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Possible Yankees extension candidates

The Yankees are changing their approach to building the franchise. With MLB.com tossing seven Baby Bombers on their Top 100 Prospects list, the team has moved to building through the farm system rather than signing free agent after free agent. This new mindset can be attributed in part to the slew of aging contracts they’ve been stuck with over the last few years, as well as the diminishing quality of talent found in the free agent market.

Teams are following a trend of trying to extend players before they hit free agency. The downside of paying players more now, is hopefully offset by the savings teams see as players enter their prime years. So with the shifting environment of baseball, who are some possible Yankees extension candidates?

Recent Extensions

The Yankees have had a general policy of not looking at new contracts until current ones expire, whether it’s players, managers, or the front office. There have really been only two contract extensions signed in the last decade (three if you count CC Sabathia‘s extension, which I won’t since it was somewhat connected to his opt-out clause approaching).

In 2008, Robinson Cano received a four-year extension worth $28 million, which included options over an additional two years worth $27 million. Brett Gardner signed a four-year, $52 million extension in 2014. Both players had some similarities in that they were homegrown, well-liked both in the organization and by fans, and playing at a fairly high level.

Extension Candidates

So who are some current Yankees extension candidates? Right now, there are fewer options than may be typical for a team. The Yankees consist mainly of either aging veterans already being paid a hefty chunk of change or young rookies with little to no major league experience.

Didi Gregorius:

Even with Gleyber Torres drawing headline after headline, Gregorius makes the most sense to try and extend; worry about keeping players and moving them around the diamond if need be rather than losing them. Last year Didi took a really big step forward. I mean really big. After not hitting more than 10 HR in any of his major league seasons, the guy put up 20 in 2016 to go along with a .276/.304/.447 slash line. Those are great numbers for a strong defensive shortstop and he’s not yet 27. Remember Didi had a lot of hype when he was a prospect and was considered somewhat of a bust until the Yankees acquired him. Definitely worth it in my book.

Dellin Betances:

Here’s an example of a homegrown player that fans love. Betances doesn’t become a free agent until 2020, so it may be too early to look at something like this; he could be a potential extension option in a few years. The problem for the Yankees right now is a) they signed Aroldis Chapman at big money for five years and b) relievers are currently getting paid big bucks. Also, there’s the issue that Betances has been overworked the last few seasons. Will he hold up? The team is probably better off waiting at least another year before considering this.

Michael Pineda:

It’s hard to make a case for one of the biggest pitching enigmas in the game. But hear me out. Unless some of these young pitchers break through this season, the Yankees 2018 starting rotation looks bleak. The team’s current pitchers with guaranteed spots in the rotation for this upcoming season could all be gone for the next one. I think we can agree that the Yankees shouldn’t extend Sabathia (though one-year deals should be looked at) and Masahiro Tanaka will be expensive and risky. Pineda could probably be extended at a discount given his erratic performance with the Yankees, and he’s at least shown both flashes of brilliance and a decent health record over the last two seasons. It’s a hard decision but I’d consider adding another couple years at a relatively affordable rate (maybe two years/$20-$25 million which is more annually than his arbitration payouts).

Masahiro Tanaka:

I know I just said he could be expensive and risky given health concerns but Tanaka is a tough arm to replace. Assuming he plans to opt-out after this season, the Yankees could look to try and extend him now (of course they’d need to do better than the 3 years/$67 million left on his contract), in the hopes of paying less than they would have to in order to resign him as a free agent. If the Yankees have any desire to re-sign him when he opts out and hits free agency, they should extend him now. The risk is he gets hurt this season. The upside is they save millions of dollars by extending him early.

Gary Sanchez:

Yes, he’s a long way from free agency. Why would the Yankees even consider this? But if Sanchez puts up a big year, his value is going to skyrocket. This is a risky move with someone who has only a third of a season under his belt but signing him to a big extension now could save the Yankees large amounts of money down the road. Each season he puts up big numbers will inflate his potential price further. Just look at Giancarlo Stanton or Mike Trout. Extending Sanchez to a relatively affordable deal now could help them avoid being trapped into a situation of paying a catcher a mega-contract (especially given how he’ll probably be seriously popular in New York, trapping the Yankees further should be hit free agency). I would probably wait another year on this, but I wouldn’t wait much more.

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