How the Yanks landed CC, 13 years ago

Cashman's trip to California helped seal the deal

December 15th, 2021

A version of this story originally ran in December 2017.

It was late afternoon on Dec. 9, 2008, approaching the halfway point of baseball's Winter Meetings in Las Vegas, and Brian Cashman felt his cellphone vibrate. One of 's representatives was calling with an invitation.

By nightfall, Cashman had slipped away and was on a commercial jet bound for Oakland International Airport. He was authorized to offer the free agent left-hander $161 million of the Steinbrenner family fortune. When the general manager awoke some six hours later in a San Francisco hotel room, Sabathia had agreed to become a Yankee.

"We had the opportunity to [meet] in Vegas, but I also wanted to get the opportunity to meet the family if it was possible," Cashman said then. "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."

As he arrived at Sabathia's palatial estate in Vallejo, Calif., Cashman said he was struck by the familiarity of the residence. In a random coincidence, Cashman had been channel-surfing a few months earlier 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.

Then 28 years old, Sabathia was the most coveted free agent in the game, having gone 17-10 with a 2.70 ERA in 35 combined starts for Cleveland and Milwaukee during the 2008 season. He was 11-2 with a 1.65 ERA in 17 starts for the Brewers, firing seven complete games and three shutouts while taking the ball several times on short rest, and he would be rewarded with what was then the richest contract issued to a pitcher.

Talks had been stalled for weeks before Sabathia and the Yankees met twice during those Winter Meetings, with Sabathia in Las Vegas to attend a boxing match between Oscar De La Hoya and Manny Pacquiao. A night after watching Pacquiao's eighth-round TKO at the MGM Grand, Sabathia met with Cashman, then-manager Joe Girardi and special advisor Reggie Jackson in a hotel suite.

That two-hour discussion piqued Sabathia's interest, and the hurler's representatives, Greg Genske and Brian Peters, suggested another Q&A session with Cashman the next day. When that encounter also went positively, the GM suggested that he could follow the left-hander back to California and meet with Sabathia's family. With Sabathia's wife, Amber -- who is now an agent with CAA Sports -- and their three children in the living room, Cashman sold the family on what life could look like in New York.

"When the opportunity was given, that's a flight I had to take," Cashman said.

Bleary-eyed, Cashman walked back into the Las Vegas hotel just after 9 a.m. local time on Dec. 10. The Yankees weren't done shopping. Those Meetings also saw them lay the groundwork to sign right-hander A.J. Burnett to a five-year, $82.5 million contract, with the team introducing Burnett and Sabathia together on the afternoon of Dec. 18 -- 13 years ago Saturday -- at the original Yankee Stadium.

"I think it adds an urgency to get back to where this organization is supposed to be," Sabathia said. "I wouldn't say it's pressure. I would just say that people will play with a sense of urgency in the new stadium, getting back to that. It's definitely exciting."

Those signings, plus the eight-year, $180 million contract extended to first baseman Mark Teixeira in January and a November trade with the White Sox for outfielder Nick Swisher, would help the Yanks claim the 27th World Series championship in franchise history in 2009.

"It was kind of a stressful deal," Sabathia later said of the free-agency process. "I was just trying to make sure I made the right decision. Being here now and coming here and seeing the way people are, I definitely made the right choice."

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