FOX MLB Crew Predicts Bold Trade Deadline Will Decide World Series Teams

The first half of MLB’s 2025 season is over, and the All-Star Game is behind us, as well. What better time to start looking at just which teams might be in this year’s World Series than now? 

FOX’s Kevin Burkhardt posed the question of World Series favorites to fellow analysts and former MLB players Derek Jeter, David Ortiz and Alex Rodriguez at the conclusion of the 2025 MLB All-Star Game, and there was a theme worth exploring: the trade deadline.

All three of Jeter, Ortiz and Rodriguez emphasized the importance of the trade deadline in ensuring that their predictions come to pass. Jeter even prefaced his pick with a callback to last year. “Last year I picked the Baltimore Orioles to go to the World Series,” Jeter told Burkhardt. The reason why I picked them is I was looking forward to the trade deadline, Baltimore had a stacked minor-league system, I thought they were going to make a move, they didn’t do it, they didn’t win.” 

This year, he used the same strategy, but for the Yankees. And Jeter isn’t expecting a repeat of last year’s Baltimore inactivity, either. “So this year I am going with the New York Yankees. Yankees are going to beat the Cubs in the World Series. I’m going with the Yankees because [Brian] Cashman basically said that he’s all-in. So I expect the Yankees to do something at the trade deadline.”

As for Ortiz, he once again went with the Red Sox as his pick for the World Series champion, citing their recent success – the Red Sox entered the All-Star break riding a 10-game win streak – as well as expected trade deadline activity as the reasons. “Can’t get no better than that, you go into the trade deadline, we pick some stuff, get the team better, and all of a sudden, winner in Boston.”

Rodriguez had less confidence in a specific pick than either of Jeter or Ortiz, citing the “wide open” field of potential World Series candidates. “We’ve been doing this now for 10 years, and this is the one year, fellas, that’s wide open. I have no idea who’s going to go to the World Series, and that’s a good thing.” Rodriguez continued on, however, citing the potential of the trade deadline as a separator, just as Jeter and Ortiz had.

“There’s going to be a competition of the best front office that does the most bold moves in the trade deadline, and I’m going to go with the most resources: Yankees and Dodgers,” said Rodriguez. “All the eyes will be on Brian Cashman, to make the moves to finally get over the L.A. Dodgers in October.”

Two picks for the Yankees – one over the Cubs, one over the Dodgers – and one for the Red Sox against whichever team they come up against. All of these selections, however, rely on these clubs doing what the Orioles didn’t do either for themselves or for Jeter a year ago: getting even better than they already are at the July 31 trade deadline. 

The Yankees, as of the break, are in second place in the AL East, two games back of the Blue Jays, while the Red Sox are in third, three games back. Both have wild cards in their possession, though, and there’s a lot of season left that includes a trade deadline in it, too.

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