Yankees: 5 Greatest Free Agent Signings of All Time

The Yankees are usually key players for every major free agent, but which signings have been some of their greatest of all time?

With everything that has transpired over the past seven months, it’s clear this Yankees roster needs some shuffling. Once thought of as a team that buys championships, this era of pinstripe baseball has a new identity, one of homegrown talent. That being said, the pride of rooting for a team built from within will never surpass the feeling of winning a World Series. It’s time to bring in some free agent’s, and not just supplemental pieces. We need some George level stuff here.

Since the birth of free agency in 1976, all Yankee championships have been structured around big free agent pickups: Goose Gossage, Jimmy Key, Johnny Damon and so on. It’s time for the cash man to open his wallet. But in the meantime let’s reminisce and take a look back at the Bombers top five free agent pickups of all-time.

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5. Orlando Hernandez, 4 years/$6.6M, 3/23/1998

Before joining the pinnacle of baseball in 1998, starting pitcher Orlando “El Duque” Hernandez played for the Havana Industriales in the Cuban National Series and was part of two championship teams in 1992 and 1996. He was also a mainstay on the Cuban National Baseball team that took home the Olympic gold at Barcelona in 1992.

As a non-U.S. resident, Hernandez was able to negotiate as a free agent unlike American-born players who must enter through the draft. As a result, he made about 33 times more money than the average rookie in 1998.

Hernandez went 61-40 with a 3.96 ERA and 703 strikeouts over 876.1 innings pitched. But it was El Duque’s postseason dominance that carved out his place in Bomber history. In 15 postseason series he went 9-3 with a 2.55 ERA and 107 strikeouts in 106 innings pitched. He was named the 1999 ALCS MVP going 1-0 with a 1.80 ERA and 13 strikeouts over 15 innings. Dominance.

After three World Series victories in New York, Hernandez brought his knack for the postseason to the windy city. In 2005 he helped lead the White Sox to their first title since 1917, escaping a bases loaded nobody out jam in game three of the ALDS against Boston before ultimately sweeping the Houston Astros in the World Series.

No other Yankee free agent hurler had as much success as “El Duque” Hernandez. He is tied with southpaw Mike Stanton for most World Series titles as a free agent with three and leads in appearances with four (David Cone originally was traded to the Yankees from Toronto before signing as a free agent). Let’s hope that a decade down the road this will no longer be the case.

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