During the Brian Cashman-era, the Yankees front office has evolved their philosophy on trades dramatically. Perhaps it was a product of George Steinbrenner's earlier influence on the team, but seeing top prospects traded away was a regular staple of the Yankees' late 90's success. In fact, Cashman's first trade as GM sent first round picks Brian Buchanan and Eric Milton along with Cristian Guzman and Danny Mota to the Twins for Chuck Knoblauch. Almost exactly a year after, the Yankees made another splash in the trade market by sending Homer Bush, Graeme Lloyd, and David Wells to Toronto for Roger Clemens. Cashman continued to trade for these big name players, which in the mid-2000's included Alex Rodriguez and Randy Johnson.
It was around this time that George Steinbrenner became less involved with the front office. Brian Cashman was given the reigns of the minor league system, and the hope surrounding the Yankees' new ownership seemed to be that the Yankees could develop talent rather than continue to trade for it or sign it. It would allow the organization to lower their budget and create a new core of players following the departure of Bernie Williams and Andy Pettitte and eventually Jorge Posada, Mariano Rivera, and Derek Jeter.
The team was extremely successful in their first few years of handing Cashman control of the farm system. Robinson Cano, Chien-Ming Wang, Melky Cabrera, Brett Gardner, Phil Hughes, Joba Chamberlain, and Ian Kennedy all showed promise in the minors or major leagues, and the youth movement was further endorsed. In 2008, it seems that a lesson was learned regarding prospects, that relying on young players doesn't come without its troubles. There's a certain amount of growing pain that occurs with prospects, and it often takes a season or two for these players to adapt to the major leagues. For an impatient team like the Yankees, who are in perpetual win-now mode, growing pains are hardly tolerated.
Since their failure to make the playoffs in 2008, the Yankees have continued to dominate the free agent market, but they've also been slightly more willing to deal prospects. The front office has modified their strategy to avoid dumping highly touted prospects for over-the-hill players, and they've instead targeted players on other team's cutting block, salary dumps, buy lows, and in rare instances, they've traded prospects for dynamic players, but only ones that offered plenty of team control.
Despite how they performed on the field, the Yankees 2013 season was filled with players obtained from other team's cutting blocks. Cashman and his front office are the most willing to target these kinds of trades lately, simply because it often costs next to nothing. Chris Stewart was probably the most controversial of the players, since he received so much playing time, but the Yankees also found the very important Shawn Kelley in this type of deal.
The next type of trade that the Yankees look for are salary dumps, often in order to add veterans that will push the team to the playoffs. Alfonso Soriano, Vernon Wells, Ichiro Suzuki, Kerry Wood, Lance Berkman, and Ivan Rodriguez were all obtained via the salary dump, and for the most part, the Yankees have been very successful in taking on these aging players without giving up much in return.
If the organization can't find their player via these previous two types of trades, they will consider trading prospects, but only in the sense that they can maximize team control. Most recently, the Yankees dealt Jesus Montero for Michael Pineda, essentially only losing themselves one year of team control between Montero and Pineda. In return, they received the starting pitcher that they needed, and kept the salary of this spot on the roster very low. Another example of this type of trade happened with Detroit, when the Yankees sent Austin Jackson to the Tigers and Ian Kennedy to the Diamondbacks for four years of Curtis Granderson. It seems that if the Yankees are willing to trade top prospects, it will have to be for long-term control.
Finally, those trades for those elite players only months away from free agency have grown extremely rate. Though the Yankees couldn't get the deal done, they desperately tried to trade for Cliff Lee in 2010. These trades are common for teams like the Rangers, but the Yankees don't seem willing to even entertain these deals unless they plan to sign the player in the upcoming offseason. With the rules around player compensation changed in the new CBA, the Yankees are probably even more unwilling to trade for these elite players, since they won't receive compensation picks without a full year of team control.
With this trade history outlined, it seems very unlikely that the Yankees will target some of the big names said to be available this trade deadline. There's no doubt that the team could use a starting pitcher, infielder, and reliever, but it's not the Yankees' style to deal highly touted prospects for players with limited team control. Pitchers like Jeff Samardzija and David Price will require ridiculous prospect packages to obtain, and both players have just a year and a half of team control left. Assuming some teams fall out of contention by June, it also doesn't seem likely that the Yankees would deal prospects for big names like Francisco Liriano, Justin Masterson, or James Shields.
Though the Yankees may be interested in a player like Cliff Lee, I think it's only likely in the case of a salary dump. Lee's most recent injury might be good news for Yankee fans, as it'll inevitably bring down the interest around the league. If his trade value falls far enough, the Yankees may be willing to trade for him if they can avoid giving up a top prospect like Gary Sanchez.
Still, the front office has routinely been more willing to deal for less flashy names, and it seems that the Diamondbacks have two players that fit the Yankees' needs and philosophy perfectly. Brandon McCarthy is a perfect buy low candidate, a salary dump, and a need in the Yankees' rotation. Despite a jump in his 2014 strikeouts and velocity, his ERA sits at 4.67 thanks to a dramatic increase in his home runs and decrease in his left on base rate. The numbers should go down, and with him making the second highest salary in Arizona, he'll likely be very available. The highest paid player on the Diamondbacks is second baseman Aaron Hill, who could provide the Yankees with an upgrade over Brian Roberts and Kelly Johnson, as well as a much needed right-handed bat in the infield. Despite his slow start to the 2014 season, Hill owns a .292/.351/.487 slash with the Diamondbacks over the last three seasons, he has AL East experience and two more years of team control following the 2014 season. With few second baseman available via free agency in the next couple of seasons, the Yankees could answer their infield problems now via a trade with the Diamondbacks.
Ultimately, we'll probably see the Yankees linked to players like Chase Headley and Asdrubal Cabrera, but the Yankees have not been keen on trading good prospects for rentals. If the Rockies fall off, Troy Tulowitzki and maybe even Carlos Gonzalez will hit the trade wire, but the Yankees haven't made that sort of splash since the Alex Rodriguez trade a decade ago. We're probably looking at much smaller names, and with the organization looking to build a new core of players following the departure of Jeter this season, I don't expect the Yankees to trade a top prospect like Gary Sanchez unless they get back a young player with cheap team control.