3. Kei Igawa (2007-11)
Following the conclusion of the 2006 season, the Boston Red Sox caught the baseball world’s attention by paying over $100 million (about half of the price was for negotiating rights) to sign highly-regarded Japanese star pitcher Daisuke Matsuzaka.
Not to be outdone, George Steinbrenner made his own move in the new Japanese market by signing Kei Igawa. After posting the winning bid of $26 million, the Yanks signed the lefty to a five-year, $20 million deal. But entering the Japanese market was an experiment and a risk for the organization.
Unfortunately, Igawa flopped in New York. He experienced control problems and went back and forth between the Yanks and Scranton Wilkes-Barre RailRiders in 2007. Igawa was 2-3 with a bloated 6.25 ERA (in 14 games and 12 starts) for the Bombers that year. In 2008 he pitched only two games and was impossible to trade.
Igawa spent the remainder of his contract being paid to pitch in the minors. After dropping a total of $46 million, the contract came to an end in 2011. He pitched in just 16 games and logged a 6.66 ERA and a 1.76 WHIP. It’s no consolation that Igawa is the all-time wins leader in Scranton/WBR’s history.
We’re just not sure why the Yankees saw this contract all the way through.