Derek Jeter predicts New York Yankees and Chicago Cubs in 2025 World Series

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With the MLB All-Star festivities wrapped up in Atlanta and the second half of the season up next, Hall of Famer Derek Jeter made a bold World Series prediction. The former New York Yankees legend didn’t hesitate when asked who he believes will be the last team standing this fall.

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While serving on Fox Sports’ All-Star Game broadcast crew, Jeter voiced his pick with confidence.

"This year, I’m rolling with the New York Yankees," Jeter said following the National League’s victory in the Midsummer Classic at Truist Park.

Historic Final Series

Not only did Jeter select the Yankees to hoist the trophy, but he also picked the Chicago Cubs to come out of the National League, setting up a high-profile Fall Classic.

“Yankees are going to take down the Cubs in the World Series,” he added. “I’m going with New York because [Brian] Cashman said he's going all-in. So I’m expecting a big move before the deadline.”

The message from “The Captain” is clear: Jeter expects the Yankees front office to back up its words with aggressive action ahead of the July 31 trade deadline.

At the break, New York trails the red-hot Toronto Blue Jays in the AL East. The Yankees sit at 53-43, two games behind the Jays (55-41), with Boston also surging on a 10-game win streak to sit just three games out.

New York knows how quickly fortunes can shift. Just last year, the Yankees made it to the World Series but were outmatched in five games by the Los Angeles Dodgers.

Now, led once again by Aaron Judge, the Bronx Bombers are aiming for redemption, and with Jeter’s public vote of confidence, expectations are sky-high.

All eyes now turn to Brian Cashman and the Yankees’ front office to see if Jeter’s World Series call becomes a self-fulfilling prophecy.

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