When the Yankees signed Masahiro Tanaka to a seven-year $155 million contract, it was the best thing they could have done at the time. He was dominant, young, and healthy. Then when the full terms were released, Tanaka had an opt-out clause after the 2017 season and I was pretty unhappy about it. I've never much cared for player-controlled opt-out clauses because it has the team taking on all the risk–if he's good, he goes, if he's bad or hurt, you're stuck with him. Recently, the market has changed a bit and now, as long-term contracts were hitting their tipping points at eight-year deals for pitchers, opt-out clauses were introduced as a way to prevent things from getting any crazier. Now, I kind of like these opt-out clauses that let players collect their top dollar value, but don't put teams on the hook for their declining years. It all works out, as long as the team has a plan.
Back when CC Sabathia first signed his seven-year contract with the Yankees, he was under control for three years before an opt-out clause would allow him to leave after the 2011 season. When CC leveraged his contract early in the offseason, the Yankees rotation was in shambles–A.J. Burnett had another difficult year, Phil Hughes had fallen apart, Ivan Nova was still a mystery, and Andy Pettitte hadn't come out of retirement yet. At that point, the Yankees had no other alternative but to re-up with Sabathia and tack on another two years to his deal. It looks terrible now, but at the time CC was a Cy Young-caliber pitcher and the only thing holding the pitching staff together. Now I feel like we're heading toward another situation like this with Tanaka after the 2017 season.
In a matter of two seasons, the Yankees rotation will be gone. CC Sabathia's contract will finally be over, Nathan Eovaldi and Michael Pineda will hit free agency for the first time, and Masahiro Tanaka will be able to opt out. The only starter they would (hopefully) have locked into the rotation by then is Luis Severino, leaving the Yankees with even less options than they had before the 2012 season. New York decided not to spend money on any of the big free agent pitchers this offseason, and while it's one thing to try and avoid more bad free agent contracts, they still need to add some kind of proven talent in the near future.
The problem with their decision to wait until they have money coming off the books–Carlos Beltran and Mark Teixeira will both be free agents after the 2016 season–is that there is no one worth signing next offseason. The free agent pitching class next winter is essentially Stephen Strasburg and a bunch of closers. Sure, they could be planning to go after Strasburg, but that's asking for a lot to go right in the next year. If they lose out, they'll have no one to carry the rotation further down the road. Then, after 2017, when Tanaka can leave, the Yankees could go after Jake Arrieta, Tyson Ross, and, like, Jamie Garcia? Free agency isn't what it used to be, so it might be worth keeping an eye on Pineda and Eovaldi to see if they're worth keeping around.
If they don't sign a starter in the next three offseasons, the farm system might not be the place to look for sure-fire alternatives. Right now there are no starting pitching prospects in the upper minors, and guys like James Kaprielian and Ian Clarkin are still a little too far away to plug into rotations yet to come. The Yankees went college-heavy in the last few drafts in order to get as many pitchers to the big league level as quickly as possible, but what are the ceilings for these players really going to be? As much as I appreciate the foresight and love the idea of homegrown players succeeding, you can't have a rotation filled with backend starters and hope to win. They need a sure thing to relieve some of the question marks they have had to deal with recently.
Of course, there are two major differences when it comes to extending Tanaka. He's two years younger than Sabathia was when he was able to opt out, so a 28-year-old starter might actually be worth extending in a way a 30-year-old pitcher might not be in today's market. There's also Tanaka's elbow, which presents itself as a major ticking time bomb. The Yankees don't exactly know when it will tear. Maybe it happens before the opt out, maybe after, but the health of his elbow will be a major deciding factor as to whether he opts out and whether the Yankees extend him. The delicate situation that this could turn into makes it even more important that the Yankees get it right this time.
Maybe Brian Cashman will continue to make more trades that will produce the next Pineda or Eovaldi without giving up too much in return. Then at least we'd know there was a plan. That they've thought about this well in advance and are prepared for when it happens again. Yes, there probably is a plan, even if we can't see it currently, but it would be nice to see some actions being taken toward that end goal. It's fine if Tanaka opts out, but what they can't do is fall at his knees like they did with CC, especially when his elbow could go at any time. The Yankees need a clear contingency in place so they can bring him back on their own terms or not at all because all the work they have done recently won't mean anything if they relive past mistakes again and again.