Ace pitcher CC Sabathia arrives in style, riding his winning ways to Cooperstown

Whether a young star for the Indians or the ace of the Yankees, CC Sabathia won everywhere he played. His winning ways led him to the Baseball Hall of Fame.
By Robert Grayson
JUL 18, 2025
NEW YORK - OCTOBER 16: CC Sabathia #52 of the New York Yankees pitches against the Los Angeles Angels of Anaheim in Game One of the ALCS during the 2009 MLB Playoffs at Yankee Stadium on October 16, 2009 in New York, New York. (Photo by Jim McIsaac/Getty Images)

The way he wore his cap. The way he struck out batters (all 3,093 of them). The way he won big games. No, you can’t forget about all that when it comes to CC Sabathia.

Members of the Baseball Writers’ Association of America (BWAA) certainly didn’t forget when they elected Sabathia to the Baseball Hall of Fame in his first year of eligibility.

“It means a lot just being in the Hall of Fame, period. But on the first ballot—I know what that means to a baseball player, and it’s very special,” Sabathia said.

True, but what stands out most in Sabathia’s splendid 19-year major league career (2001–2019) is his stunning, three-month stint in 2008 with the Milwaukee Brewers. It was a performance that may never be equaled by another hurler.

Sure, he was great with Cleveland, where he won the Cy Young Award in 2007, and with the Yankees, where he won a World Championship in 2009 and was named AL Championship Series MVP.

But has any pitcher ever had a better three-month period with any team and helped them down the stretch more than Sabathia did with the 2008 Brewers? You’d be hard-pressed to find anyone who put up the numbers he did then.

Sabathia was traded to the Brewers from Cleveland on July 7, 2008 and from then to the end of September, he won 11 games, had a 1.65 ERA with seven complete games—including three shutouts—while pitching mostly on only three days’ rest. He struck out 128 batters in 130.2 innings and almost single-handedly carried the Brewers to their first postseason appearance in 28 years.

MILWAUKEE - SEPTEMBER 28: Starting pitcher CC Sabathia of the Milwaukee Brewers pumps his fist after pitching a complete game as they celebrate clinching the National League Wild Card against the Chicago Cubs at Miller Park on September 28, 2008 in Milwaukee, Wisconsin. The Brewers defeated the Cubs 3-1. (Photo by Darren Hauck/Getty Images)

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He simply electrified Brewers fans and the big lefty is legendary in Brew Town to this day.

Even Sabathia himself said, “It was the only time in my career that I went to the mound, every game I pitched, knowing I was going to win. You never have that much confidence. It was like an out-of-body experience. That’s why I wanted the ball so much. It was a lot of fun.”

And why not? Sabathia loves baseball and competing. You could see that whenever he flashed that big smile on the diamond and even in the dugout.

He was a throwback who played the game with passion and craved being around the game. Couldn’t get enough of it. He had his own style, wearing a baggy uniform and his cap tilted to one side. He was in a class all his own, and that included doing something in Milwaukee that you won’t see in any statistics. He pitched on short rest and was a workhorse for a team that had just acquired him, as free agency neared for him at the end of the 2008 season.

While many players would have taken it easy, fearing injury as a big payday approached, the powerful left-hander saw the trade to Milwaukee as an opportunity to show what he could do, the difference he could make. He never lost sight of the goal—“to win.”

His presence in the Brewers’ clubhouse lifted up the whole team, even though, at first, the trade from Cleveland was not easy for the star hurler.

“When I first got the news that I was traded, I was devastated,” he said. “I had been in the Cleveland organization since I was 17 years old. I didn’t know any other organization. I was there for 11 years—eight in the majors—and I really believed I’d be there the rest of my career.”

With the support of his wife, Amber, Sabathia began taking the move in stride, and then he walked into the Milwaukee clubhouse.

“They were in the middle of a playoff run. They were happy to see me. They were very welcoming and there were some players I knew there, like Prince Fielder. They made me feel good and I wanted to win for these guys,” the 6-foot-6 starter recalled.

While Milwaukee lost to the Philadelphia Phillies in the 2008 National League Division Series, the Brewers’ electrifying stretch run, led by Sabathia, and their appearance in the postseason gave fans thrilling memories for years to come.

DOUBLE C

A native of Vallejo, Calif., Carsten Charles Sabathia was given the nickname “Double C” by his friends. The nickname morphed into “Dub” and then “CC.” His close friends still call him Dub.

As a teenager he was a great athlete, playing baseball, football, and basketball, and excelling at all three sports at Vallejo High School. He was selected in the first round of the 1988 MLB Draft by the Cleveland Indians.

