Ten months later, the Yankees have arrived at the doorstep of World Series glory, riding Cashman's California prize, CC Sabathia, and a host of other individual parts to baseball's ultimate stage. As they always do, some will criticize Cashman and the Yankees for doing so with a payroll roughly 43 percent greater than that of their closest competitors. Most around New York will laud Cashman for making the right moves with that money.
"We have deeper pitching right now," Cashman said recently of the 2009 club's ability to succeed where previous versions could not. "We're deeper on the bench, the bullpen, offensively and we're healthy," Cashman said. "The teams we had with Joe Torre were well prepared and quality, but this particular team is a stronger team."
It has also led Cashman to his current spot, a more secure perch within the team's hierarchy than perhaps ever before. When the Padres dismissed Kevin Towers earlier this month, Cashman became Major League Baseball's third-longest-tenured general manager. Since 1998, he has stood at the helm of baseball operations, though he enjoys more power and autonomy now than he did then.
Consider two winters ago, when many within the organization were pressing for the Yankees to acquire Johan Santana, who was available on the trade market. Cashman dangled an offer of Phil Hughes and Melky Cabrera in front of the Twins, and when they balked, so did he. Knowing that Sabathia, A.J. Burnett and Derek Lowe were all due to be free agents after the 2009 season, Cashman stood firm.
Longest-tenured MLB GMs
|Kenny Williams||White Sox||10/24/00|
It was a calculated risk. The Yankees missed the playoffs that year for the first time in Cashman's tenure. But they also held onto Hughes, a critical bullpen piece this season, and Cabrera, who has developed into their starting center fielder. And then they went out and wreaked havoc on last winter's free-agent market, shelling out $423.5 million for Sabathia, Burnett and first baseman Mark Teixeira.
Cashman also swapped little-used reserve Wilson Betemit for Nick Swisher, an outfielder coming off a dreadful season in Chicago, and re-signed Andy Pettitte to a one-year, incentive-laden deal.
Swisher hit 29 home runs as the starting right fielder. Pettitte cashed in on the incentives. And the Yankees likewise cashed in on the success.
"I think this team is one of our better teams we've had in a while," Cashman said after the Yankees downed the Twins in the first round of the playoffs.
It helps, of course, that the Yankees were able to offer more money to Sabathia and Teixeira than any team in baseball, that they were able to write a blank check for Alex Rodriguez after he opted out of his contract two autumns ago, and that they are able to bask in the revenue of a sparkling new stadium and the largest media market in the country.
But those are not the only reasons for Cashman's success.
In addition to making the right free-agent moves this winter where in the past his team has faltered, Cashman has deftly maneuvered within an organization that at times has shook under the irascible George Steinbrenner, and at times has split down the middle due to Steinbrenner's trusted faction in Tampa, Fla.
Cashman has survived where others have not. Since Steinbrenner took over the team in 1973, no GM spent more than five years on the job -- and only Gene Michael, who was there from 1991-95, lasted that long. Winning breeds contentment, and the Yankees were winning.
Now, after surviving a dry spell, Cashman and the Yankees are winning again. Acquiring Sabathia is a significant reason why; avoiding the pitfalls of his profession is another. And thanks in large part to Cashman, and perhaps more than ever since their dynasty years of the late 1990s, the Yankees are acting and winning like a team.
"They've just been a family," said Hal Steinbrenner, George's son. "They have been a team every single day, every single game. And they play like that, and that's why they're here."
Anthony DiComo is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.