30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
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22. Kei Igawa, 2006: Five Years, $20 million ... Plus $26 Million Posting Fee. $46 Million Total Cost.

Perhaps Igawa doesn't technically belong this high, but it just ... felt right to discuss him here, considering the total money committed to his purchase would've been better spent in a bonfire.

Igawa was thought to be a high-upside No. 4 starter at worst when he came over from the Hanshin Tigers. Instead, he was more like a low-upside No. 9 starter. In two seasons where he made big-league appearances, Igawa subtracted 0.5 WAR from his Yankees teams, and wound up exiled to the high minors for years 3-5 of his contract.

Igawa became the veritable Mayor of Scranton, but that probably wasn't worth $46 million of the Yankees' money. It's the second-worst purchase the team has ever made, right behind the time they paid Kevin Brown $15 million to smash them in the knee with a wrench.