Next season will be Brian Cashman’s 20th as general manager of the New York Yankees. Since taking the reins in February of 1998, he has steered the club to fifteen playoff appearances, twelve first place finishes in the AL East, and four World Series championships. He is the third longest tenured general manager in Major League Baseball, behind only Billy Beane and Brian Sabean.
For a guy with so much success on his resume, he is far from universally beloved among the fan base. While he can’t take credit for assembling all of the talent during the dynasty years, he also endured one of the most meddling owners in history for most of his first decade at the helm, making his performance difficult to evaluate in the early years of his administration. Cashman has had much clearer authority over baseball decisions since 2006, which the team agreed to give him rather than lose him to the Nationals, who were reportedly pursuing him following the tumultuous 2005 season.
To celebrate his upcoming 20th anniversary as the man in charge of the team’s daily operations, here’s a list of the 20 transactions during his regime that have had the greatest impact on the club’s success, measured by WARP. These are not necessarily his smartest or best moves, but the ones that have had the most effect on the team in terms of pure wins. The cost of each win is not taken into consideration because, come on, why should it? Until recently, finances were the last thing that went into New York’s decision making. For a trade, WARP accumulated under the original contracts of any assets given up is subtracted from the total. Future value that may be accumulated after the 2015 season is not taken into account. Hall of Fame voters should take note as to who was perhaps the second most important signing in recent Yankees’ history.
| Transaction | Total WARP | Annual WARP | Years |
|---|---|---|---|
| 1. Derek Jeter’s 10-year, $189 million extension | 28.6 | 3.2 | 2002-2010 |
| 2. Mike Mussina’s six-year, $88.5 million contract | 27.7 | 4.6 | 2001-2006 |
| 3. Alex Rodriguez’s 10-year, $275 million extension | 23.4 | 2.9 | 2008-2017 |
| 4. Bernie Williams’s seven-year, $87.5 million contract | 22.5 | 3.2 | 1999-2005 |
| 5. Jason Giambi’s seven-year, $120 million contract | 21.2 | 3 | 2002-2008 |
| 6. Buying out Robinson Cano’s three free agent years for $39 million | 19.2 | 6.4 | 2011-2013 |
| 7. Signing Robinson Cano as an international free agent | 19.2 | 3.2 | 2005-2010 |
| 8. Buying out five of Jorge Posada’s free agent years for $40 million | 17.8 | 3.6 | 2003-2007 |
| 9. Signing Orlando Hernandez as an international free agent | 17.6 | 3.5 | 1998-2002 |
| 10. Mark Teixeira’s eight-year, $180 million contract | 15.8 | 2.3 | 2009-2016 |
| 11. Drafting Brett Gardner in the third round of the 2005 draft | 15.1 | 2.2 | 2008-2014 |
| 12. CC Sabathia’s original three-year, $60 million contract before opting out | 14.8 | 4.9 | 2009-2011 |
| 13. Acquiring Alex Rodriguez from the Rangers for Alfonso Soriano and Joaquin Arias | 14.7 | 3.7 | 2004-2007 |
| 14. Acquiring Nick Swisher from the White Sox for Wilson Betemit, Jeffrey Marquez, and Jhonny Nunez. | 14.1 | 3.5 | 2009-2012 |
| 15. Signed Chien-Ming Wang as an international free agent | 12 | 2.4 | 2005-2009 |
| 16. Hideki Matsui’s three-year, $21 million contract | 11.1 | 3.7 | 2003-2005 |
| 17. Johnny Damon’s four-year, $52 million contract | 10.7 | 2.7 | 2006-2009 |
| 18. Signing Alfonso Soriano as an international free agent | 9.9 | 2.5 | 2000-2003 |
| 19. Gary Sheffield’s three-year, $39 million contract | 9.7 | 3.2 | 2004-2006 |
| 20. Hideki Matsui’s four-year, $52 million extension | 8.6 | 2.2 | 2006-2009 |
Honorable mentions
- Drafting David Robertson in the 17th round of the 2006 draft (8.1 WARP, 2008-2014)
- Mariano Rivera’s three-year, $45 million contract (7.7 WARP, 2008-2010)
- Drafting Phil Hughes in the first round of the 2004 draft (7.6 WARP, 2007-2013)
- Roger Clemens’s two-year, $30.9 million extension (7.4 WARP 2001-2002)
- Buying out three of Andy Pettitte’s free agent years for $26 million (7.3 WARP, 2001-2003)
One thing that jumps out about these moves is that the majority are free agent signings or draft picks. Many of the most notable iconic trades Cashman has completed have ended up negatively for the Yankees judged purely by net WARP. The Chuck Knoblauch, Roger Clemens, Curtis Granderson and David Justice trades were all net losses for the organization by that measure. Most of these fit into the mold of shipping out prospects to land an established veteran. The Clemens deal is the exception. He was just completely out-performed by David Wells over the two years of control each had remaining at the time of the trade.
The good news is that Cashman seems to have learned from his mistakes and has held off on trading his top prospects in recent years, focusing on building through the farm. The bad news is that the Yankees seem to have sworn off free agents completely, at least for the time being, which is the wrong lesson to have learned from the last two decades. A lot of these big free agent deals are the reason the Yankees have been so successful in my lifetime. Yes, limiting the length of contracts given to aging players and holding onto draft picks are excellent strategies, but it is difficult to build a winner without supplementing your homegrown core through free agency.
Cash is currently in the second year of his latest three year extension. His future with the team may depend on how the Yankees’ young core in the upper-minors develops, as well as how some of his reclamation projects pay off. For the moment, he is as secure as any executive in baseball. He seems to have the full support of ownership in recent years. When he moves on from the Yankees’ GM position, it will probably be on his terms.
Lead photo: Brad Penner / USA Today Sports