The main area that needs improving for the New York Yankees is their rotation pitching. With a weak free agency market in 2016-2017, trading for an ace seems like the most reasonable solution. Chris Sale of the Chicago White Sox and Jose Fernandez are on top of the Yankees lists.
Whether they make the playoffs or not (2.5 games behind the wild card spot), the Yankees have very little they carry over into next season in terms of starting pitching quality. C.C. Sabathia, Masahiro Tanaka and Michael Pineda. That’s not a whole lot, and except for Tanaka, not all that great. There’s the foursome of Luis Severino, Chad Green, Luis Cessa and Bryant Mitchell, but none of them have been good enough consistently to prove they deserve to be part of the Yankees 5-man rotation in the future.
So who are the players the Yankees might go after? They’ve been linked quite often with Fernandez of the Miami Marlins, but so have a lot of other teams. Fernandez is going to become very expensive very soon, something the Marlins don’t particularly like. The Yankees have the prospects to convince the Marlins to move him at some point in the next two seasons. Overall, a lot of the moves the Yankees have made in the last year have been to create a deep enough farm system that it provides them with assets to include in trades, as they move away from big free agency spending that they were so famous for over the years.
The Chicago White Sox hold two players the Yankees (and a lot of other teams) are extremely interested in: Chris Sale and Jose Quintana. Both young, both with very affordable contracts, and both playing for a team that hasn’t been to the postseason in a long time. Sale is also known for his run-ins with the White Sox front office, and their misguided way of trying to win while playing in the shadow of a successful-again Cubs might make Sale push hard for a trade. It certainly makes sense for the dead-end White Sox to consider this more seriously than ever before.
There are other pitchers the Yankees might try to deal for in the offseason: Ervin Santana, who a lot of teams looked into before the deadline this season, or Chris Archer. In any case, the Yankees seem to be a tier behind teams we would consider serious contenders, and right now only the fourth best team in the AL East. In order to make that jump, adding a quality arm to their rotation is probably the most important thing on their to-do list.