Brian Cashman has been the New York Yankees' general manager since 1998. That is a long time to be in one place in any line of work, let alone one that is so public and demanding as the GM of one of the most famous professional sports teams in the world (especially when his boss was, well, The Boss).
Since no one is perfect, it is natural to expect mistakes to be made along the way. No matter how hard decision makers try, it's inevitable. Cashman is no exception. Like every GM, there have been trades and free agent deals that have been successful and those that have failed. Every deal also carries a certain amount of risk, and none are more riskier than the blockbusters that come about every so often.
We've seen over the years how young players, whether as prospects in the minors or very early in their big league careers, can make the team who trades them feel some measure of regret. Just for some recent examples:
When looking at Cashman's history of blockbuster trades, however, there doesn't seem to be an instance where he has given up someone the organization wishes it didn't a few years after the deal. Consider the following blockbusters:
-Chuck Knoblauch (acquired from the Minnesota Twins for Brian Buchanan, Cristian Guzman, Eric Milton, and Danny Mota).
-David Justice (acquired from the Cleveland Indians in 2000 for Ricky Ledee, Jake Westbrook, and Zach Day)
-Randy Johnson (acquired from the Arizona Diamondbacks in 2005 for catcher Dioner Navarro, pitcher Brad Halsey, and pitcher Javier Vazquez)
-Bobby Abreu (acquired from the Philadelphia Phillies in 2006 for shortstop C.J. Henry, pitcher Matt Smith, Jesus Sanchez, and pitcher Carlos Monasterios)
-Curtis Granderson (acquired from the Detroit Tigers in a three-team swap with the Yankees dealing outfielder Austin Jackson and pitcher Phil Coke to the Tigers and pitcher Ian Kennedy to the Diamondbacks).
-Michael Pineda (acquired from the Seattle Mariners in 2012 with Vicente (formerly Jose) Campos for Jesus Montero and Hector Noesi)
Looking at just these six trades, the prospects/young players Cashman dealt away who experienced sustained success at the big league level were Buchanan, Navarro, Jackson, and Kennedy. Jackson has the highest career WAR so far out of the four (22.2). However, when the Yankees dealt each, they dealt from positions of depth. There was no need for Guzman or Navarro with Derek Jeter at short and Jorge Posada entrenched behind the plate. The Yankees also felt they had rotation depth behind Kennedy heading into 2010, as well as upside in the minors in terms of outfielders (plus there was no spot on in the big league outfield with Brett Gardner, Nick Swisher, and Granderson).
Ledee and Buchanan became no more than bench players. Milton, who was the Yankees first round pick in 1996, pitched for eleven seasons, but finished with a career 4.99 ERA in 271 games. Of those in the Abreu trade, Monasterios and Smith combined to pitch 67 career games between them and Henry, the prize of the deal who the Yankees selected 17th overall in the 2005 draft, never reached the big leagues before giving up the sport entirely. Montero has been a disaster in Seattle, and Noesi is now pitching in the Korea Baseball Organization.
The 2004 trade that netted the Yankees Alex Rodriguez from the Texas Rangers is not included here for a couple of reasons: first, the amount of money left on Rodriguez's deal at the time (he was only three years into his initial ten-year, $252 million contract) gave the Yankees the ability to negotiate the price tag down a bit in the sense that they didn't end up giving away all the top prospects in their system. The Rangers were desperate to get out from the entirety of that contract, and the Yankees knew that by taking on even a portion of the contract they would be able to hold onto some of their better prospects.
When the Yankees traded for A-Rod, Alfonso Soriano was already an established big league talent, having played three full seasons by that point. As for the second piece of the trade that went to Texas, the Yankees gave the Rangers their choice between shortstop Joaquin Arias and a little-known second baseman named Robinson Cano. The Yankees would have given up Cano had Texas chosen him, so it was not necessarily a stroke of genius on the Yankees' part that allowed Cano to stay in the organization. The Rangers just made the wrong choice (which is easy to say now when looking back over a decade later).
Why does it appear the Yankees are so good at holding onto the right prospects? Part of it is luck, undoubtedly. No matter what, no one knows for sure if and when a young player will ever break out. However, it can't be all luck because it could be argued that this trend predates Cashman. Former GM Gene Michael grew a reputation for knowing exactly which prospects to trade and which ones to keep.
In Yankees beat writer Joel Sherman's book about the 1996 Yankees Birth of a Dynasty, he included this little blurb about Michael:
"In that quest [to acquire elite talent in 1995], he traded six homegrown talents (Keith Heberling, Lyle Mouton, Fernando Seguignol, Marty Janzen, Jason Jarvis, and Mike Gordon) to obtain Jack McDowell, John Wetteland, and David Cone...Michael has a sixth sense of which prospects to protect, such as Derek Jeter, Andy Pettitte, Mariano Rivera, Bernie Williams, and Jorge Posada, and which ones to move. After an era in which the Yankees notoriously traded eventual stars Jay Buhner, Doug Drabek, Willie McGee, and Fred McGriff for veteran waste, Michael was never burned by any of the youngsters he dealt. Some turned into good players, such as J.T. Snow, but most did not, and none became star performers elsewhere."
This, too, seems to be Cashman's genius. Think about it–years after these trades went down, is there one name listed above that you wish the Yankees didn't trade? It's often said the Yankees succeed solely based on their financial might. Yes, money is a great thing to have and it certainly helps. However, Cashman and his scouts deserve much more credit than that. Just from these few examples, there does appear to be something that allows the Yankees to come out ahead in these blockbuster-type trades. Is it "a sixth sense of which prospects to protect"? Is it the fact that the Yankees can go out and sign big free agents, thus reducing their reliance on huge trades to bring in talent, which reduces the chance a big trade goes wrong for them? Maybe it's Cashman's ability to know exactly when to take advantage of a team that is desperate to trade away an expensive or unhappy star?
Whatever the case, Cashman's Yankees have done an above average job at protecting the right prospects and not giving up players that came back to haunt them. It's easy to say "of course Cashman will succeed in New York, look at the payroll he is given!" Clearly, his job is so much more difficult than that. Did the Yankees win championships with Abreu and Granderson and Johnson? No. But did those acquisitions put the Yankees in positions to battle for one? Absolutely. When tested, Cashman has proven to be a smart and cautious dealer, and the Yankees are clearly the better for it.