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Looking down the road, the Yankees will need to start extending some key players before they hit free agency -- waters that those players might want to navigate to find a new team.

So, while the Yankees have a roster capable of winning a World Series at the moment, GM Brian Cashman will be doing everything in his power to make sure that remains intact. To do so, it requires some big decisions.

We've already taken a look at Gary Sanchez's situation. Now let's examine Masahiro Tanaka, who is set to hit free agency after the 2020 season...

CONTRACT: Tanaka is in the final year of the seven-year, $155 million deal he signed with the Yankees in 2014 when he came over from Japan.

Why should Tanaka stay?

Consistency. That's what Tanaka brings to the Yankees pitching staff.

Since he came over in 2014 (an All-Star year), New York has known exactly what to expect when he gets the ball every fifth day. Of course, there are some struggles and bad outings every now and then. But Tanaka has mainly been someone the Yanks can trust, with a career 3.75 ERA over 164 games and 1,006.1 innings on the bump.

The postseason is where Tanaka truly thrives, though, and that will play a major part in keeping him aboard. He has eight starts dating back to 2015, and owns a 1.76 ERA (46 innings pitched). He knows how to set the tone on the mound, no matter if it's a home or away matchup. The Yankees truly covet that aspect of Tanaka's game, as he seems totally unfazed in the biggest of moments.

All Tanaka has known is the Yankees since his much-anticipated transition to MLB. He could have been a Dodger or a Red Sox, but he chose New York because he felt it gave him the best opportunity to win a World Series title. The Yankees have been close to fulfilling that goal, and Tanaka could get that this year -- this is the best roster he's been a part of thus far.

He's as loyal as they come, a great teammate, and an uber-competitive spirit whenever his cleats touch the rubber.

Why should Tanaka go?

The partially torn UCL in his right elbow has been an issue for several seasons. Tanaka hasn't needed surgery, or had any real issues with it. He still continues to pitch with that out of sight and, what looks to be, out of mind.

But the Yankees certainly don't have that out of mind, and it could cost him a new deal that he's looking for.

Tanaka will be turning 32 during the 2021 season, and we all know what starts to happen when most players reach that 30-year-old mark. With Tanaka having a pre-existing condition that the Yankees will need to continue worrying about, signing a longer-term deal would be very risky if the team believes that UCL injury could eventually result in Tommy John surgery.

That should be Cashman's main concern when mulling over what to do with Tanaka.

What's the right move?

If you can trust the UCL will continue to hold itself together, the Yankees definitely should be extending Tanaka. Just take a look at the rotation now: you have Gerrit Cole as the ace, Luis Severino set to come back from Tommy John surgery, James Paxton (we'll get to him in the next version of this series), and then Tanaka. Having someone like him eating up innings while sitting in the middle of the rotation is a great asset for any team.

At this point in his career, Tanaka shouldn't get close to that $22 million he was averaging over his first deal in his prime. New York certainly realizes that, but players always bet on themselves -- especially when free agency hits. Tanaka was deliberate in his choice of the Yankees in his first taste of it, so he could do the same thing again.

If the price tag is too high, the Yankees should be focusing on the younger Paxton if they have to choose one of them -- despite Tanaka's long tenure with the team. But after six seasons and no ring, Tanaka may just want to be in the best position to acquire that. The Yankees would be an obvious choice there, so maybe money won't be the main goal.

So, in the end, a shorter term deal -- three or four years -- that is front-loaded to give Tanaka a bigger chunk of money in the immediate would be ideal for the Yankees. Cashman can then worry about others like Aaron Judge and Gleyber Torres down the road when they are expected to get extensions, knowing Tanaka won't cost too much in those seasons.

Tanaka is a valuable piece and someone Yankee fans have come to love. It's only right for him to continue his career in the Bronx.

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