"There are a lot of areas to focus on this winter -- more than previous winters," Cashman said.
Cashman must rebuild a rotation that has just Sabathia and Ivan Nova as its locks at this moment. The GM also must answer questions at three infield spots, trying to retain free agent Robinson Cano, awaiting the outcome of A-Rod's suspension appeal and hoping for Derek Jeter's successful return from an injury-marred campaign.
There are also questions in the bullpen, the outfield, catcher and the bench. The Yankees have several arbitration-eligible players that they intend to retain, which will help fill some of the holes, and plan to show interest in their own free agents -- particularly Cano, who is set to test the open market.
Having already checked off one of their first priorities in retaining manager Joe Girardi, who signed a four-year contract extension this month, the Yankees are well aware that the finished product may look quite different than the roster that completed the season on Sept. 29 in Houston.
"I always think the Yankees are going to do whatever they feel is best to get better as a club," Girardi said. "Our job is to get the best players we can. We're going to probably have to use our Minor Leagues as well. We need these kids to develop, to get better and play a role.
"If you look at the run the Yankees have had over the past 16 to 17 years, the farm system played a very important role. We need that to happen again, because you can't just go out and buy every free agent at every position. You won't be able to build a team and you won't have enough money. I think that through the Minor League system, the free agents and players that we have, we'll be very good."
Speaking in interviews after the season, Yankees managing general partner Hal Steinbrenner expressed disappointment in the club's player-development system, noting that the Minor League chain was largely unable to help when a rash of injuries devastated the big league roster.
Steinbrenner has also spoken often of his objective to reduce payroll below $189 million for the 2014 season in order to take advantage of luxury tax incentives. Steinbrenner has been quick to remind questioners that it is a goal, not a mandate, and will not come at the expense of fielding a championship-caliber team.
"I have faith in our organization," Girardi said. "They're going to give us whatever we need and whatever they can to make this the best team that we can be, and to be a championship-caliber club. I know there's a lot of things to answer to this year, question marks that we have, but I have faith."
Free agents: 2B Cano, RHP Joba Chamberlain, OF Curtis Granderson, DH Travis Hafner, LHP David Huff, RHP Phil Hughes, RHP Hiroki Kuroda, LHP Boone Logan, 1B Lyle Overbay, LHP Andy Pettitte (retired), IF Mark Reynolds, RHP Mariano Rivera (retired), SS Brendan Ryan, IF Kevin Youkilis, LHP Mike Zagurski.
Arbitration-eligible: C Francisco Cervelli, CF Brett Gardner, RHP Shawn Kelley, IF Jayson Nix, RHP Nova, RHP David Robertson, C Chris Stewart.
Contract options: SS Jeter ($9.5 million player option).
Non-tender possibilities: Nix, Stewart.
Areas of need
Starting rotation: Sabathia and Nova are the only locks to return, so the Yankees are expected to be serious bidders for Japanese right-hander Masahiro Tanaka. They would like to retain Kuroda on a one-year deal, and hope that Michael Pineda will be healthy enough to contribute. David Phelps and Adam Warren could compete for rotation jobs next spring.
Bullpen: From "Enter Sandman" to "Sweet Home Alabama?" David Robertson is likely to take over the closer role, though it is possible the Yankees could check in on a free agent like Joe Nathan. Logan could be back as a left-handed reliever; he appeared headed for a multi-year deal in free agency, but needed elbow surgery after the season.
Catcher: Brian McCann is expected to draw the Yankees' interest, as they lacked power production behind the plate after letting Russell Martin depart as a free agent. Stewart is a non-tender candidate and the Yankees have Cervelli, Austin Romine and J.R. Murphy as their in-house catching choices.
Second base: Cano is the top free agent on this year's market, so he isn't likely to find his landing spot quickly. Cano linked with Jay-Z's new Roc Nation Sports venture and has reportedly asked for a 10-year, $305 million deal; the Yankees want to keep him, but will not go to that neighborhood after watching A-Rod's massive deal play out. It's not clear if any other team would bid that high.
Shortstop: Jeter is being penciled in as the starter, but he missed most of the year to injury and turns 40 in June, so it would be prudent for the Yankees to seek depth. Stephen Drew of the Red Sox or Jhonny Peralta of the Tigers could be fits; light-hitting, slick-fielding Ryan also did a nice job after being acquired in September. Eduardo Nunez or Nix would be the in-house choices.
Third base: Cashman said the Yankees are proceeding as though they'll have A-Rod and his $25 million salary on the active roster. A final decision on Rodriguez's suspension could be announced in December, so the Yankees may only know then if they need to chase another third baseman. A fit like Mark Reynolds might be useful, since he could also play first base if Teixeira needs help.
Outfield: The Yankees have Soriano, Gardner, Suzuki and Vernon Wells set for the roster, but that still seems subject to change. It's likely they'll make a qualifying offer to Granderson; he'd be a good value at $14.1 million to play right field, and would like to return. There has also been talk of mutual interest with Carlos Beltran, but the Yankees seem to have more pressing needs.
Bench/DH: Typically, the Yankees wait until January to fill out these spots with veterans, and they've found success with players like Eric Chavez and Raul Ibanez in the recent past. The DH role may be more complicated this year since Jeter figures to need time there; Wells gives them another in-house option, and the Yankees aren't likely to retain Hafner, Overbay or Youkilis.
2014 Payroll: The reasons behind the $189 million objective have been well-examined by this point, but the figure is reachable. The Yankees currently have about $89 million committed to their six players under contract for next season, and estimates are that they will spend approximately $15 to $18 million more on arbitration-eligible players. After Jeter triggers his player option, the Yankees could have about $75 million to fill out the roster while still getting under the $189 million mark.