Here’s how the Yankees landed CC

May 31st, 2019

This excerpt of Mission 27: A New Boss, a New Ballpark, and One Last Ring for the Yankees’ Core Four, by Mark Feinsand and Bryan Hoch, is presented with permission from Triumph Books. For more information or to order a copy, please visit

The final turnstile had spun as Brian Cashman walked to his office in the soon-to-be-vacated Yankee Stadium, and an autumn chill whipped through the thousands of faded blue seats in the grandstand. He’d often said that the Yankees were out of his hands when the postseason arrived; there were no trades or roster moves to make, leaving him to nervously munch popcorn or prank employees while the next nine innings played out.

As Cashman rode the elevator, pulled open a glass door, and passed the two World Series trophies that rested at the entrance of the executive offices, he experienced an even more uncomfortable sensation. The Yankees hadn’t been playoff observers for a non-strike season since 1993, and Cashman despised turning on the television to check scores. October baseball belonged in the Bronx, and to make that happen again, he had work to do.

Joe Torre's exit after 2007 had set the Yankees upon the course Cashman desired; Torre remained fiercely loyal to those who had helped to place World Series rings on his sizable hands, but that group was now a minority. The attitude leaked into the clubhouse, where Derek Jeter would privately grouse about his new teammates: "Those guys don't know how to win championships.”

“Culture was an issue in that clubhouse,” Cashman said. “We were broken, and it needed to be addressed.”

For a quick fix, they’d need to spend big. Paced by starting pitchers CC Sabathia and A.J. Burnett, the free-agent class was top-heavy, while the position player front was headlined by sluggers Mark Teixeira and Manny Ramirez. 

Sabathia had showcased his physical and mental fortitude during his three-plus months with the Milwaukee Brewers, going 11–2 with a 1.65 ERA in 17 starts. To the chagrin of his agents, the hulking 6’6”, 300-pound lefthander took the ball on short rest in each of his final three starts, helping Milwaukee chase a postseason berth. It was a stunning sign of sacrifice for a pitcher who was said to be targeting a contract of $150 million or more that winter.

"CC was a massive target,” Cashman said. “And not just for what he could do on the field.”

Cashman envisioned Sabathia as someone who could add a fresh outlook to the clubhouse, succeeding where Jason Giambi or Alex Rodriguez had failed to wrest control away from staples like Jeter and Jorge Posada. The Yankees had competition, as Sabathia’s high-octane fastball and teddy bear personality had the baseball world lining up to wave dollar bills in his direction.

The Brewers hoped to retain their new ace, though they were only able to offer five years and $100 million. He enjoyed his time with Milwaukee, but hadn't been there long enough to entertain a hometown discount. The Red Sox were also said to be interested in Sabathia, but the biggest threats would come from the West Coast. The Dodgers, Angels and Giants were all expected to chase Sabathia, who grew up in the North Bay city of Vallejo, California, 30 miles north of San Francisco and 25 miles from Oakland.

The annual Winter Meetings, which assemble the baseball world for four days of rumors, whispers, and signings, took place that year at the Bellagio Hotel and Casino during the second week of December. Cashman prepared to pitch Sabathia in Las Vegas, joining the millions of annual visitors who dream of leaving Sin City with newfound fortune.

Exiting a suite that overlooked the Bellagio’s iconic fountains, Cashman made the one-and-a-half-mile trek north on Las Vegas Boulevard to the Wynn Hotel, where he scheduled a meeting with Sabathia and agent Brian Peters. Manager Joe Girardi and Hall of Famer Reggie Jackson — a Bay Area native, like Sabathia — tagged along as reinforcements.

The Yankees went high-tech in their efforts. Cashman produced a DVD that the team had commissioned, offering Sabathia a virtual tour of the stadium site. It featured video messages from construction workers and team employees, imploring the pitcher to be a part of a new era in Yankees history.

"There were construction workers saying, 'Come, CC,'" Sabathia said of the video, which Cashman still keeps stashed in an office cabinet. "It was a bunch of different people around the stadium, people I still see when I'm walking into the stadium right now. It was dope. That was a huge thing for me: them getting out of the old stadium and me being able to play in the new stadium. I was really excited about that."

As Cashman and Girardi listened, Jackson dominated the meeting. "Mr. October” doled out signed baseballs and regaled Sabathia with stories of his glory years, offering what he believed was his best sales pitch to woo Sabathia. The hurler viewed Jackson as a living legend, but at this moment, Sabathia was more concerned with his own future than Jackson's past.

"I was a huge Reggie fan growing up, and my family had been, too, with him playing in the Bay Area for that long," Sabathia said. "It was cool having him be there, but we really couldn't get anything done."

