Just 12 months later, Cashman has been lauded for the series of moves that have shaped this year's club, most notably the free-agent signings of CC Sabathia, Mark Teixeira and A.J. Burnett.
"Every winter when you make those acquisitions -- whether it's trades or free agents or whatever you do for your club, or promote from within -- it's with the hope and expectation to be the last team standing," Cashman said in an exclusive interview with MLB.com. "So the fact that we're in a position to be playing for a world title, yes, that's what you envision. That's what you hope, especially when you put that kind of money on the table."
It was Cashman's decision two winters ago to squelch trade talks for Johan Santana, a decision which allowed him to free up enough resources last December to pursue three of the top free agents available. At the time, after Santana went to the Mets and Cashman's Yankees missed the playoffs, many criticized his inaction.
Now, Cashman feels vindicated.
"I wouldn't say 'Told you so,' but I think that we were in the middle of a process that wasn't complete," Cashman said. "A little panic sets in when things aren't as smooth as everyone might like when you're going through that process of rebuilding and getting back on line. That comes with the territory. It doesn't make it easier to go through it."
With the Yankees now in the World Series against the Phillies, Cashman said, fans feel more comfortable with the direction of the team.
"I think people have a healthier viewpoint of this franchise, whether I'm here or not, that it's actually in good hands, and the ownership is stable, and this beautiful ballpark is going to provide so much for our fans, and that the future holds bright coming through that farm system," Cashman said. "I think the viewpoint's a lot better now than it was then."
"Like anything else, last year Joe went through a learning process with the press," Cashman said. "That's all been worked through. Like anything else, you assess a problem and you find a solution that works."
Cashman, now, appears more secure than at any point during his tenure with the Yankees. He is the third-longest-tenured general manager in baseball, and though critics point to his inability to win with what's consistently been the largest payroll in baseball, advocates point to how Cashman has been able to spend it.
Count George Steinbrenner among his fans. The Yankees owner, who was at Game 1 here, has stood by Cashman throughout the decade, even when things were not going as the Yankees envisioned.
The affection, naturally, is mutual.
"Obviously he's excited to be here," Cashman said. "This is his pride and joy -- this franchise, this ballpark. He's very proud of this team. He wants us to get after it and bring one home for the city of New York. It's as simple as that."
Anthony DiComo is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.