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Top 3 Worst Free Agent Signings in Yankees History

Fresh off another ALCS exit, the New York Yankees turn their attention to the offseason, where the most significant priority will be re-signing star free-agent slugger Aaron Judge.

While Judge has earned a substantial payday, free agency has not been kind to the Bronx Bombers, with several big money deals turning into colossal nightmares.

Here are the worst of the worst, starting with 2004’s “prized” acquisition.

3) SP Carl Pavano – Four Years, $39.95 Million

Pavano enjoyed a career season in 2004 while a member of the Florida Marlins, posting an 18-8 record and a 3.