2007) $122,718,750 |
| 24. | Tim Duncan - San Antonio Spurs - Basketball - 7 years (2003-2010) $122,007,704 |
| 25. | Mike Hampton - Colorado Rockies - Baseball - 8 years (2001-2008) $121,000,000 |
| 26. | Shaquille O'Neal - Los Angeles Lakers - Basketball - 7 years (1996-2003) $120,000,000 |
| 27. | Jason Giambi - New York Yankees - Baseball - 7 years (2002-2008) $120,000,000 |
| 28. | Matt Holliday - St. Louis Cardinals - Baseball - 7 years (2010-2016) $120,000,000 |
| 29. | Carson Palmer - Cincinnati Bengals - American football - 9 years (2006-2014) $119,750,000 |
| 30. | Carlos Beltrán - New York Mets - Baseball - 7 years (2005-2011) $119,000,000 |
| 31. | Ken Griffey, Jr. - Cincinnati Reds - Baseball - 9 years (2000-2008) $116,500,000 |
| 32. | Donovan McNabb - Philadelphia Eagles - American football - 12 years (2002-2013) $115,000,000 |
| 33. | Gilbert Arenas - Washington Wizards - Basketball - 6 Years (2008-2013) $111,000,000 |
| 34. | Juwan Howard - Washington Wizards - Basketball - 7 years (1996-2003) $105,000,000 |
| 35. | Kevin Brown - Los Angeles Dodgers - Baseball - 7 years (1999-2005) $105,000,000 |
| 36. | Jason Kidd - New Jersey Nets - Basketball - 6 years (2003-2009) $103,572,000 |
| 37. | Ben Roethlisberger - Pittsburgh Steelers - American Football - 8 years (2008-2015) $102,000,000 |
| 38. | Albert Pujols - St. Louis Cardinals - Baseball - 7 years (2004-2010) $100,000,000 |
| 39. | Carlos Lee - Houston Astros Baseball - 6 years (2007-2012) $100,000,000 |
| 40. | Shaquille O'Neal - Miami Heat - Basketball - 5 years (2005-2010) $100,000,000 |
| 41. | Brett Favre - Green Bay Packers - American Football - 10 years (2001-2010) $100,000,000 |
| 42. | Albert Haynesworth - Washington Redskins - American Football - 7 years (2009-2016) $100,000,000 |