With a looming opt-out featuring uncertainty for ace Masahiro Tanaka, the New York Yankees find themselves in a little pickle. 

New York Yankees’ starter Masahiro Tanaka is everything a team wants in an ace.

Last season, the righty pitched in 199.2 innings, the most by a Yankee since Hiroki Kuroda in 2014, and finished with the third-best ERA (3.07) among qualified American League starters behind Aaron Sanchez of the Toronto Blue Jays (3.00) and Justin Verlander (3.04) of the Detroit Tigers.

According to FanGraphs, Tanaka also owned the ninth-highest win probability added among starters in major league baseball, assuredly securing his spot as a Top-10 starter in the sport.

However, instead of talking about what could be an incredible upcoming campaign for the 28-year old, when Brian Cashman announced that he hasn’t spoken to his ace about a contract extension, it sparked a conversation concerning a potential opt-out.

For those who aren’t aware, Tanaka has four years, $89 million left on his seven-year, $155 million contract signed in 2014, and there is an opt-out option following this upcoming season.

While many believe Cashman could pull off an Aroldis Chapman-like deal, — trade Tanaka for a stockpile of prospects at the deadline and re-sign him next offseason — they are really in a predicament with this contract.

Because, no matter how 2017 plays out for Tanaka, the Yankees could get the wrong end of the stick in every scenario.

Let’s say Masahiro recreates his 2016 performance and continues to be a “Hiro” for New York. He’ll certainly walk away from the final three years of his deal, forcing the Yankees to pay a 29-year old more than his current value ($22 million) and presumably six or more years.

Even if he just stays healthy and perhaps has an OK year, then he may opt out when he’s allowed or even settle for a contract extension — just like CC Sabathia before 2012.  

In that case, just use Sabathia as an example.

New York gave their 31-year old ace a five-year, $122 million extension that would carry into his age 36 season, after going 59-23 with a 3.18 ERA in his first three years in pinstripes.

Since then, the big lefty is 47-45 with a 4.25 ERA and will make $25 million in 2017 for a pitcher he was six years ago.

Throughout Tanaka’s first three years, he owns a 39-16 record with a 3.12 ERA but, like Sabathia, an extension would carry him into his mid-30’s for what could end up being $25+ million a season.

Yes, CC had a renaissance in 2016, but even that version of the southpaw isn’t worth what he was during his first three years in the Bronx.

If you think that sounds like a dangerous comparison, did you forget about Masahiro Tanaka’s partially torn ulnar collateral ligament?

That could tear further, requiring Tommy John surgery and forcing him to adhere to his contemporary contract which means: the Yankees are firmly fastened into a massive deal and won’t even get results.

Is there any way this could work out for New York? Frankly, no. Opt-outs rarely workout for the team that hands them out, and this situation is no anomaly.

Of course, they are banking on Tanaka to have a solid year. I mean, just look at that rotation. And in 2018, with the enigma of Michael Pineda being due for free agency, the only guaranteed starters on the roster would be Luis Severino, Chad Green, Luis Cessa, Bryan Mitchell, Adam Warren and some kids.

Not fitting.

That being said, it makes sense for the Yankees to sit down with Tanaka’s party and settle on an extension — despite the risk. As mentioned, however, Cashman would rather wait for his ace’s decision rather than jump on an extension because of risks not working out for the 20-year GM in the past.

The problem is, though, they’ll spend money on starting pitching over the next couple of offseasons anyway. Like I said, they have no guaranteed depth beyond Tanaka.

If he walks, he’ll join a market that could feature the likes Yu Darvish, Jake Arrieta, Johnny Cueto and more. And even with the importance of relievers in the new day in age of baseball, starters will continue to get a big fat paycheck.

Basically, if you were rooting for the front office to avoid a sequel to Sabathia’s contract blunder, New York may have no choice but to take the same gamble this time around.

They can do nothing but root for him to have a solid 2017 campaign in hopes to make a run not many are expecting. It will cost them, but they’re certainly damned if they don’t, and may be damned if they do.