3 dream offseason moves the Phillies can make to win the 2025 World Series

Is it possible for a team to overachieve and then underachieve in the same season?

The Philadelphia Phillies weren't expected to win the NL East, but they completely dominated the division from start to finish. They dominated the All-Star Game by putting in more pitchers than any other team in history in 2024. But when the playoffs rolled around, the Phillies underachieved.

In the postseason, the Phillies were the only team that received a bye that didn't make the Championship Series. In fact, the Phillies lost their season to their division rivals, the New York Mets.

If the Phillies want to get revenge on the rest of the National League and compete for the World Series, these dream offseason moves would be great steps in the right direction.

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3. Top prospect Andrew Painter would be the pitcher that Philly needs

All season long, the Phillies had an issue with the fifth starter spot in their starting rotation. All season, it was Taijuan Walker, who was an incredible letdown compared to the four All-Star starters that the Phillies had in front of him. Heading into the offseason, the Phillies need to upgrade their rotation, and, lucky for them, they have the perfection option in-house already.

Andrew Painter.

Painter is coming off Tommy John surgery in 2023, but he's finally made his way back to the mound late in the baseball season. Now, Painter has the entire offseason and Spring Training to get his arm and body into shape to crack the big league roster.

He was on pace to make the roster in 2023 before the injury. If he returns close to the player that he was before the injury, he should have a great Spring Training which could land him claiming the fifth starter spot on the Opening Day roster.

The Phillies need to make a spot for Painter on their roster next season, if he's healthy and capable. He's such an incredible talent. If he can get healthy and dominate like he has in the past, he will be a huge upgrade for the Phillies.

2. Philadelphia needs to re-sign key bullpen pieces this Winter

The Phillies bullpen had a ton of excellent pieces this season, including multiple All-Stars. Philadelphia even went out at the trade deadline and acquired multiple more relief arms to try to bolster what they had at the backend. But heading into the offseason, Philadelphia has two key pieces of their bullpen entering free agency.

Their two upcoming free agents are Jeff Hoffman and Carlos Estevez. These two were some of the better right-handed relievers in the entire league last year, though Hoffman fell apart in the postseason. But the Phillies need to do everything in their power to bring these two relief pitchers back in 2025.

Not only do they need to bring them back, but they need to bring them back on multi-year contracts, while also pursuing another reliever if they can find the money for it. They would be putting together a bullpen that can compete with the Guardians for the best complete unit in the entire league. All they would be missing is the closer that puts up a sub-1.00 ERA. If they can run into that generational closer, while bringing Hoffman and Estevez back, they would be in very good shape.

1. Acquiring both Garrett Crochet and Luis Robert would be the dream blockbuster trade

The number one dream move for the Phillies to make this offseason is the exact same move that they were anticipated to make all season long, but never pulled the trigger on.

It's trading a boatload of prospects to the Chicago White Sox to bring in Luis Robert or Garrett Crochet. Or, in this dream world, both of them.

Now, I understand that this would be a huge package of prospects that it would take to acquire these two young talents, but it would be worth it. Robert would fill the team's biggest hole in the outfield while Crochet would slot into the rotation in a perfect way.

Both players come with multiple more years of team control while also being very young. If the Phillies had to choose between the two, it would be Robert that they should prioritize, simply because of the pitching that they have at the top of their farm system. Their rotation would be perfect with their four All-Stars and Andrew Painter.

Robert will be much cheaper in the offseason than he was at the trade deadline. He could very easily be dealt during the Winter months and if the White Sox are shopping him, the Phillies need to be at the front of the line yet again.