Brian Cashman: Orlando Hernandez Best Yankees Free Agent Signing

Brian Cashman has signed a lot of free agents over the past two decades as the general manager of the New York Yankees. Over that period, he’s brokered some of the richest contracts of any professional sport in the world.

When Bryan Hoch, who covers the team for MLB.com, asked Yankees GM BrianCashman to name the best one, his answer came from a sea of choices. He chose Orlando Hernandez.

A few months after Hernandez defected from Cuba late in 1997, he signed a four-year contract worth $6.6 million. It was a large, risky investment at the time, even for a Cuban superstar, as he was 32 years old and had never thrown a Major League Baseball pitch.

“El Duque” went 12-4 in his rookie season and posted a 3.13 ERA, before performing masterfully in the American League Championship Series and the World Series. The Yankees went to the World Series in each of the initial four seasons of Hernandez’s contract, winning the first three.

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Despite the considerable payoff of the Hernandez signing, Cashman offered Mike Mussina as his 1-B selection. Like Hernandez, Mussina was past his 30th birthday when he signed with the Yankees. Even with Mussina’s MLB track record, history has shown that pledging such large contracts to starting pitchers that age can go horribly wrong. It turned out to be one of Cashman’s best decisions.

“If you want to peel the onion further and say a Major League free agent that we imported, probably Mike Mussina,” he told Hoch. “He stayed healthy, he performed.”

Mussina never had a sub-.300 ERA for the Yankees and he didn’t have a 20-win season until the final one in his career, but perspective and advanced metrics have cast his overall numbers in a positive light.

He pitched his entire career in the AL East. That’s 18 years of small ballparks and PEDs circulating mostly unchecked. For eight years, he had to deal with Manny Ramirez, David Ortiz and all those supercharged battles with the Red Sox. His career was overlapped by Roger Clemens, who also pitched in the AL East and won seven Cy Young awards. Not to be overlooked, Mussina won seven Gold Gloves.

As for Hoch’s picks for the best signings in the history of the Yankees, he chose five, all from the last 40 years.

Catfish Hunter: five years, $3.75 million in 1975

Hunter helped the Yankees win three straight pennants and two World Series titles, including the first with George Steinbrenner as the team’s owner.

Reggie Jackson: five years, $2.96 million in 1976

Jackson’s Yankees tenure may have been rocky at times, but he’s Mr. October and has given his time and insight to the organization throughout the years.

Dave Winfield: 10 years, $23 million in 1980

Winfield’s signing was the richest free agent signing at the time, and he would go on to earn All-Star selections eight times as a Yankee. Overall, he made 12 All-Star games, won seven Gold Gloves, six Silver Sluggers and was a first-ballot Hall of Famer in 2001.

Hideki Matsui: three years, $21 million in 2002

Matsui had a very solid 125 OPS+ in his first three years with the Yankees, earning him an extension through 2009. In his final season with the team, he was named World Series MVP.

Next: Yankees GM Brian Cashman: Why Chris Sale Was “No Sale”

CC Sabathia: seven years, $161 million in 2008

The Yankees won the World Series Sabathia’s first season with the team, and he was a bona fide ace for several seasons after that.

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