Jeter will have a job soon, and it's likely to be with the same team he has always worked for. The question is for how long and for how much money. Cashman went to work on resolving that recently, when he -- along with Yankees managing general partner Hal Steinbrenner and president Randy Levine -- met with Jeter and his agent, Casey Close, in Tampa, Fla., where the Yankees' Spring Training headquarters is located and the All-Star shortstop makes his offseason home.
Cashman and Jeter, making an appearance at Joe Torre's Safe At Home Foundation benefit, didn't get into the specifics of the meeting or whether contractual figures were exchanged. But Jeter said he was not asked about switching positions.
"It went well," Jeter said, adding that he didn't come out of it feeling any better or worse.
"I'm sure there's probably speculation of what went down, but really it's not that big a deal," the 36-year-old said, "because it's not like I'm meeting them for the first time. It wasn't that complicated."
Jeter is coming off the final year of a 10-year, $189 million contract. Though there is little doubt he'll return to the Bronx to finish out a potential Hall of Fame career, some expect the signing process to take a while because of the possible value and length of his new contract, as well as the delicate situation of dealing with an icon like Jeter.
Jeter, who made $21 million in 2010, is said to be seeking a four-year deal, while previous reports have stated the Yankees wouldn't be willing to commit more than three years.
Cashman is hoping to make this as smooth a process as possible.
"I don't think there's any expectation from our perspective that this is going to get messy," the Yanks' GM said. "It's business. Two sides have a chance to sit down and discuss what's important to them and where they're trying to go and why, and the reasons behind it. You talk through every aspect, both good and bad, and you find common ground. That's what I'll do with every negotiation. Just some play louder in the public eye, obviously."
Jeter set career lows with a .270 batting average and .340 on-base percentage in 2010, and his range at shortstop has been questioned -- despite winning his second straight and fifth career Gold Glove in 2010.
But then there's the undeniable aspect of his stamp on the organization, the franchise and all-time records he has set, his intangibles, and the likelihood that he still has productive years left in him.
With that, the two sides are expected to go back and forth about money and length of contact. But they can perhaps find one common ground.
"I think that we both want the future to be in pinstripes," Cashman said. "Absolutely, there's no doubt about that. I'm confident that he wants us as much as we want him."
Yankees first baseman Mark Teixeira was accepting a Lou Gehrig Sports Award from the ALS Association's annual dinner at the nearby Marriott Marquis, and he told reporters beforehand that he is "100 percent" sure the Yankees' Core Four of Jeter, Andy Pettitte, Jorge Posada and Mariano Rivera will stay intact.
"That's the easiest question you'll ever ask," Teixeira said. "Those guys are Yankee legends. They're gonna be Yankees forever. It doesn't matter -- get the contracts done. The Yankees want what's best for those guys, and those guys want what's best for the Yankees. So they're going to come to an agreement."
When asked about Hal Steinbrenner indicating that Jeter negotiations could get "messy," Teixeira said: "I don't know what 'messy' means -- whether that's how long it's supposed to take, who knows. You do have to appreciate that Hal is running a business and you have to negotiate. Derek and Hal are going to negotiate and in the end they're going to come to an agreement."