Sabathia was a big strong kid, and Cleveland saw star power in the youngster, sending him to the Burlington (N.C.) Indians in the Rookie Appalachian League. The team’s pitching coach, Carl Willis, went to meet the young prospect at the Greensboro airport and that began a lifelong friendship. Willis saw Sabathia’s raw talent immediately and went to work.

When the pitching ace got word that he had been elected to the Baseball Hall of Fame, he was quick to acknowledge a debt to Willis.

“My first impression of Carl was, ‘I love this guy.’ We talked on the way back from the airport and I was ready to go,” the six-time All-Star said. “He [Willis] literally taught me everything I know about pitching, from my delivery to how to approach the game mentally. He taught me how to grip the ball and throw a fastball, slider, and cutter—everything.”

Willis worked his way through the Cleveland organization together with CC and eventually ended up as the big club’s pitching coach in 2003. Sabathia was promoted to the majors in 2001, where he went 17–5 as a rookie and ended up second in Rookie of the Year voting to fellow 2025 Hall of Famer Ichiro Suzuki.

During his eight seasons in Cleveland (2001 to July 2008), Sabathia won 106 games, including 19 in his 2007 Cy Young season. He also won the 2007 Warren Spahn Award, given annually to the best left-handed hurler in the majors. He’d win that award twice more—in 2008, the season he spent with both Cleveland and Milwaukee, and again in 2009 with the Yankees.

DETROIT - MAY 26: C.C. Sabathia #52 of the Cleveland Indians pitches against the Detroit Tigers on May 26, 2007 at Comerica Park in Detroit, Michigan. The Indians defeated the Tigers 6 to 3.(Photo by Rob Tringali/Sportschrome/Getty Images)

During his time in Cleveland, Sabathia also met Jim “Mudcat” Grant, who played 14 years in the major leagues. Grant was the first black pitcher to win 20 or more games in the American League, which he did with the Minnesota Twins in 1965. He won 21 games that year. He started the Black Aces, a group of African-American hurlers who won 20 or more games in a season in the majors. Only 15 African-Americans have accomplished the feat, and Sabathia did it in 2010 with the New York Yankees, winning 21 games—the most in the majors that season.

Only three members of the Black Aces are in the Hall of Fame—Bob Gibson, Ferguson Jenkins, and Sabathia.

“I didn’t understand what it meant for a black starting pitcher to win 20 games. He [Grant] made sure I understood what it meant and pushed me to accomplish the feat. I was happy to have him in my life and to fulfill this dream,” Sabathia said.

YANKEE WINNER

Following his stellar three months with the Brewers, Sabathia became a free agent. He had many suitors, and finally signed with the Yankees. But he had some hesitancy about playing in the Big Apple.

“I was coming from a small market and there are high expectations from fans in New York. Also, I heard there was turmoil in the Yankees clubhouse,” the 44-year-old Hall of Famer said. “But [Yankees general manager] Brian Cashman convinced me that the Yankees really wanted me and one of the reasons was for my leadership in the clubhouse.”

Sabathia’s wife Amber was involved in the decision too, reminding CC that he was a big part of why the Cleveland clubhouse was so much fun and why the team did so well when he was there.

There was something else that kept gnawing at him too.

“If you want to be a winner, how could you not want to play for the Yankees?” he said. “They are the only organization committed to winning every year. They go to spring training every year knowing that, to be successful, they need to win the World Series.”

Once Sabathia got to his first spring training with the Bronx Bombers, he knew he’d made the right decision. He struck up a friendship that still lasts to this day with another pretty good lefty—Andy Pettitte. Derek Jeter wasted no time greeting him and becoming friends.

NEW YORK, NY - JUNE 09: (NEW YORK DAILIES OUT) CC Sabathia #52 and Derek Jeter #2 of the New York Yankees in action against the Boston Red Sox on June 9, 2011 at Yankee Stadium in the Bronx borough of New York City. The Red Sox defeated the Yankees 8-3. (Photo by Jim McIsaac/Getty Images)

Being around the Core Four (Pettitte, Jeter, Jorge Posada and Mariano Rivera) “was all really cool. The pitchers would all go out to dinner together. We had a great team and a great camaraderie. It was the right place for me,” Sabathia fondly recalled.

With the Yankees (2009–2019), Sabathia won 134 games and struck out 1,700 batters. He went to the postseason with the Yankees seven times, including that championship year in 2009. He will be shown wearing a Yankees cap on his Hall of Fame plaque.

Though Sabathia said he is proud of and grateful to all the organizations he played for during his career, he found a home in the Bronx. Oh, and one more thing about the big fella: He was durable. Sabathia pitched just over 3,577 innings in his career, including 13 seasons with 180 or more innings. That’s a workload that many of today’s young starting pitchers may never equal or come close to in their careers.

That stat alone is worth a tip of the cap, whether you wear that cap tilted to one side or not.

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