For the Red Sox, the 2025 season ended on October 2, but the to-do list for 2026 is in full swing. With winter approaching, Craig Breslow is digging into every aspect. In his next season plans, Paul Skenes might make his way in, but in return, a trade might upset the Red Sox’s notion entirely.

Despite the postseason exit, one thing that stands out positively for the Red Sox front office is the arm of Garrett Crochet. However, Breslow knows that Crochet can’t do it all alone. It was proven in the Wild Card series. As he mentioned in his game plan, “They will be as aggressive as they can to acquire another starter to the level of Crochet, but they will also try to work with what they have internally.” He wants someone beside Crochet who can anchor the innings and strengthen the staff, and set the stage for a long-term push in October.

Breslow acknowledged the flashes of brilliance within the current rotation but outlined that consistency remains a challenge. “I think we wanna build the best rotation we possibly can. At times through the year, you could say Bello pitched like a number two, because he did. Giolito pitched like a number two, because he did. Or Connelly Early pitched like a number two, because he did,” Breslow explained.

Building on that context, an interesting trade possibility has come up.

The Pirates’ best pitcher, Paul Skenes, has been suggested as a viable target. Daniel Feininger of BoSox Injection explains that to get Skenes, “Jarren Duran would likely act as the frontline name in any blockbuster trade with the Pirates.” But he also mentioned the Pirates’ stance.

“To be clear, Pittsburgh remains adamant that Skenes isn’t a player up for grabs, but for a course-altering offer, the organization would have to listen.”

Paul Skenes posted a dominating 2025, leading MLB with a 1.97 ERA and recording 216 strikeouts over ~187 innings, while maintaining a 0.95 WHIP. That stat line made him the top choice. On the other hand, Duran, who was once the powerhouse for the BoSox this season, has struggled.

In 2025, he slashed .274/.323/.423 in 297 plate appearances, with 4 home runs, 35 RBIs, and 15 stolen bases.

Even after that, he has been a fan favorite. Earlier this season, around the trade deadline, when rumors sparked about his trade, there were chants outside the stadium when Breslow was leaving, not to trade him. As Feininger also mentioned, “Duran is a spirited cornerstone personality already blossoming into similar folk hero gravitas in Boston.”

While the trade did not happen back then, it might become a reality this time.

But there is more going on than just the Paul Skenes-Duran potential trade. Breslow’s proactive pursuit of pitching is an indication of a bigger change. It means that Boston’s championship window has fully opened.

Building depth and identity, the Red Sox’s offseason roadmap

Craig Breslow thinks this offseason is all about finding balance. It’s not just about repairing what went wrong; it’s also about building on what worked. As the Red Sox try to keep up the good work they’ve done this season, their chief baseball officer feels better about the players he’ll be working with.

Breslow stated at the front office’s end-of-season press conference on Monday, “We’ve talked a lot about how this window of contention is upon us.” His message was clear.

The team is no longer rebuilding. It’s competing, and the next several months will show how ready they are to keep winning in the long term.

He also said that making sure the Red Sox can keep competing will require a whole-system approach. That involves meeting needs without being too focused on one thing.

Breslow aims to strengthen the pitching staff, which was both a strength and a weakness, while also continuing to develop the young position players who made huge steps in 2025.

This plan is closely related to his search for another ace like Paul Skenes, and it also keeps guys like Brayan Bello, Lucas Giolito, and Connelly Early on his side. Breslow wants a long-term solution by adding smart players and letting the team evolve from within.