Peters called Cashman the following day and requested a second meeting at the Wynn, which the general manager recalled as "a good, strong talk." Jackson did not attend, freeing Cashman to lay out a more complete proposal to Sabathia, during which he stressed the need for a strong, team-first personality to mend a clubhouse in need of a makeover.

"CC was interested and open to coming here, but there were also concerns because he knew we had a broken clubhouse,” Cashman said. "He said that was [the perception] around the whole league. So I talked to him about, 'That's one of the reasons we're talking to you — not just because of who you are as a player, but someone who brings people together.'"

During his 7 1/2 seasons with the Cleveland Indians, Sabathia would routinely invite teammates to Cavaliers games, and cookouts at the hurler's home were commonplace. Those types of gatherings were not part of the Yankees' culture, and Cashman loved everything he heard.

That Sabathia had averaged more than 14 wins and 207 innings over his first eight years didn’t hurt, either.

The Yankees had made an intriguing pitch, but Sabathia remained uncertain. He and his wife, Amber, had just welcomed their third child, Cyia, in October 2008. Aware that they would not return to Cleveland, the couple had spent the first part of the offseason clearing out their home and shipping boxes to California.

"I remember sitting in the offseason and talking to Amber, and we're like, 'Wherever we sign is where we're going to live,'" Sabathia said. "We were tired of moving around. We wanted to be set somewhere. We just started looking at possible places we wanted to play. It was the Dodgers, Anaheim, and then New York."

Sabathia's extended family still lived in Northern California, so landing in Los Angeles or Anaheim would place their loved ones a short flight away. Any of those teams could make him richer than he had ever imagined. So what would be the deciding factor?

"I felt like I was comfortable on the money," Sabathia said. "But I wanted to win more than anything, so once I kind of figured my No. 1 thing was wanting to win, there was no other place to choose."

Sabathia had more questions for the Yankees. Peters reached out to Cashman again, requesting a third meeting. This time, it wouldn't be in Las Vegas. Sabathia had returned to his home in a gated community near Fairfield, California, where he wanted to sit down one more time with the GM. Peters provided the address, and Cashman booked a one-way ticket to Oakland.

"I'm like, 'I'll do whatever you need,'" Cashman said. "I snuck out of there and I remember saying, 'I've got to be John Calipari. I've got to get in that house and I've got to get the commitment from the recruit.' All I could think of was John Calipari at the University of Kentucky and I was like, 'I've got to close this recruit out.'"

A car service shuttled Cashman to Sabathia's front door, and the GM produced a selection of Yankees swag for Sabathia’s kids. Cashman told Sabathia that he’d seen the house before, on an episode of MTV Cribs. Seated in a luxurious double-height living room, Sabathia said that he was giving serious thought to life in New York but expressed apprehension about a future with the Yankees.

According to friends, chief among Sabathia's concerns was the prospect of throwing to Posada, whose defensive reputation around the league was not particularly strong. Cashman assuaged those fears, listing a number of All- Stars and future Hall of Famers who had thrived with Posada calling pitches.

A Connecticut resident at the time, Cashman answered all of Amber's questions about raising a family in the New York area, describing lush, family friendly suburbs that were close enough for the couple to enjoy Manhattan’s nightlife. When Amber mentioned that she loved the Macy's Thanksgiving Day parade, Cashman promised that the Yankees could get her front-row seats.

"I wasn't really sold about coming to New York after the very first meeting," Sabathia said. "When Cash came to California, we talked, and he gave me and Amber the chance to ask him questions, selling us on the family side of it and having a place to live. I was just thinking in New York, you live in the city, and my kids would be growing up with no grass lawn and stuff. Once we talked about places to live outside the city and I would be comfortable, I felt good."

As Sabathia acknowledged that he could see himself in pinstripes, Cashman and the hurler swapped dollar figures. Cashman had boosted an initial six-year, $140 million proposal by a year, offering seven years and $161 million, surprising Sabathia by including an opt-out clause after the third year.

It was an aspect of the deal that Sabathia said he hadn't even thought about, but Cashman’s willingness to add an escape hatch sent a message: we’re so confident that you’re going to love New York, we’ll let you leave if you don’t.

“I went in there and hit him over the head with a lot of money,” Cashman said. “They told me they were worried about making such a commitment and being stuck here. So I remember on the plane, I thought about the opt-out.”

Cashman spent the night in a San Francisco hotel, catching a quick snooze before boarding an early-morning flight back to Vegas. A few hours after exiting Sabathia’s home, Cashman received the call he was pinning his hopes upon. Sabathia was in.

"With him selling us on a good place to live, the opt-out after three years if I didn’t like it, and having a chance to win every year—once they walked out of the house, I was like, 'I'm sold. I'm done,'" Sabathia said. "I was set on being a Yankee. I was excited."