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Ask Pinstripe Alley 12/7/16: Should the Yankees sign a free agent starting pitcher?

Should the Yankees sign Chapman and Jansen with the intention of flipping them at the deadline?

MLB: Boston Red Sox at New York Yankees Brad Penner-USA TODAY Sports

Last week I asked for questions for our Yankees mailbag, and plenty of questions were submitted. I decided to split my answers into two posts to try and cover as many submissions as I could. Here is part two of my answers.

Mark asked: Who was the last player to bat over .300 on the Yankees. Who do you think will be the next? And why has there been a drought?

The last player to bat over .300 with the Yankees was Robinson Cano in 2013, and he also hit above .300 every year from 2009-2012. Clearly the Yankees have been suffering from a severe lack of Cano. Carlos Beltran may have been on his way to ending the drought had he stayed with the Yankees in 2016 since he slashed .304/.344/.546 during his partial season with the team. Since Beltran doesn’t count, Didi Gregorius was the closest to .300, ending the season batting .276 this year.

I have no idea who the next to do so will be, but Gary Sanchez did hit .299/.376/.657 during his two months with the Yankees. Of course, he probably can’t keep that up, but he could come close. I guess one of the reasons that no one in the lineup has hit over .300 since 2013 has to do with who the Yankees signed during that offseason. No one expected Brian McCann to hit like that, and Jacoby Ellsbury and Carlos Beltran were both several years removed from seasons where they hit over .300.

AJSMind asked: Considering the lackluster SP'ers available and the Yanks guarded expectations for 2017 would it be better to allow the young pitchers in the the Yankees organization to gain experience in the MLB rotation rather than signing a free agent to a multi-year deal? Bryan Mitchell, Luis Cessa and Chad Green showed signs of being useful pieces at the back-end of the rotation in the same two spots that are open now and this was done in the the 2nd half when the Yanks went 34-30 after the trade deadline.

I will say that I am happy that Rich Hill found his multi-year deal with the Dodgers and not with the Yankees. I think it is in the Yankees’ best interest to avoid handing out a multi-year deal to any of the free agent starters out there, though I wouldn’t be upset if someone ends up with a cheap one-year deal.

As things currently stand, the rotation is not great. There’s Masahiro Tanaka, CC Sabathia, Michael Pineda, and two empty spots. Luis Severino could take the fourth spot, but he struggled last year and had to be removed from the rotation. It would be fine to give one of those spots to Severino, Mitchell, Cessa or Green. I’d prefer to see Brian Cashman pull off some sort of trade for a starting pitcher to fill in the fifth spot, though.

David asked: With the great assets the Yankees were able to acquire at the deadline last season by dealing Miller and Chapman, does that mean that signing every closer on the market and potentially trading them at the deadline again this coming year is a fair strategy for Cashman to consider this offseason?

Well, the Yankees have apparently made offers to both Aroldis Chapman and Kenley Jansen, so maybe this is Cashman’s master plan (although Sweeny Murti indicated that there is a “less than zero” chance that the Yankees would sign both closers). Realistically, this would be a pretty large gamble since the Yankees wouldn’t be able to guarantee that either player would be healthy at the deadline, or that there would necessarily be any teams willing to take on something like the five-year contract that Chapman supposedly wants. It would be amusing to watch Cashman drain all of the other farm systems though.

Zach asked: Who are the names to watch in AAA that are most likely to fill in if there are open spots in the rotation?

Lefty Dietrich Enns is coming off of a great season. He split his time between Trenton and Scranton with a 1.73 ERA through 135 innings. 2016 was also a good year for Jordan Montgomery, who finished the season with 8.67 K/9 and a 2.13 ERA. Another pitcher who could help the rotation at some point is Ronald Herrera, who came to the Yankees in the deal that sent Jose Pirela to the Padres last offseason. Brady Lail and Chance Adams could also be in the mix.