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 Clean Out of the 40-man Roster

Since the regular season ended, the Yankees have dropped five players from their 40-man roster: outfielder Eric Young Jr., infielder Donovan Solano, and relievers Blake Parker, Kirby Yates, and Anthony Swarzak. They also outrighted reliver J.R. Graham with a few days left in the season. With Mark Teixeira retiring and Billy Butler expected to leave via free agency, that leaves New York eight open spots total.

When first baseman Greg Bird was activated off the 60-day DL to play in the Arizona Fall League, that filled up one of those open spots. There are six other guys currently on the disabled list that will need to be added to the roster following the end of the World Series, but at least three of them, Nathan Eovaldi, Dustin Ackley, and Conor Mullee, are strong candidates to be non-tendered.

Assuming they are, that leaves the Yankees with four openings on the 40-man to protect Rule 5 eligible players. Cashman already revealed that catcher Kyle Higashioka will be added to the roster imminently, and top prospects like Jorge Mateo, Miguel Andujar, Domingo Acevedo are also locks.

As things currently stand, the Yankees won’t have room for promising pitchers like Dietrich Enns, Giovanny Gallegos, or Tyler Webb unless they make more cuts in the coming weeks. 29-year-old rookie lefty Richard Bleier seems like an easy guy to let go, as does Johnny Barbato, who didn’t even receive a September call up after starting the year in the MLB bullpen.

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.