30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
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17. Hideki Matsui, 2005: Four Years, $52.5 Million

After a successful first contract in the Bronx, the Yankees brought Matsui back for more after the 2005 season -- and don't win the 2009 World Series without him, either.

His Yankee career probably (sadly) ended at the exact right time, riding a significant high into the aging curve in Anaheim.

Matsui wasn't a 50-homer slugger in New York like he was with the Yomiuri Giants, but he was a stunning natural hitter, and quite possibly the "clutchest" Yankee of the decade, as unquantifiable as that title is. In 2009, he hit .303 with 8 homers and 65 RBI with RISP and .240 with 15 solo bombs with the bases empty. During that year's World Series, he wrapped his time in the Bronx by hitting .615 with three homers, despite being unable to DH and start on the road in Philly.

All-time Yankee.