From Derek Jeter to Alex Rodriguez: Ranking the Richest New York Yankees Contracts of All-Time 

The Yankees have built a longstanding reputation and throwing around the big bucks when they want a certain player. But which contracts are among the richest in franchise history? Here’s the top of that list. 

Gerrit Cole: nine years, $324 million 

Cole has a record-breaking deal of $324 millions with New York Yankees for the next nine years! 

Giancarlo Stanton: 13 years, $325 million 

Giancarlo Stanton is a player who has a $325 Million contract, but it's spread over 13 years, so that's why he is not on the top of the list.   

Alex Rodriguez: 10 years, $275 million 

Speaking of getting a contract extension with the Yankees at an opportune time, here’s Alex Rodriguez. Instead of opting into the rest of his then-record $252 million deal, he opted out and eventually negotiated an even bigger deal after his age-31 campaign. 

Derek Jeter: 10 years, $189 million 

Could there have ever been better leverage for a long-term extension than what Derek Jeter had following the 2000 season? He had just five full years in the big leagues, but it included one Rookie of the Year Award, three All-Star selections, and three top-10 AL MVP finishes. 

Mark Teixeira: eight years, $180 million 

This was just another part of the Yankees’ offseason spending spree that helped lead to a 2009 World Series title. New York had just finished a long and expensive contract with Jason Giambi (which we can see above). Naturally, they went out and secured another first baseman for the long haul in Mark Teixeira.

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