"I don't feel like we are in a desperate situation here," Cashman said on the YES Network. "I think we have a lot of quality players on this team that won 95 games and fell two games short of a World Series."
While most view the Yankees as the favorite because they can offer the most money for Lee, Cashman said he wasn't sure whether that was true. He said the Yankees have an idea of what they are willing to spend for Lee and their other free-agent targets. Even if another team is willing to pay more, Cashman said the Yankees "are not trying to do anything at all costs."
The likely question for the Yankees and Lee is length. Lee is surely going to command more than $20 million per season, maybe as much as $25 million per year, but will it be for five, six or seven years? His agent, Darek Braunecker, is expected to ask for a contract similar to CC Sabathia's seven-year, $161 million deal. Lee is 32, so the Yankees would prefer to do a shorter term than Sabathia's deal.
"We are going to present offers in our comfort zone, given the age and all aspects of the player's strengths and weaknesses," Cashman said. "We'll see if it works."
To try to get a step on the competition, Cashman flew to Arkansas earlier this week to meet with Lee, his family and his agent.
"Little Rock is an example of us trying to hit the ground running this particular winter," Cashman said.
Cashman said he always tries to get in front of free agents if he can, feeling it creates a comfort level. He said Lee struck him as the same guy he has seen in interviews. He had a very "easy demeanor."
"I had a nice lunch with Cliff Lee and his wife, Kristen, and his agent, Darek Braunecker," Cashman said. "It was just a meet-and-greet. They are going to have more with other teams, too. It is probably just a natural step in the process. Unfortunately, I had a chance to see Cliff Lee do damage against [us] for quite some time, but not get to know him personally, so this was more of a chance to get to know him and exchange information."
At the Joe Torre Safe at Home Dinner on Thursday night, Cashman addressed the incident in which Kristen felt she and other Texas Rangers' family and friends were taunted and spit at during the ALCS.
"It came up," Cashman said. "We talked about it. She loves New York. I don't want to speak for her, but I can just tell you that I don't have any fear of any of the experiences that she's had in the New York area as being an issue here. I can tell you, the feel I got from her and him is that, this is a place that intrigues them a great deal. But unfortunately there's other places that I'm sure will intrigue them as well. But we recognize things can happen in our environment just like any other environment, and I think they recognize that too."
Cashman made it clear how much he wanted Lee, but he said if the Yankees don't get him they will just move on.
"That's when you have to be willing to roll with the punches and have Plan B's, C's, D's and F's up there," Cashman said.
The Yankees will have to compete most notably with the Rangers, but there are wild-card possibilities like the Washington Nationals who could make the Yankees go even further.
"We definitely can play in the big sandbox more than anybody because we are the Yankees," Cashman said. "We certainly aren't successful every time we enter the process. We're trying. I can tell you that."
Andrew Marchand covers the Yankees for ESPNNewYork.com. ESPNNewYork.com's Kieran Darcy contributed to this report.