CC Sabathia’s World Series pick was defensible. His rationale, not so much.
Sabathia, the Hall of Fame pitcher who served as a studio analyst for NBC Sports’ coverage of the MLB wild-card round, picked the New York Yankees to beat the Milwaukee Brewers in the 2026 World Series on Thursday, Oct. 1.
The Brewers won a franchise-record 103 games to capture the No. 1 seed in the National League. The Yankees dominated the Red Sox in their two-game series. And that was without Aaron Judge, the two-time defending American League MVP, who could return for the AL Division Series. The two teams could easily find themselves playing for a championship in a few weeks.
MORE: NBC’s Joey Votto jinxes Phillies just before Ozzie Albies homers for Braves
Pressed by NBC studio host Ahmed Fareed to explain, Sabathia said, “I’m trying to get my two teams to the World Series.”
Just one problem: Sabathia spent the first 10 years of his career in the Cleveland organization before moving on to Milwaukee and New York. Not only did he ignore that fact, but the Guardians are still playing in the postseason and host the Chicago White Sox in a best-of-five AL Division Series.
For the record: Sabathia picked his first team to lose to the White Sox, even though they finished second to the Guardians in the AL Central during the regular season.
MORE: Jason Benetti goes viral for getting roasted by crew during live broadcast
‘Drafted by perfect organization’
Cleveland pitcher (52) CC Sabathia pitches against the Baltimore Orioles in the fifth inning at Camden Yards in Baltimore. Mandatory Credit: James Lang-USA TODAY Sports Copyright © James Lang Credit: IMAGN IMAGES via Reuters Connect (Reuters)
It was a surprising oversight, considering Sabathia has praised his formative years in the Cleveland organization as being instrumental to his 19-year career.
“I wouldn’t have lasted two years in the big leagues if I were [drafted] anywhere else but Cleveland,” he said in a 2021 interview. “I truly grew up there. I got to Cleveland and I was still a boy. I was 17 years old. I got to the big leagues at 20. I’m still close to so many people in the organization. From old teammates to their old GM Mark Shapiro to even the clubhouse attendants; in a sense they raised me.
“I got drafted by the perfect organization.”
MORE: Former Yankees, Blue Jays, Twins pitcher dies at 70
Memorable, yet short, stint in Milwaukee
The ending to Sabathia’s time in Cleveland was colder and more abrupt. After he and the team couldn’t agree on a contract extension, Clevleand traded Sabathia to the Brewers at the 2008 deadline. He proceeded to go 11-2 with a 1.65 ERA in 17 starts (including three on three days’ rest). He led the Brewers back to the playoffs for the first time in 26 years.
That half-season in Milwaukee left an impression on Sabathia — considerable enough, apparently, that it influenced his 2027 World Series pick. Sabathia’s lone World Series and only championship came as a member of the 2009 Yankees.
Cleveland hasn’t won a World Series since 1948. Its recent Hall of Fame inductee is apparently in no rush to get the Guardians back to the promised land.
— Enjoy free coverage of the top news & trending stories with The Big Lead Newsletter —