The Yankees won 97 games and brought home an American League East title, but that didn't seem to erase much of the sting as the club went home early, dispatched by the Tigers in the first round of the postseason.
Their offseason has been a relatively quiet one, by Yankees standards, although it has been efficient.
With his own contract situation quietly hammered out, Cashman left no question that the club's top priority was to ensure CC Sabathia was in place as its left-handed ace not only for 2012, but years beyond that.
"He was certainly the most important piece as we entered this process," Cashman said.
That was all taken care of by Halloween, as Sabathia and the Yankees agreed to a new deal that will have the 31-year-old Sabathia earning $122 million through 2016.
Many generally assumed that Sabathia would make use of the opt-out clause in his contract, and a proactive offer helped avoid a sticky situation like the one Alex Rodriguez and the Yankees went through after the 2007 season.
"I didn't want to be a part of that being a free agent and doing everything, opting out and all that stuff," Sabathia said. "It was clear to everybody that I wanted to be a Yankee, wanted to end my career as a Yankee. Hopefully, I've done that."
In fact, considering the course the Yankees' offseason took last year with Derek Jeter's contract situation, this already figures to be a less turbulent winter in the Bronx.
Cashman still identifies his top priority as "pitching, pitching, pitching," and the Yankees added some cushion for their rotation over the Thanksgiving weekend by bringing back veteran Freddy Garcia on a one-year deal.
The 35-year-old right-hander will earn between $4 million and $5 million this year, picking up a raise after he went 12-8 with a 3.62 ERA in 25 starts and one relief appearance for New York, coming to camp on a Minor League contract.
That gives the Yankees five starting pitchers, with A.J. Burnett, Phil Hughes and Ivan Nova all set to return, plus possible spring contention from hopefuls like Hector Noesi, Dellin Betances and Manny Banuelos.
There may be other names coming. The Yankees have had varying levels of interest in free-agent options like C.J. Wilson, Mark Buehrle, Edwin Jackson and Yu Darvish, and Cashman could use the Winter Meetings to feel out those situations, as well as talk about potential swaps with other clubs.
But while other teams will flirt with pursuits of stars like Albert Pujols, Jose Reyes and Prince Fielder, Cashman says that the Yankees aren't expecting to deal for any big hitters.
"As we enter the process this winter, I don't anticipate a bat being of need at all," Cashman said. "I anticipate people knocking on our door about the current bats we have. Offense is not a problem with this club."
There have been rumors of the Braves having interest in infielder Eduardo Nunez, and Jesus Montero has repeatedly been a popular trade target for other teams. But both players impressed in 2011 and could be viewed as cogs for the Yankees' future.
The Yankees are also high on catcher Austin Romine after his first taste of big league duty, and his progress could wind up displacing Francisco Cervelli from his backup catching role, making him a possible trade chip.
In other needs, the Yankees would like to shore up their bench, holding some interest in retaining infielder Eric Chavez and outfielder Andruw Jones.
Over the last few years, the Winter Meetings have presented busy times for the Yankees. In 2008, Cashman escaped Las Vegas and jetted off to California to personally deliver a seven-year, $161 million contract offer to Sabathia, a tactic that worked.
In 2009, Cashman not only was able to help coordinate a three-team trade with Detroit and Arizona that delivered Curtis Granderson to New York, but he also secured the services of Andy Pettitte for his farewell season.
Last time around in Tampa, Fla., the Yankees did get Jeter's signature on a new contract, but they whiffed on top target Cliff Lee. Who can tell what Dallas will bring?
"We will be challenged with, I'm sure, people knocking on our door with various interest levels in assets," Cashman said.
This much seems certain: Cashman and his staff figure to have their hands full with hot rumors, wild proposals and perhaps the occasional room-service delivery.
"I'm just going to try to improve on what we have, which is very very good, as is," Cashman said. "Is there a way to make it better? I think so, and we're certainly going to pursue it to the fullest extent."