30 biggest free agent contracts in New York Yankees history

The dollar amounts that the New York Yankees, accused of "buying championships" throughout the '90s, have actually spent over the years may surprise you.

Or, more accurately, they'll warp your mind when you realize how much the game has changed since the mid-1990s.

What used to be an exorbitant free agent sum now misses the list of New York's top 30 signings, by total dollar value, entirely. Kenny Rogers and David Cone, who both signed during the 1995-96 offseason for $19.5 million (four years for Rogers, three for Cone), have seen their earth-shattering deals eclipsed by pedestrian modern contracts like Adam Ottavino's three-year, $27 million pact from 2019.

This free agency deep dive into the Yankees' behaviors is enlightening, and also helps illuminate how much cash it took to keep the Core Four together over the years.

Richest Contracts in New York Yankees History

HONORABLE MENTIONS:
Rafael Soriano, 2010: Three Years, $35 Million
JA Happ, 2018 (lol): Two Years, $34 Million
Randy Johnson, 2005: Two Years, $32 Million ($57 million total obligation, thanks to AZ)
Jose Contreras, 2003: Four Years, $32 Million (El Duque cost just $6.6 million over four years pre-1998)
Roger Clemens, 2007: One Year, $28 Million prorated down to $18.7 million for partial season (cool)
Danny Tartabull, 1992: Five Years, $25.5 Million
Dave Winfield, 1980: 10 Years, $23 Million (!!!, what)
Hideki Matsui, 2002: Three Years, $21 Million

So, what are we waiting for?! Let's spend as much as fans wish Hal Steinbrenner would dole out in one offseason, all within the confines of a single article!