This year, however, the Yankees have few major holes to fill on their roster, with the back end of their pitching staff and some spots on their bench representing the most pressing areas of need.
"Your roster is always fluid; whatever you do in the winter, you're going to have to adjust on the run come Spring Training and in-season," Cashman said. "You're constantly looking to be better at every position, though some positions are locked down with full no-trade [clauses] and players that you would have no interest in trading or trying to upgrade -- because you wouldn't be able to.
"There are some obvious spots on the roster where things could develop if they make sense," he added. "We'll keep an eye on it and see where it takes us."
The Yankees made headlines on Tuesday with their winning bid for Japanese left-hander Kei Igawa, who should join Chien-Ming Wang, Mike Mussina, Randy Johnson and Carl Pavano in New York's starting rotation.
Cashman could still bring in another starter this winter, but with young arms such as Darrell Rasner, Jeff Karstens, Philip Hughes and Humberto Sanchez at Triple-A, the club has plenty of in-house options should Pavano or Johnson encounter any health issues before the start of the season.
In fact, on the day before his team learned that it had placed the top bid for the rights to negotiate with Igawa, Cashman made it clear that he didn't feel a strong need to sign a starter.
"I'm open to it, but is it something that we have to do right now?" Cashman said. "I have Wang, Mussina, Johnson, Pavano, and some kids who are hungry and knocking on the door."
The Yankees have also discussed moving Scott Proctor from the bullpen to the rotation, as the right-hander is training as a starting pitcher during the offseason.
"There are a lot of people who believe he could be a successful starter in the big leagues," Cashman said.
Johnson is recovering from back surgery, while Pavano is working with a trainer in Arizona to make sure he's in top shape for Spring Training. Pavano hasn't pitched in a big-league game since June 27, 2005, due to a myriad of injuries.
With Wang, Mussina and Igawa (assuming he signs) penciled in to fill three of the five slots, the Yankees have enough depth to handle a setback for either Johnson or Pavano during camp.
"We could go from within for the fifth spot, which is something that most teams do," Cashman said. "I'll continue to look at the trade and free-agent markets and see what shakes out there, see if it makes more sense to reinforce that way. Time will tell; it's still early in the process."
The only position that isn't set in stone is first base, as Jason Giambi will likely see most of his at-bats as the team's designated hitter. Players such as Shea Hillenbrand and Eduardo Perez have reportedly drawn interest from the Yankees, but Andy Phillips remains a viable option for New York.
"I'd like to find someone we can call an everyday guy there; if we see something off the free-agent or trade market that we feel is fair value, then we'll become aggressive," Cashman said. "If not, then we're more than willing to go with Andy Phillips. We feel is a better player and hitter than he showed last year, so we may turn to him again if we don't find anything that makes more sense."
Phillips started 49 games at first for the Yankees in 2006, but he was never able to find a solid groove. After the Yankees acquired Craig Wilson at the trade deadline, Phillips saw little playing time, getting just 21 at-bats during the final two months of the season.
Aside from first base, the Yankees' biggest needs are a utility infielder, backup catcher and another arm in the bullpen, preferably a left-hander.
The Yankees have a number of solid prospects in their system to use in the trade market, but Cashman is unlikely to deal any of them during the meetings.
"There's no one really untouchable on this roster," Cashman said. "I'm open to listening to anybody, but some guys are more touchable than others."
Mark Feinsand is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.