50 Most Notable Yankees Free Agent Signings: CC Sabathia

By the mid-to-late-2000s, it was readily apparent the dynasty years were over. The Yankees hadn’t reached a World Series since 2003. Perhaps worse, they’d allowed the Red Sox to break The Curse, with one of sport’s wildest combacks in the ALCS That Shall Not Be Talked About. Despite those setbacks, however, the Yankees continued to keep winning, at least in the regular season.

Until 2008. That season, the unfathomable happened. The Bronx Bombers won a paltry 89 games, and unlike their 87-win 2000, that was was only good for third in the American League East behind Boston and Tampa Bay. And it wasn’t close. New York lagged eight games behind the Rays for the division and six behind Boston for the wild card. It was the first time the club missed the playoffs since 1993, as the lights were turned out at the old Yankee Stadium not in playoff glory but September irrelevance.

Clearly, changes needed made. And so we got the 2008 offseason, which saw the Yankees sign a flame-throwing right-hander coming off an 18-win season for the Blue Jays, a Hall of Very Good first baseman, and, most importantly, the unquestioned ace and crown jewel of the 2008 free agent crop: Carsten Charles Sabathia.

CC Sabathia
Signing Date: December 10, 2008
Contract: 7 years, $161 million

Much of CC’s story is well-known to PSA readers who followed his playing career and who read Andrés Chávez’s write-up of the Sabathia signing as part of PSA’s 25 Smartest Moves of the Past 25 Years series in 2022. But let’s play the hits of his pre-Yankees days anyway.

Selected by Cleveland as a southpaw out of Vallejo High School in California, Sabathia was the 20th overall pick of the 1998 MLB Draft. Debuting just three years later at age 20, CC promptly carved through the American League, winning 17 games and allowing the fewest hits per nine inning of any qualified pitcher in the league. For his efforts, he was rewarded with a second-place finish in AL Rookie of the Year voting, behind Japanese phenom, future Yankee teammate, and fellow Hall of Famer Ichiro Suzuki.

Fast-forward several years to 2008, with Sabathia set to enter free agency after the season, fresh off winning the 2007 AL Cy Young Award. In early July, the Milwaukee Brewers, determined to go do what they could to snap their 26-year playoff drought, set their eyes on the towering southpaw. In short order, they got him. Once in Milwaukee, Sabathia put together one of the great stretch runs in recent memory.

CC made 10 starts for the Brewers through late August. Five of them were complete games. In late September, he went to another level. His final three starts were all on three days’ rest, making his agency sweat by sticking his left arm out for the Brew Crew. The last of those outings, in Game 162, was another complete game, to get Milwaukee to October. CC spent the entire second half of the season aura farming, long before we’d ever heard the term.

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Once the season ended, Sabathia entered free agency, fresh off his torrid second-half performance for Milwaukee. As free agency progressed, it did not look overly likely Sabathia would don pinstripes as talks between the two sides stalled.

Fast-forward again, this time to the Winter Meetings. A pair of meetings early on laid the groundwork for what ended up being the decisive moment. On Tuesday, December 9th, general manager Brian Cashman’s phone buzzed. On the other end, Sabathia’s camp was inviting him to California. In short order, Cashman was on a plane and headed to Oakland, with ownership’s approval to spend big bucks on the big lefty.

On Wednesday, December 10th, Sabathia and Yankees finalized what was the largest free agenct contract ever given to a pitcher at the time: 7 years and $161 million. To get the deal done, Cashman had to overcome serious qualms on Sabathia’s part.

First, CC was eyeing the Dodgers or Angels in free agency, which made sense considering his California home. Second, and perhaps more worrying, he was concered about the Yankees’ culture, specifically the clubhouse and the Derek Jeter-Alex Rodriguez divide. “We had a reputation for not being together. We had a reputation of fighting each other, and that was a big concern there,” Cashman recounted after the 2009 World Series.

