3. New York Yankees
Until recently, Gerrit Cole’s nine-year, $324 million contract signed prior to the 2020 season held the franchise record. Judge’s nine-year, $360 million deal blew that away, both for raw amount and AAV ($40 million).
The Yankees, of course, have a long history of featuring the richest players, going back to that Ruth contract in 1930. They ushered in the free agent era late in 1974, luring Catfish Hunter away from the Oakland A’s by ponying up the then-fantastic sum of $3.25 million over five seasons.
The current owner, Hal Steinbrenner, and his long-time owner father, George — often in concert with long-time general manager Brian Cashman — have over the years dispensed so much free agent cash that the following statement is true: Considering the 180 richest free agent contracts ever handed out in franchise history, not one was paid by an owner named something other than Steinbrenner, and only 14 percent were executed by a GM other than Cashman.
The most expensive of those 25 was a $25.5 million contract given by Gene Michael to Danny Tartabull three decades ago. It now ranks 28th richest on the franchise list.
From a pure dollar standpoint, the franchise’s glory days came more than a decade ago. In a span of 13 months in late 2008 and 2009, the following occurred:
- George Steinbrenner resigned Alex Rodriguez to a 10-year, $275 million contract that was supposed to run from 2008 through 2017. Suspended in 2014, Rodriguez abandoned the final year of the deal and retired at the end of the 2016 season.
- Then Hal Steinbrenner resigned C.C. Sabathia to a seven-year, $161 million contract from 2009 to 2015.
- Finally, Hal signed Mark Teixeira to an eight-year, $180 million deal. In concert, those three signings played a large role in the winning of New York’s last World Series in 2009.