Assuming you’re not merely viewing things thru the prism what a huge bummer it is for the Cubs, it would be slightly hysterical to claim the Yankees’ signing of RHP Masahiro Tanaka to a 7-year, $155 million is an even worse investment than the recent truckload of cash foisted upon the oft-injured Jacoby Ellsbury. But not so crazy, however, to point out (as The Read Zone’s Brian Mangan has done) that Tanaka has the right to bail on the contract after 4 years (“essentially, the Yankees just signed Tanaka to a four year, $108 million deal with a unilateral player option for 3 more years at $67 million”)

If Tanaka is excellent, then he will opt-out after four years like Alex Rodriguez did and demand an enormous and expensive extension. If Tanaka is bad, the Yankees will have paid him the second-richest deal in history and gotten no return, and Tanaka will be entitled to a three year, $67 million extension for nothing. It’s a deal with limited upside and $108 million downside.

A lot of Yankee fan friends are telling me that the money doesn’t matter – which is a fine argument to make, even if I don’t believe that it’s true. If so, disregard this article because there is no reason to analyze the value of the deal.

However, if money doesn’t matter, then why don’t the Yankees have Robinson Cano locked up so that he could finish his career as a Yankee? Robinson Cano posted wins above replacement (WAR) of 6.4, 5.3, 7.7, and 6.0 over the last four years, and the Yankees let him walk because they didn’t want to pay him $24 million per year over the next ten years (and remember, $24 million in 2023 is significantly less than $24 million today).

Is Tanaka going to be better than Cano? Unlikely. And even if Tanaka turns out to be better than Cano, the Yankees will be losing him in four years anyway (or be required to sign him to an onerous extension).