Yankees worst free agent contracts ever handed out

SAN DIEGO, CALIFORNIA - JULY 3: Jacoby Ellsbury #22 of the New York Yankees slides as he scores during the ninth inning of a baseball game against the San Diego Padres at PETCO Park on July 3, 2016 in San Diego, California. (Photo by Denis Poroy/Getty Images)
SAN DIEGO, CALIFORNIA - JULY 3: Jacoby Ellsbury #22 of the New York Yankees slides as he scores during the ninth inning of a baseball game against the San Diego Padres at PETCO Park on July 3, 2016 in San Diego, California. (Photo by Denis Poroy/Getty Images) /
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(Photo by J. Meric/Getty Images)
(Photo by J. Meric/Getty Images) /

Kei Igawa

Yet another pitcher on that 2007 roster. Kei Igawa was another name in a long list of former Japanese All-Stars trying their hand on American shores. His signing in 2006 was a knee-jerk reaction to Boston outbidding and claiming coveted Seibu Lions pitcher Daisuke Matsuzaka.

Igawa was dominant in 2003 (20–5 record, 2.80 ERA) for his Hanshin Tigers, but his play fell off consequently in 2004 and 2005. He was even sent down to the minors for a brief period and was heckled by fans.

He had strikeout ability, but control issues plagued him. Despite the warning signs, the Yankees signed Igawa to a 5-year, $20 million deal (not including the $26 million posting fee). Igawa would go on to appear in just 16 games for the Yankees, posting a subpar 2-4 record with an ERA of 6.66 (spooky).

Igawa was thus cast to minor league purgatory, becoming a player earning about 130 times the average farmhand. Igawa even set the Scranton-Wilkes/Barre record for most wins.

When one dives a bit more, Igawa becomes a curious and even sympathetic case. Ian Pennington of the New York Times detailed his journey and what brought Igawa to the minors. Igawa always had the work ethic and willingness to adapt, but he was simply outmatched in a land and environment where he was unfamiliar.

But at the end of the day, he will be remembered by what Brian Cashman admitted. “It was a disaster. We failed.” Hey, at least Igawa had a really high rating in MLB ’07 the Show, higher than Daisuke, even.