
Whether it comes to free agent signings, trades or extensions, this feels like one of the most consequential offseasons the Red Sox have had in a very long time.
After advancing to the postseason for the first time since 2021, Boston was bounced in their three-game wild card series with the Yankees at Yankee Stadium - an especially disappointing result given they were the first team to lose a Wild Card Round since the format change in 2022 after leading the series 1-0.
They ran out of starting pitching. They stopped hitting across the board. The team was completely out of gas.
Even with the air coming out of the balloon, this team showed they have a strong foundation to build on moving forward:
- Young outfielders winning Gold Gloves
- A generational hitter at the top of their order
- A Cy Young-level talent at the top of their rotation
- A young catcher who profiles as one of the best offensive players at his position
Add in a fringe Hall of Fame closer coming off the best statistical season of his career, and you can understand why the Red Sox have the seventh-best odds to win the World Series in 2026.

With that said, they have important decisions to make at both ends of the spectrum. They need to decide how they’ll go about addressing their needs at starting pitching and power hitting, and they need to decide which players on the fringes of the roster are going to be a part of the future of this team.
In the early going this hot stove season, they’ve already been incredibly busy:
Here’s a sampling:
- RP Chris Murphy traded to White Sox for C Ronny Hernandez
- RP Luis Guerrero traded to Tampa Bay for IF Tristan Gray
- Sox DFA Nathaniel Lowe to make room for Gray on 40-man roster
- Sox likely to tender contract to SP Tanner Houck
- RP Bernard Bernardino traded to Colorado for IF/OF Braiden Ward
Amidst all this activity, in steps Steve Phillips, a former general manager with the Mets from 1997 to 2003 who has now been a longtime MLB analyst on TV and radio - first for ESPN, and now for MLB Network.
Here’s what he said when asked about why he's bullish on Boston this hot stove season:
Question: Let's talk a little bit about the Red Sox. You know, we like to identify teams at the beginning of the hot stove season that have payroll canvas, that have needs that might be on an uptick. Boston exceeded expectations last year. You feel like they're primed to make an even bigger move in ’26. Why?
Steve Phillips: “Yeah, because if I'm buying stock, I'm buying Red Sox stock right now. They've got financial flexibility after moving Rafael Devers and with [Alex] Bregman now coming off the books. Sure, they've got a hole to fill there, but they could sign Bregman and sign Pete Alonso and still be within the money of what they had on their budget this year for Bregman and Devers. And so they're in a great spot.
“They've got money to spend. They've got major league depth and surplus in the outfield that if they want to trade, people covet their outfielders. And they've got a terrific farm system as well. Any deal that's out there in free agency, they could sign the guy. They could be the highest bidder. Trade deal - they've got major league players if that's what you want. You want prospects? They've got that too. They can be on everybody. I love where the Red Sox are positioned right now. And, a playoff team in 2025, and I think they could be really good in ’26.”
From your lips to John Henry’s ears, mate!
Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.