By nightfall, the Yankees general manager was airborne, settling into a seat on a commercial jet bound for California. A heart-to-heart meeting and a new contract offer awaited for CC Sabathia, and when Cashman awoke some six hours later, he did so in a changed world -- one where the top free agent on the open market was headed for New York.
"I've been wanting to try and get in front of him for a while now," Cashman said. "We had the opportunity to do it here in Vegas, but I also wanted to get the opportunity to meet the family if it was possible.
"I told them I would be more than willing to fly from Vegas to continue our efforts by meeting in California. They welcomed that idea, so I took advantage of it and bolted."
Upon arriving at Sabathia's palatial estate in Vallejo, Calif., Cashman said he was struck by the familiarity of the residence. In a random coincidence, the GM had been channel-surfing at home in Connecticut and happened across the episode of "MTV Cribs" that featured Sabathia's home.
There was little time to tour the lounge, high-tech theater or cabana, though Cashman had an offer that essentially ensures Sabathia will be able to re-create the experience on the East Coast if he so chooses. The left-hander agreed Wednesday to parameters on a seven-year, $161 million contract with the Yankees.
"It was a beneficial trip and I'm glad I went," Cashman said. "Stay tuned."
Cashman was not at liberty to discuss the pact because it has not been officially completed, but a baseball source confirmed that Sabathia accepted the Yankees' increased offer in the early morning hours, far from the glitzy lights of Las Vegas.
"I think that every time he's engaged me after the first time, it's always been a good sign," Cashman said. "The fact that he wanted to meet with me and would permit me to fly to his home ... I do take that as a real positive sign, no question."
The surprising changes to Cashman's schedule came as the result of a promise to Sabathia and his representatives earlier in the week.
When Sabathia spent the weekend at the Wynn Las Vegas hotel, using part of his travel time to watch Saturday's prize fight between Oscar de la Hoya and Manny Pacquaio, Cashman suggested that he could follow the left-hander back to California for a visit at his Vallejo home if everything progressed well with the Yankees' talks.
A night after watching Pacquaio's eighth-round TKO at the MGM Grand, Sabathia met with Cashman, manager Joe Girardi and special advisor Reggie Jackson on Sunday evening in his hotel suite.
The two-hour meeting opened so many questions for Sabathia that his representatives, Greg Genske and Brian Peters, suggested that Cashman make the mile-long trek back to the Wynn on Tuesday for a Q&A session of less than an hour before Sabathia departed. That encounter also went positively.
Cashman was back at the Yankees' 23rd-floor suite Tuesday when an incoming call from Peters arrived. Sabathia was at home and wanted to invite Cashman to come out to the West Coast as soon as Tuesday, if the Yankees would still be interested in further discussing their offer.
"When the opportunity was given, that's a flight I had to take," Cashman said.
With more financial latitude from co-chairman Hal Steinbrenner in his back pocket, Cashman bought a one-way ticket onto a 5 p.m. PT flight to Oakland and met with Sabathia, his wife, Amber, and their three children, discussing business in the family's living room.
"We made a strong push and I feel a lot of progress was made," he said.
Cashman knew of a flight back to Las Vegas from the Bay Area late Tuesday, but his continued discussions with Sabathia sent him instead to a hotel in San Francisco for the evening, holding a plane reservation for the morning.
"I was anxious to hear from him this morning," Girardi said. "I knew that he was probably going to have a late night. The reports that are preliminary are out there and I got some texts before I talked to Brian this morning. My phone started blowing up pretty early."
Bleary-eyed, Cashman finally walked back into the Bellagio around 9:30 a.m. PT on Wednesday, wearied but ready to continue business as the Yankees' plans move on.
"I think we made significant progress, but there's work to be done," Girardi said.
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.