Derek Jeter Picking Yankees to Win 2025 World Series over Cubs Has Fans Trolling Him: “As Clueless as They Come”

Former New York Yankees captain Derek Jeter has predicted his ex-team to win the World Series this year over the Chicago Cubs.

Derek Jeter Picking Yankees to Win 2025 World Series over Cubs Has Fans Trolling Him: “As Clueless as They Come”

Former New York Yankees star Derek Jeter (Image via Imago)

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Following a stunning 2025 All-Star game, Derek Jeter made a huge prediction. The former New York Yankees captain picked his ex-team to go to the World Series once again this year and win it all over the Chicago Cubs.

During his time with the team, Jeter won the World Series 5 times and established himself as one of the greats of the game. Since his retirement from the sport, he has worked as an executive and now works as an analyst for Fox Sports.

On Tuesday, alongside Kevin Burkhardt, Alex Rodriguez, and David Ortiz, the ex-shortstop picked the Yankees as the favorites for the World Series. He expressed that the team’s general manager, Brian Cashman, spoke on making some moves during the trade deadline and is thus expecting the team to make a charge this year.

This year I am going with the New York Yankees. I’m going with the Yankees. The Yankees are going to beat the Cubs in the World Series. I’m going with the Yankees because (Brian) Cashman basically said they were all in, so I expect the Yankees to do something at the trade deadline.

Last year, Jeter had picked the Baltimore Orioles to go and win the whole thing. However, the O’s suffered a wild-card round exit at the hands of the Kansas City Royals. They were 2-0 in that series and failed to win a single postseason game for a 2nd year running.

The Yankees, meanwhile, did reach the World Series last year. In their first trip to the Fall Classic since 2009, the Bronx Bombers got dominated by the Los Angeles Dodgers and lost the best-of-seven series 4-1 in 5 games.

Social media reacts to Derek Jeter picking Yankees to win World Series in 2025

This year, Derek Jeter has backed his former team, the New York Yankees, to go on and win the World Series. This prediction from him has seen several users on social media taking a swipe at him and trolling him.

Former New York Yankees star Derek Jeter
Derek Jeter (Image via Imago)

Many users on X made fun of this prediction from the Yankees’ great. One user on X wrote, “Jeter is as clueless as they come” while reacting to this.

Check out that and some other reactions from X below:

Jeter, though, was not the only one who picked the Yankees to prevail this year. His former teammate Alex Rodriguez also backed the Yankees to win this year. A-Rod predicted the Yankees to take revenge against the Los Angeles Dodgers this year and bring home the title. Meanwhile, David Ortiz picked the Boston Red Sox to go all the way this season.

Yankees manager Aaron Boone optimistic of chasing World Series title this year

After a crushing defeat at the hands of the Los Angeles Dodgers in the World Series last year, the New York Yankees started off the 2025 season with a bang. While they have fallen off a bit in recent weeks, manager Aaron Boone has remained optimistic about chasing a World Series title.

Aaron Boone was managing the American League in the All-Star Game
Aaron Boone (Image via Imago)

Since a 1-0 win over the Kansas City Royals around a month ago, the Yankees have had mixed results. They have gone on two separate 6-game losing runs.

This run of form has led to many demands for a change in leadership of the Yankees and the firing of Boone. Following a historic performance from Cody Bellinger in the first game against the Chicago Cubs, the Yankees dropped the series by losing the next two games and entered the All-Star Break on a 2-game losing run.

In a recent press conference, the Yankees manager backed his team and pointed out that there is still a long way to go in the season.

There’s been a lot of good. There’s obviously been two weeks where we really struggled. But we set out in Spring Training and the start of the year to get back to the playoffs and go chase after a world title. All those hopes and dreams are right there and still exist for us. … A long way to go. Still got to keep getting better. But we’re in position to do what we need to do.

The Yankees, who are 2 games behind the Toronto Blue Jays in the AL East Standings, will begin the 2nd half of the season with a 3-game series against the Atlanta Braves in Atlanta. After that, they will travel north of the U.S. border to face off against the Blue Jays in a 3-game series. That series could have huge implications on the division standings.

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