Over the last 20 years, the New York Yankees have claimed five World Series championships, seven American League Pennants and five AL East titles. The success of the Yankees has come in large part from the homegrown talents of the “Core Four.”

Derek Jeter, Mariano Rivera, Jorge Posada and Andy Pettitte were certainly the faces of the Yankees dynasty—and arguably the most eccentric part of the success the Yankees had. However, the shrewd moves in free agency are what helped build this team into the force it has become.

Over the past two decades, there have certainly been some great free-agent signings by Brian Cashman, as well as some bad ones. Guys like Mark Teixeira and CC Sabathia have certainly contributed to recent success for the team, but what about the guys in the 1990s? What about the guys who helped the Yankees win four championships in five years? What about guys like Orlando “El Duque” Hernandez and David Wells?

This article will break down the Yankees five best free-agent signings of the past two decades, and it somehow manage to rank them. I will do that by looking not only at the statistics, because gaudy numbers do not necessarily lead to positive results.


Stats are helpful, but this article will go beyond the statistics and rank the Yankees top five free-agent signings of the past decade according to value to the team and contributions to overall team success.

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