30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
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29. Gary Sheffield, 2003: Three Years, $36-38 Million

Language surrounding Sheffield's Yankees deal at the time is confusing; Peter Gammons reported it as "between $36 and $38 million" at the time, while other outlets considered it to be $39 million.

Regardless, he's slotted in the right place. Don't question it.

Sheffield did nothing but mash after coming over from the Braves, adding intimidation and swagger to a somewhat stale Yankee lineup while drilling 36 and 34 homers in his first two seasons in the Bronx. By 2006, he was breaking down somewhat, and found himself dealt to Detroit for a package highlighted by ... Humberto Sánchez? It felt like a big deal at the time!