What We Know About the New York Yankees Offseason Strategy

There’s always a lot of wild speculation and rumors every offseason. Here’s a look at the approach the Yankees are most likely to take this winter.

The hot stove season can be a lot of fun because it’s a time of infinite possibilities. A big free agent signing or blockbuster trade can come out of nowhere during the offseason, transforming a mediocre team into an immediate contender. Following the New York Yankees has always been fun in this regard, especially in the good old days, because inevitably they are always in on all the biggest available names.

Things are a little different these days, with New York being uncharacteristically restrained and responsible, but with a few of their bigger contracts beginning to come off the books, we should see at least a little action over the coming months.

Yankees general manager Brian Cashman is more candid than most MLB executives when speaking to reporters, but his front office also has a reputation for secrecy. Generally his biggest moves come out of nowhere, which is notable in this age of constantly flowing rumors.

That said, while we can never be 100% sure what Cashman has up his sleeve, fans who have been paying attention during the early days of the offseason probably have a pretty good idea what is in store for the Yankees this winter.

A Trade for Controllable Young Pitching

The Yankees have made no secret about their desire to acquire young, controllable starting pitchers to shore up the long-term outlook of their rotation. In his recent end-of-season press conference, Brian Cashman stressed that upgrading the pitching staff was his top priority, citing the trade that brought youngsters Luis Cessa and Chad Green to the Bronx as the type of move he would look to make.

Rather than go after an ace like Chris Sale or Sonny Gray, it seems much more likely that Cashman will go under the radar, acquiring arms in the upper-minors that are unproven, but look like they may be ready to help in the big leagues in 2017.

New York already has a pretty impressive number of live arms to compete for jobs next winter, with Luis Severino, Bryan Mitchell, Cessa, and Green all having at least a taste of MLB success this year. None of those guys are even close to a sure thing, however, so if the Yankees don’t want to spend big or give up prospects, the quantity over quality approach seems reasonable.

If New York wants to set its sight slightly higher, a more proven arm with just a year or two of service time would probably interest them, although for a guy like that they’d probably need to deal from their position player depth.

Carlos Rodon of the White Sox, Sean Manaea of the Athletics, and Jon Gray of the Rockies are all examples of young potential frontline starters the Yankees would likely covet if they’re made available.

Quietly Shopping More Veterans

The Yankees reportedly were listening on all of their veteran players at the trade deadline. In addition to the guys that were moved, Brett Gardner, Brian McCann, Chase Headley, Jacoby Ellsbury, CC Sabathia, and Michael Pineda all saw their names surface in the rumor mill.

Of that group probably the two most likely to be moved this winter are McCann and Gardner, but I wouldn’t completely rule out a trade of any of the others.

Given their thin rotation, moving Sabathia or Pineda seems pretty unlikely unless they were part of a larger series of moves. On the other hand, both are entering the final year of their deal and the market for starting pitching should be pretty cutthroat this winter. Big Mike especially would bring back a ton in return this winter because he remains one of the most prolific strikeout artists in the league despite his mixed results.

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Headley would definitely draw interest this winter, but who would the team replace him with? Justin Turner of the Dodgers is the only clearly above-average option on the free agent market and will cost a lot more than Chase. As for Ellsbury, he’s still just good enough that the team has no real incentive to eat the money necessary to move him.

The front-runners to be moved are definitely Gardner and McCann. Even during a down year, Gardy led all Yankees position players in rWAR and is on a reasonable contract.  While they haven’t had a ton of luck finding a fit yet, he remains one of their most marketable vets. It is just a matter of time before Clint Frazier takes his job next year, so the team might as well just get it over with and let Aaron Hicks or Mason Williams hold down to fort to start the season.

It actually probably makes sense to keep McCann even after the emergence of Gary Sanchez as the starting catcher, but the Braves seem likely to make a push for their former star, especially after the injury to top free agent option Wilson Ramos. If they bid high enough, I could see the Yankees being convinced to move him.

Signing Aroldis Chapman

It seems all but certain at this point that Aroldis Chapman will end up back in pinstripes in 2017. Jon Heyman of Today’s Knuckleball recently reported that New York will pursue the top two closers on the market- Chapman and Kenley Jansen.

While Jansen would also be a solid addition, all signs point to the Yankees reuniting with their former closer at some point this season. He’s younger, better, and will not require the team to surrender the 17th overall pick in next year’s draft.

They can also feel pretty confident about Chapman’s health, as well as his ability to pitch in New York and the AL East after his strong first half performance in 2016.

With Mark Teixeira’s $23 million annual salary coming off the books this winter, the Yankees should have no problem offering Chapman a record breaking contract, probably something in the neighborhood of five years $75-90 million.

It is pretty clear from the organization’s recent history that the front office loves having a shutdown bullpen. I can’t remember the last time New York came into a season without at least two top notch late-inning relievers on the roster.

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It also doesn’t hurt that Chapman seemed to enjoy his time playing on the country’s biggest stage and has said multiple times before and after being traded that he would welcome a return. Unless another club is determined to outbid the Bombers, this seems like a lock to happen.