In the aftermath of the Aroldis Chapman signing and the Yankees’ general frugality this offseason, Kei Igawa of all people popped into my head the other day. In a time and place that seems especially far away from the present day, the Yankees spent a total of $46 million to bring Igawa over from Japan in December of 2006. Given the Yankees’ penny-pinching ways this offseason, doling out this much cash to an unproven Japanese pitcher with no real record of sustained success seems unfathomable.

Here’s what Igawa has given the Yankees in the Majors during the first three years of this deal (by the way, he’s incredibly signed for two more seasons!):

I remember his one outing against the Tigers in 2008. 13 hits in four innings! I went over to my brother’s place to watch that game and we couldn’t stop crying from the moment Igawa took the hill, due to a combination of agony and laughter.

And here’s what Igawa has done in parts of three seasons at AAA:

A career FIP over 4 in the minors. Sure paints a pretty picture, doesn’t it? I guess $45 million just doesn’t buy what it used to.

While Brian Cashman takes his share of crap for Carl Pavano, at least there was something of a track record involved, and it seemed like a good idea at the time. I think Kei Igawa has a strong case for worst free agent signing in Yankee history. Igawa had a questionable track record at best, and the signing was clearly a knee-jerk reaction to Boston landing Matsuzaka.

Just imagine if the Yanks hadn’t blown over $40 million on a guy who will pitch the remainder of his contract in triple A. Not that they necessarily needed Chapman, but without the Igawa debacle perhaps the Yankees feel a bit more confident about venturing back into international waters. They’d at least have had the money to strongly consider doing so (of course, assuming that it wouldn’t have gotten spent on something else in the last three years, which in all likelihood it probably would have) with enough left over to bring Johnny Damon back as well.

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