30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
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18. Jorge Posada, 2007: Four Years, $52.4 Million

This legacy contract carried Posada to the end of his Yankees career, when he walked away after the 2011 season as a catcher/DH, sinking below the league average in OPS for the first time since 1999.

How Posada hasn't gotten more Hall of Fame consideration is stunning -- oh, wait, no it's not. He got automatically dinged by the voters for being a Yankee. Never mind, not stunning. Normal.

This contract, alongside Jeter's, Mo's, and a number of one-year deals for Andy Pettitte, helped keep the core together for one more title run in 2009 -- a season where Posada turned back the clock and hit .285 with 22 bombs and a 125 OPS+ as a 38-year-old.