Examining the Yankees Extension Candidates this Winter

The New York Yankees have a number of core players they could consider offering extensions to during the 2016-2017 offseason.

For a long time the New York Yankees had an explicit rule against negotiating contract extensions with their players before they hit free agency, but they have loosened on that stance in recent years. Robinson Cano in 2008 and Brett Gardner in 2014 are two examples of the team locking up their young players before they hit the market.

The team has more exciting young talent on the roster than at any point in the post dynasty years. With their focus on keeping the budget manageable and building a long-term core, it may make sense for the front office to explore extending one or two of their young stars. Here are a few guys who stand out as possibilities:

Masahiro Tanaka: The Yankees 27-year-old ace is expected to opt-out of his contract following the 2017 season. The three years $67 million on his deal after next year would be the starting point. New York could sweeten the pot by increasing the annual value to $25 million or so and tack on an extra year. Five years and $125 million for Tanaka’s age 29-33 seasons seems fair.

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Didi Gregorius: The team may be better off seeing if Didi’s power is for real next year before committing to him long-term. If they believe he truly got 20 homer pop to go along with his excellent defense, they could lock him up now before he’s really made much through arbitration. Maybe they buy out his three remaining arb years and two free agent years with a five year $40 million offer?

Michael Pineda: Committing big money to the erratic Pineda is a risky proposition, but given the Yankees’ clear need for starting pitching, they may not have much choice. Considering his youth, upside, and the inflated price of free agent pitching, Big Mike isn’t listening on anything less than a five year extension at $15 million-plus annually. Jeff Samardzija got five years $90 million after a much worse year last winter and prices are only going up.

Gary Sanchez: This is definitely a little out there, but if New York really believes in their newest superstar, they could offer him an updated version of Evan Longoria‘s original contract. The Rays bought out the first six years of Longoria’s career for $17.5 and included three team options that increased the total value to nine years $44 million.

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That would have to be adjusted upward for inflation, maybe six years and $30 million and three $25 million team options? Nine years and $105 million for a player with 51 career games as of this writing may seem crazy, but it could end up being a big win for both sides.