30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
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8. Masahiro Tanaka: Seven Years, $155 Million

Masahiro Tanaka's offseason contract, which capped the Ellsbury/McCann/Beltrán ill-fated spending spree, has universal approval to this day.

Though Masa suffered a partial UCL tear during his dominant first season in the Bronx, the injury ultimately never required Tommy John surgery, and he remained healthy long enough to become a postseason legend in 2017 and 2019.

His playoff reputation was only pricked once with fans in the stands -- on short rest by the 2019 Astros in Game 4 of the ALCS, a few days after his greatest masterpiece, a Game 1 six-inning one-hit shutout.

Unfortunately, he was rocked twice in the 2020 postseason (once when a rain delay interrupted his start in Cleveland), and has pitched in Japan the past two seasons. Not as dominant a regular-season Yankee as once was forecast, but objectively a good buy (especially considering his offseason still has the Ellsbury stink on it).