Looking at the Brian Cashman trade record I found myself perplexed. At first you would think that a team with such a rich history of winning and agressive positioning would have traded away a slew of prospects that turned into major leaguers. You would think there would be at least one Jeff Bagwell or John Smoltz type trade that makes you cringe at the Hall of Fame induction ceremony. Maybe at least one "What the hell did you trade Jay Buhner for?". But none can be found. Sure you could make an arguement that guys like Phelps, Prado, Solarte and Burnett could have helped the team win more but even those guys are not going to cause fans to lose sleep. Top prospects such as Jesus Montero and Jose Tabata never lived up to their hype and guys like Cristian Guzman that did go on to have major league careers will probably never be brought up in conversations about the biggest trade mistakes ever made.
The biggest flaw you could find in Cashman's trade approach is that he brings in veterans that are past their prime and then turns around a season or two later and trades them away. I think I began to lose track of how many times the team could trade for and trade away Javier Vasquez. Cashman also has a habit of bringing back the guys he trades away to ensure they have time in Pinstripes. In some of those cases, Tyler Clippard, he should have let them stay away.
Rather you agree with Cashman's track record or disagree, there are five trades that I believe stand out as his defining moments.
5th Best trade - Chapman for Torres, Warren, Mckinney, Crawford
There are some who would say it is too soon to judge this trade but when you look at it all the players that were involved in the trade are currently in the Yankees system so how can there be a downside? Torres will either be a valuable piece of the rebuild or he will be traded to obtain a piece that can help the team win. Warren has already provided bullpen depth this season. When you consider what the Yankees traded to get Chapman and then the fact that they traded Warren for Castro, to have come out of all of it with the assets they now have is impressive. Also as a side note the Cubs broke their World Series drought with the help of these trades so the only fans that could possibly complain would be Reds fans who felt they gave up Chapman for too little.
4th Best trade - Greene for Gregorius
The Yankees needed a shortstop to replace The Captain. When people first saw this trade they questioned giving up pitching for a position player. Some fans wanted so bad to see a Troy Tulowitzki trade happen and felt he was the heir to the position. Cashman and his scouts knew better, Sir Didi was the plan. Didi has gone on to be solid replacement for Jeter and he keeps improving with each season while providing a positive clubhouse presence. Greene meanwhile has a career ERA over 5.00 and does not appear likely to make anyone miss him.
3rd Best trade - Soriano and Arias for Rodriguez
Say what you will about Arod and his ways, but one fact is he was a heck of a ball player and statistical machine. Trading for Rodriguez was by far and away Cashman's biggest trade. Soriano was a star as well so some fans may have questioned the need to trade off but by doing so the Yankees kept Rodriguez from Boston and filled the need in their lineup left by Basketball Boone. Rodriguez went on to provide WAR of 7.6, 9.4, 4.5 and 9.4 in the first four seasons while Soriano posted 2.0, 1.6, 6.1 and 4.3. Rodriguez also provided a much needed post season boost towards the 2009 World Series trophy run.
2nd Best trade - Smith, Henry, Sanchez and Monasterios for Abreu and Lidle
Just reading the names of the players traded should be enough to justify this as being a great trade. Although Abreu was starting to see his numbers decline, he proved to be a great bat in the lineup and was able to put up numbers that helped the team win. He finished in the top 20 in MVP voting twice during his Yankees career and drove in 100 runs 3 times. What makes this trade so great is that none of the guys the Yankees sent matched the production that the team received from Abreu. CJ Henry was the headliner of the group and he never even saw major league time. He also returned to the Yankees organization a few years later.
Number 1 The Best - Betemit, Marquez, Nunez for Swisher, Texeira
Let the debate commence but the best trade that Cashman has made was for Nick Swisher. Swisher was coming off a down year in which he only hit .219 with his lowest OPS. The Yankees needed a replacement at first and had yet to sign Texeira who appeared destined for Boston. However instead of manning first, Swisher solidified the outfield allowing Matsui to DH full time. Swisher was a positive clubhouse presence and was a key part to the 2009 World Series run. Again the players traded for Swisher never provided the same value that he brought to the team. What makes this trade stand out above the rest is that it is still providing value today. Due to Swisher's production with the Yankees he gained them a compensation draft pick that was used to draft Aaron Judge.
There are many more trades that Cashman has come out to the better on. The list of Hall of Famers and All Stars that he has traded for is numerous and you will be hard pressed to find where he sent back the same level of talent. Cashman also has the distinction of trading away two Dallas Cowboys starting quarterbacks. You can argue all you want about Cashman as a GM but his expertise in making trades is not deniable. Overall my assessment of Cashman is that he is a ninja extraordinaire.