The Yankees made the postseason last season, ending a two-year playoff drought, which in the Bronx felt like a decade-long drought. Nevertheless, the Yankees limped into the playoffs and failed to get past the one game playoff – getting shutout by Dallas Keuchel and the Houston Astros. Some may call the 2015 season a success for the Yankees because they overachieved. But those people probably do not live in New York. Any season that does not end in a championship is a failure for the twenty-seven time champs.
The Yankees have made it clear that they will not be big spenders in free agency until they shed some salary – Carlos Beltran, Mark Teixeira, and CC Sabathia are all free agents after the 2016 season. Moreover, the Yankees have shown a desire to get younger while still staying competitive. Cashman did an excellent job of this last offseason acquiring both Didi Gregorious and Nathan Eovaldi – in separate deals – for Shane Green, Martin Prado, and David Phelps. Both Gregorious and Eovaldi proved to be key contributors to the 2015 Yankees. This offseason has been no different for Cashman and the Yankees. Cashman has continued to look to get younger – and better – via the trade market. He has managed to do this again by acquiring Aaron Hicks, Starlin Castro, and Aroldis Chapman – in three separate trades – for John Ryan Murphy, Adam Warren, Brendan Ryan, and four prospects (none of which were their top prospects). Cashman managed to get three major league ready players for that return. Pretty impressive.
So, lets take a look at the major questions that the New York Yankees face as we turn the calender to 2016.