Javy Vazquez (2004; 2010)
In the middle of the first decade of the twenty-first century, when the Yankees were desperate to reestablish a dynasty, they overpaid Randy Johnson (a disappointment) and Kevin Brown (a disaster). But Vázquez stood out if only because the Yanks failed to learn their lesson. The club acquired Javy before the 2004 season and signed him to a four-year, $45 million contract. "I want to be a Yankee for more than a year," Vázquez said. But one year was all that could be tolerated. The Yanks paid him $9 million before dealing him to the Diamondbacks. Later, in December 2009, Brian Cashman was desperate to extend his rotation and believed that Vázquez still had enough stuff to thrive. The team ignored history and agreed to pick up his $11.5 million salary for one season. Yet again, nothing went right. He struggled to produce a record of 10-10 with a 5.32 ERA. His cumulative stats over two seasons: 24-20 with a 5.09 ERA. For these performances, Cashman had laid out $20.5 million, or nearly $1 million per victory.