This time, Cashman not only left the Bellagio hotel, but the entire state of Nevada, escaping to the San Francisco area for an unscheduled meeting. The Yankees hope the extra effort will help them secure their top target in the free-agent left-hander, who met with Cashman for the third time in three days.
Tuesday's meeting with Sabathia, first reported by Newsday, may be a strong sign that the club's odds of fitting its top choice for pinstripes are increasing.
The most recent visit is believed to have been made with attention to the concerns of Sabathia's wife, Amber. The Sabathias have West Coast roots -- he is a product of Vallejo, Calif., approximately 30 miles outside of San Francisco -- and a family of three young children.
"We all know what kind of ballplayer he is," Cashman said on Monday. "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."
Cashman, manager Joe Girardi and special advisor Reggie Jackson met with Sabathia and agent Greg Genske for approximately two hours at the Wynn hotel on Sunday. Jackson took the lead in those discussions, representing a Bay Area product who went on to stardom in New York and looks back upon his Yankees time fondest.
With more items on the hurler's mind as he mulls the Yankees' standing six-year, $140 million offer, Cashman was then invited back on Monday, answering follow-up questions in a meeting of less than one hour with Genske present.
In laying out their plans to upgrade their starting pitching with two or three front-line free-agent options, the Yankees have spoken about "selling New York," a process that goes beyond just the spacious amenities of the new $1.3 billion Yankee Stadium.
In addition, the Yankees would discuss the specifics of what life in the tri-state area would mean for the Sabathias, including but not limited to schools, transportation and entertainment. He will also need to consider the choice between living the Manhattan lifestyle, or in the quieter, leafy suburbs of Connecticut or New Jersey.
"I have no doubt that he can play in New York," Cashman said on Monday. "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."
Girardi remained behind at the Winter Meetings and said he was "very impressed" by his interactions with Sabathia.
"He's been in the American League long enough to know what New York is about," Girardi said. "And CC's personality, I think, would work very well here. He's a guy that wants the ball every fifth day. He's a standup guy, he's a very honest young man. So I think his personality will be great."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.