The progression from the Fall Classic to the offseason was quicker than usual for the Yankees this season, but it is a welcome problem for Cashman and his group, who can now assemble at the Winter Meetings to begin readying the roster for its first title defense in nine years.
While the Yankees have already been in contact with some clubs regarding trade possibilities -- including touching base with the Blue Jays, who have a chip any team would covet in Roy Halladay -- Cashman said he would refrain from contacting agents until the Bombers' budget was set, which was finalized at the end of the week.
As a courtesy to the Yankees' own free agents, among the first numbers to push on Cashman's speed dial will be to Scott Boras, Randy Hendricks and Arn Tellem -- the representatives for Johnny Damon, Andy Pettitte and Hideki Matsui, respectively.
"I don't want to make the mistake of having a conversation with someone else's agent, and it plays out as if I'm pursuing that guy, and someone misinterprets that as I'm not pursuing our [free agents]," Cashman said.
The Yankees were set to gather in Tampa, Fla., on Thursday and Friday of this week to discuss the parameters of their offseason budget, which will be sizable but not as extravagant as it was last winter, when New York shelled out a combined $423.5 million to land CC Sabathia, A.J. Burnett and Mark Teixeira.
Cashman is to arrive in Indianapolis on Sunday with his trusted executives in tow, and the Yankees do have the luxury of seeing some significant dollars freeing from their payroll. Damon and Matsui each made $13 million in 2009, while Pettitte earned $10.5 million with contract incentives.
Other players, like Xavier Nady ($6.55 million) and Chien-Ming Wang ($5 million), earned large salaries despite missing most of the season due to injury. Those subtractions help offer some level of additional flexibility, along with the investments made last winter.
"I'm really pleased about the financial commitments we were allowed to make last winter," Cashman said. "It puts us in a much better place moving forward as we enter this winter signing season."
While the core of the roster is returning for 2010, the Yankees must address left field in deciding if they will meet Damon's desires for a multiyear contract, which could be a two-year deal in the ballpark of the $19 million commitment Bobby Abreu received from the Angels.
Their alternatives are to promote a prospect like Austin Jackson or look outside the organization for help -- a free-agent group that begins with Matt Holliday and Jason Bay.
Despite winning the World Series MVP, Matsui's future in New York appears murky, through no fault of his own. A trusted and respected member of the roster since 2003, Matsui's inability to play the outfield limits the Yankees' flexibility with a percolating plan to have a "revolving-door" designated hitter for '10.
Under that idea, Jorge Posada, Alex Rodriguez, Teixeira and others would log more at-bats as the DH, allowing them time off from their defensive positions. That could be important for A-Rod, who may not need another procedure on his right hip but will still need to protect it at times.
While a Halladay deal would command a healthy sum in talent and dollars, making it far from imminent, the Yankees will somehow have to address their starting pitching -- which manager Joe Girardi described off-hand recently as Sabathia, Burnett "and a bunch of guys."
Pettitte is hammering out his annual tug-of-war between pitching and retirement, and if he is interested, the door should be open.
But the back end is otherwise unsettled, with Joba Chamberlain and Phil Hughes being considered starting pitchers for now -- subject to change -- and a crop of fourth- and fifth-starter candidates that include Alfredo Aceves, Chad Gaudin, Ian Kennedy and Sergio Mitre.
New York's bench will also need retooling, as utility men Jerry Hairston Jr. and Eric Hinske, plus catcher Jose Molina, are all free agents. The Yankees enjoyed their respective veteran presences, but could have ready-made fits from their system in infielder Ramiro Pena and catcher Francisco Cervelli to ease the transition to youth.
"Getting younger just for younger's sake doesn't mean you are going to get better," Cashman said. "You have to pick the right guy to get younger with."
The bullpen is considered to be less of a concern at this point, though certainly tinkering could not be ruled out.
Among other things, Damaso Marte's resurgence gives the Yankees some confidence that the bridge to closer Mariano Rivera could be stronger than they thought, adding his left-handed arm to a mix that could include Phil Coke, Brian Bruney and Dave Robertson.
Whatever choices must be made, Cashman is in no way expecting his shopping list to be complete by the time his plane departs from Indianapolis. But perhaps the Yankees will at least have made a dent in important areas.
"I think we're going to be very careful. Careful doesn't necessarily mean slow," Cashman said. "We're just going to make sure we try to spend it wisely, try to make the right commitments for us -- for the present and the future."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.