The last “real” free agent SP the teamed signed has been one of the best value decisions of the decade

The offseason has barely begun, with the GM meetings taking place next week and a whole bunch of MLB clubs starting their internal hiring processes. Yet in Yankeeland, we’re already thick in the debate about what the team should do this winter, specifically with respect to the two star starting pitchers on the free agent market.

CC Sabathia and Giancarlo Stanton have already voiced their desire for the Yankees to sign Gerrit Cole, or Stephen Strasburg, or both of them. We’ve heard both sides of the debate before, last year around Patrick Corbin, two years ago when Yu Darvish was a free agent, and on and on. The position of the Yankees has been the same; the team hasn’t signed a “real” free agent - a pitcher that wasn’t on the team at the end of the preceding year - since 2014.

And what a signing that was, when the Yankees landed 26-year-old NPB star Masahiro Tanaka. New York inked Tanaka the old fashioned way, by offering a player the most money. It wasn’t a value play, and there wasn’t talk about dollars per WAR. The team just bid the most and got the guy they wanted.

Since then, Tanaka has legitimately been one of the 20 or so best starters in the game:

He has been in the top 20 in fWAR, top 25 in innings pitched over the last five seasons and K-BB%, and of course has the third-best postseason ERA in baseball history. That’s a pretty good resume for a guy who hasn’t quite been anointed an “ace.”

If you’re one of the new kinds of Yankee fans - or Brian Cashman himself - and obsessed with maxing out “value,” the news is even better. Those 18 wins Tanaka has accrued, if you assign a relatively conservative $8 million per win, means he’s been worth about $15 million more than the money he’s been paid. That’s a pretty good return for any club.

There’s a lot of risk in free agent deals - they’re given out to guys that are a little older, probably with a fair amount of mileage on the arm, and often come along with accouterments like no trade clauses that limit the yearned-for “roster flexibility.” And yet sometimes, it just works out. Sometimes, signing the big name to the big contract is the right move.

Tanaka was the right move, he’s been worth $15 million. Max Scherzer was the right move, he’s been worth more than a hundred million dollars to the Nationals. The big free agent signing the Yankees made before Tanaka was CC Sabathia, who also proved his worth. This winter provides another opportunity for the Yankees to sign the big name to the big contract, and once again all signs point to it being the right move.

Gerrit Cole is fresh off a two-season run as dominant as any pitcher of his era. His 2019 was so stellar, if he started every at-bat down 1-0 in the count, he would have finished with the third-highest strikeout rate in baseball. He’ll cost a truck load, but he’s the absolute best in the game right now.

Stephen Strasburg is coming off a dream October, and a 200-inning season that would have had him head and shoulders above any Yankee starter. He’s a post-hype star at this point, and he’s still worth the big deal.

Free agents carry risk, but the right one can be all the difference in October, and come out of the wash being worth more than the deal. Tanaka was one, and he was the last one the Yankees have enjoyed. It’s time for them to make the splash again.