NEW YORK — Back in 1998, little more than a month after being named the general manager of the Yankees, Brian Cashman encountered a moment of truth. Orlando “El Duque” Hernández was close to signing out of Cuba. But Cashman waffled, still haunted by a failure from the summer before, when the Yankees moved mountains to acquire Hideki Irabu only to watch him flop. It took some nudging from the veteran scout and executive Gordon Blakeley for Cashman to stop balking and move forward with El Duque.



“You’ve got to swing for the fences or you might miss out on the next Cy Young Award winner,” Cashman said, recalling Blakeley’s advice at the time.



That was 20 years ago, and though Hernández didn’t win a Cy Young Award, he pitched in four World Series and helped the Yankees win three of them. Years later, Cashman would call the risky $6.6 million signing the shrewdest of his tenure. That example came up on Saturday...