The New York Yankees entered the 2025 season as a World Series favorite. Despite not winning the American League East division, the expectations are unchanged. After barreling through the rival Boston Red Sox in the Wild Card round, the Yankees are set to face off against another division rival in the ALDS — the Toronto Blue Jays.
During the weekend's slate of games, Yankees legends Derek Jeter and Alex Rodriguez revealed their World Series predictions. The result was unsurprising.
Jeter, flanked by his MLB on Fox colleagues, stuck to his previous World Series prediction, picking the Yankees and Chicago Cubs to meet in the Fall Classic.
“I’m sticking with my pick at the All-Star Game: Yankees over Cubs,” Jeter said. “I know it’s not looking too good right now [after the Cubs' 9-3 loss vs. Brewers], but the Cubs need to get past Milwaukee, and hope that [Phillies] and the Dodgers beat each other up.”
Jeter's prediction is bold, at least on the National League side. Whereas the former Yankees shortstop picking the Bronx Bombers to win it all is as close to a homer pick as possible. The last time the Yankees and Cubs met in the World Series was 1938. New York swept the series in four games.
🚨 It's World Series predictions time! 🚨@DTrainMLB: Dodgers over Yankees @derekjeter: Yankees over Cubs@AROD: Yankees over Phillies@davidortiz: Dodgers over Mariners pic.twitter.com/fnFGSH3xzo
— FOX Sports: MLB (@MLBONFOX) October 4, 2025
While Jeter chose a World Series matchup not seen for 87 years, Rodriguez elected to pick a more recent classic to revisit and sprinkled in another hot take for good measure.
“I think finally, this is the year that big [Aaron] Judge has a signature October,” Rodriguez said. “I’m going to go with a rematch of the 2009 World Series. Yankees over Phillies. World Series MVP Aaron Judge. Yankees in six [games].”
The teams picked are not shocking, but predicting Judge to break out of his career-long postseason slump is.
In 61 career postseason games, Judge is hitting a putrid .212 with 16 home runs and 35 RBIs. However, there are signs the two-time MVP is starting to lay to rest his October demons.
In the three-game Wild Card series win over Boston, Judge tallied a .364 batting average and a .780 OPS. While the power has yet to emerge, Rodriguez might be onto something picking Judge to win World Series MVP. That is, if the Yankees can get past the Blue Jays, who won the season series 8-5.
