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The Yankees could explore the Aroldis Chapman route with Masahiro Tanaka

If he’s having a typical Tanaka season but the Yankees are struggling, the Yankees could explore trading their ace and then re-signing him in the offseason.

Tampa Bay Rays v New York Yankees
“You want me to throw this?”
Photo by Jim McIsaac/Getty Images

One of the much-discussed topics of the offseason has been the Yankees’ rotation, or lack thereof. In addition to having rotation question marks going into this season, the Yankees have virtually no guaranteed pitching after this season. Michael Pineda, CC Sabathia will be free agents after the season, and most importantly Masahiro Tanaka has an opt-out that will likely have him join the market as well.

Back in December, PSA’s Jason Cohen wrote about how the Yankees need to do what it takes to keep Tanaka beyond this year. One of the options suggested was the team offer him a contract extension similar to what they did with Sabathia back in 2011. If the Yankees wanted, they could start negotiations with him now and try and add some tack on years in order to get him to stay. However, there’s a very good chance that Tanaka and his agent decide they want to test free agency.

Sure nothing is official yet, but as long as Tanaka is healthy him opting out is guaranteed. And if he’s going to hit the market anyway, the Yankees could choose to do something similar to what they did with Aroldis Chapman last season. It’s a bit more difficult considering Tanaka has a full no-trade clause, but it’s not out of the realm of possibility.

Say the Yankees are having another season similar to 2016, which is a real possibility, then they could ask Tanaka to waive his no-trade clause so they could ship him to off a contender. Then, next winter, they could enter the bidding war for him and bring him back. Sure there’s a lot of things that need to happen, but if Tanaka is having another typical Tanaka season and if the team is struggling to even hover around .500, why not?

Pitching is always a hot commodity. Whether it’s at the trade deadline or in the winter, teams are always looking for more pitching. And teams would definitely fall in line for an ace like Tanaka. If so, Brian Cashman can use his ninja-like skills to pull off another masterpiece similar to Chapman. While the Yankees farm system is top-notch, there’s always room to improve, especially if they were to acquire any top-tier pitching prospects in return.

Joel Sherman of the New York Post just wrote that if Tanaka has an ace-like 2017, it would put the Yankees in a bind. However, I think if he’s having an ace-like 2017, it could actually benefit the Yankees. Sure if the Yankees are right in the thick of things, they’re not going to be selling off assets, but the chances of that are low. And while Cashman had a tough time convincing Hal Steinbrenner to sell last season, he did end up getting the job done with the promise of a brighter future.

Cashman almost assuredly didn’t convince Steinbrenner that the Yankees would be instant contenders right away in 2017, but more likely, he convinced him to believe in his process. That it’s worth it to “sell” now and let these prospects develop so they could become contenders in a few years. And if the team is again struggling, there should be almost no reason for Hal Steinbrenner to say no to a trade, especially if it were done in the context of “we could bring him back when he opts-out.”

That’s assuming that they even will try and bring Tanaka back. Outside of the Chapman deal, Steinbrenner has been pretty hesitant to spend big money the last few seasons. Or the team could potentially be gearing up for another upcoming big name free agent like Yu Darvish or Jake Arrieta. If that’s the case, then why just let Tanaka walk for nothing? Granted they’ve gotten great value out of him for 3 years, but why not get something back in exchange?

Sure the Yankees are the only MLB home Tanaka has known. Keeping him throughout the year could make it easier for them to re-sign him. The Red Sox tried a similar strategy with Jon Lester a few years back and he ended up signing with the Cubs. Lester said the trade from the Red Sox to the A’s actually made the decision to sign with the Cubs easier. So it’s no guarantee that if the Yankees go this route, it would work. But then again, if Tanaka elects free agency, there’s no guarantee he’d re-sign with the Yankees anyway.

Everything in this business is a gamble, and this wouldn’t be any different. So depending on where the team is come July, it wouldn’t be surprising to see the Yankees approach Tanaka about waiving his no-trade clause.