Cashman leaned into Sabathia’s worry. Cashman admitted the clubhouse was broken and that a major reason the club wanted to invest in Sabathia was for his leadership skills, in the hope he could heal the Yankees. CC’s wife Amber helped pitch the Yankees to him, and Sabathia quickly decided to embrace the challenge. “I had been a big part of why the Cleveland clubhouse was fun, and why we won, even if I didn’t want to take credit,” Sabathia recalled in his autobiography. “I was ready for the free-agency uncertainty to be over. Right there, I decided to sign with the Yankees.”

A week later, the Yankees introduced Sabathia, alongside fellow newcomer A.J. Burnett.

The return on investment was almost immediate. Although Sabathia got shelled on Opening Day, he quickly recovered and when the regular season ended, he’d paced the Junior Circuit with 19 wins as the Yanks won 103 contests and stormed back into October.

CC took the ball for Game 1 of the ALDS against Minnesota. Over 6.2 innings, he allowed two runs, one earned, as the Yanks won 7-2 en route to sweeping the Twins. The 2000s playoff nemesis Angels loomed in the ALCS. Running a three-man rotation of Sabathia, Burnett, and the venerable Andy Pettitte, the Yanks gave CC the ball for Games 1 and 4. New opponent, same results. Two more wins for Sabathia earned him ALCS MVP honors, and the Yanks vanquished the Halos in six to return to the World Series for the first time since losing to the Marlins in 2003.

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Facing the Philadelphia Phillies, the Yanks again handed the ball to CC for the series opener. As usual, he held up his end of the bargain. Seven innings of two-run ball will generally get the job done. Just not on a night when Cliff Lee threw a one-run complete game. CC’s former teammate absolutely dominated and the Phils were out to a 1-0 series lead.

Three days later, with the Yankees leading the series 2-1 after taking Games 2 and 3, Sabathia took the ball and again held down his playoff opponent. This time, 6.2 innings of three-run ball was enough to leave with the lead. The Phils battled back to knot the score at 4-4, but A-Rod delivered one of the biggest hits of his career in the top of the ninth to score two and New York held on, leaving them one win short of baseball immortality. After losing Game 5, New York clinched their 27th and most recent championship with a Game 6 victory.

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Game 4 of the 2009 World Series was the last time CC ever pitched in the Fall Classic. But he was everything the Yankees could have hoped for, and more, in 2009. One year after missing the playoffs the Bronx Bombers were back on top of the baseball world.

On and off the field, CC was indispensable, shutting down opponents while making three consecutive All-Star teams from 2010-12 and functioning as a clear clubhouse leader. That included setting an example for self-care. On the eve of the 2015 postseason, he stepped away from the Yankees to address his issues with alcoholism that were threatening to ruin his life. Sabathia got cleaned up, began a mid-career resurgence upon returning to the team in 2016, and last October, he celebrated 10 years of sobriety.

Sabathia was prepared to exercise an opt-out in that original contract following the 2011 campaign as a negotiating tactic, but the the Yankees were able to avoid it by tacking on an extra year and $30 million. He would later re-sign two more one-year deals to finish with 10 seasons in New York, retiring with 251 career wins (134 of them in pinstripes, 10th on the franchise leaderboard), 3,093 strikeouts, and a place as one of the all-time great Yankees. A year ago, on January 21, 2025, Sabathia sailed into Cooperstown on the first ballot, appearing on 86.8 percent of the ballots and wearing a Yankees cap on his plaque. He entered the Hall with Ichiro, who also debuted in 2001.

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2009 alone was enough to put Sabathia on this list. Everything else was gravy.

References

CC Sabathia. Baseball-Reference.

Chavez, Andrés.“25 Smartest Moves of the Past 25 Years: CC Sabathia signed.” Pinstripe Alley. February 2, 2022.

Hoch, Bryan. “How the Yanks landed CC, 13 years ago.” MLB. December 15, 2021.

Kepner, Tyler. “How CC Sabathia’s 2008 Milwaukee summer smoothed a path to Cooperstown.” The Athletic. July 7, 2025.

O’Connor, Ian. “CC Sabathia’s biggest Yankees win was healing the Derek Jeter-Alex Rodriguez divide.” The Athletic. July 27, 2025.

“Sources: Yanks, Sabathia agree to deal.” ESPN. December 10, 2008.

See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.

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