"If I learned anything, I learned that our assessments are accurate about him as a person," Cashman said. "He's a quality guy, whether he picks us or doesn't pick us.
"I think he's going through this process with a genuine sincere effort to make the best decision for himself and his family. We're not being played, we're not being manipulated. We're not being used."
One day after Cashman, manager Joe Girardi and special advisor Reggie Jackson huddled with Sabathia and his representatives a short ride up the Strip, Cashman was summoned back to the Wynn for a few more verbal volleys in a session lasting less than one hour.
This was Cashman's turn to talk. There was a well-planned reason for having Mr. October along for the initial meeting, which was Cashman's first face-to-face interaction with Sabathia, even after his years of service in the American League for the Indians.
"I brought Reggie in because Reggie is from the Bay Area and went through the same process as a free agent at the relatively same age," Cashman said. "He's someone who came to New York, conquered New York, left New York, and can even give the perspective of how he feels after the dust settled."
Sabathia's preferences for the West Coast and the National League have been well documented, but the Yankees believe they are firmly in the running to acquire his services.
Their thought, however, is that they may not be at the front of the line.
"We are definitely on his list. There is a list," Cashman said. "We just happen to be a member of that list. It's nice to have choices, I guess."
There is a sense that Sabathia may be sitting on the Yankees' six-year, $140 million offer as a safe haven, unwilling to sign until the rest of the marketplace develops. Cashman rejected the idea that Sabathia may be steering away from the Yankees based solely upon New York's bright lights and aggressive media market.
"I have no doubt that he can play in New York," Cashman said. "I just think that he's lining up his choices and just trying to pick the best one. I don't believe he has any fear factor of New York, or anything of that nature."
The Brewers are the only other club with a known offer, reported at five years and $100 million. GM Doug Melvin met with Sabathia's representatives on Monday and tentatively set plans for another meeting Thursday, though other clubs remain on the fringes.
Sabathia told Dodgers GM Ned Colletti that he wants to play in Los Angeles in a chance meeting on Sunday, and the Giants have discussed parameters of a potential deal with Sabathia's agent, Greg Genske, though no formal offer has been presented.
In the meantime, the Yankees can do little but wait and see what Sabathia's final decision will be.
"We all know what kind of ballplayer he is," Cashman said. "He's a tremendous family man and he's got a wife and three kids. He's got a life choice to make that will direct where they'll reside. He's going through the process, and he's going to dot every I and cross every T."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.