For years we had heard that the Yankees don't do extensions. They will sign free agents to large deals, but not their own players to new contracts before their old ones run out. It was an odd policy that likely cost them Robinson Cano, but they since broke down the doors to the contract extension when they signed Brett Gardner to a four-year, $52 million contract to begin in 2015 and suddenly everything was different. Unfortunately, they also decided not to extend David Robertson and it meant he would leave in free agency at the end of the season. Now a new crop of young talent is coming in and it's time to consider which of them the Yankees should sign to affordable contracts before they hit free agency.
After what they saw from Michael Pineda when he returned from injury, the Yankees need to start considering an extension for the 26-year-old. He's under team control for another three seasons, not scheduled to hit free agency until after the 2017 season. Since the shoulder injury will keep his arbitration earnings down and be a red flag for any longterm deal, I think it makes a lot of sense for both sides. New York will have a young frontline starter under a team-friendly deal and Pineda would have security in case his shoulder doesn't hold up for the length of his career.
Along with Pineda, the Yankees should also consider an extension for newest Yankee starter Nathan Eovaldi. Obviously, it's way too early to give him one now, but the organization believes that they can harness his abilities and turn him into an effective mid-rotation arm. Maybe he doesn't end up at the top of the rotation, but if he can throw 100 mph and be effective, he's worth keeping around, especially if it's lower than market value. We'll have to see how Eovaldi does in his first season in the Bronx before seriously considering some kind of deal, but 2015 is the first step.
A few other Yankees might not need to be locked up any time soon, but it's worth starting to consider such a longterm arrangement, just in case. Right now there's no reason to worry about losing either Didi Gregorius or Dellin Betances, mainly because they are both under team control until 2020 and make the league minimum in 2015, but there are other concerns as well.
It's entirely possible that Gregorius never turns into a full-time, starting shortstop. While his bat as a whole is questionable, it has yet to be seen whether or not he can hit left-handed pitching at all. If he can't and his production doesn't improve at the plate like the Yankees hope it will, then there's no reason keeping him around on a more expensive deal if he's just going to be a glorified utility player. We will have a few years still before we need to worry about whether or not Didi is worth keeping at under-market value.
When it comes to Dellin Betances, the Yankees need to be patient. He had such a good season that it's highly likely 2015 will be a disappointment by comparison, however, it all comes down to how big of a let down it will be. Betances was one of the most valuable relievers in baseball thanks to his abilities, but it was his league-minimum salary that made him worth so much to the team. There's no rush to have the Yankees pay more for a reliever if they don't have to, so he has another few years before he's arbitration eligible for the first time in 2017. At that point, if he's still who he is now, it could be a good idea to sign him to an extension so they don't have to pay top dollar for their closer. Unless, of course, they have another rookie waiting in the wings by then.
I would have identified Ivan Nova as an extension candidate this offseason if it wasn't for the fact that he's a complete unknown right now as he makes his way back from Tommy John surgery. We need to see if he's even the same pitcher he was before, and whether that's the league-leader-in-hits Nova or the second-half-of-2013 Nova. With two years of control left, we're running out of time to find out, so a successful 2015 season, and I mean unexpectedly better than we all hoped for, could make him an extension candidate next offseason. It's possible that the cautious Yankees might still not consider that enough time to make a longterm commitment, but we just have to see.
If the Yankees are no longer interested in signing players like Jon Lester and Max Scherzer to big contracts, then they're going to have to start retaining their own players and this is how to do that.