Alex and Maddie are joined by guest Richard McGill of Playing Catch to discuss the trade that sent Sonny Gray to the Red Sox. They talk through some NL Central trade options and close out with why Red Sox fans will be excited to have Gray on the team in 2026.

Maddie and Alex run through the roster changes as the Red Sox prepare for the Rule 5 draft. They then discuss Kristian Campbell's new position in left field and turn that into a discussion on Jarren Duran trade packages. They wrap up the episode by running through the Pete Alonso rumors and discussing other potential free-agent fits.

Alex and Maddie are back after the World Series to give an offseason primer and talk about just why this free agent class could be considered lackluster. They speculate what Triston Casas could be talking about in his most recent, very cryptic, Instagram post, and then talk through pitching trade ideas. They wrap up talking about the still-clogged outfield and what the remedy for that situation could be.

Maddie and Alex join to talk about the heartbreaking loss as the Red Sox were shut out against the Yankees in game three of the Wild Card round.

Alex, Maddie, and Brock talk about the late-inning loss against the Yankees, forcing a must-win situation in game three at Yankee Stadium.

Alex and Maddie are joined by Brock Beauchamp to talk about the closely-fought Red Sox win over the Yankees in game one of the Wild Card round.

Maddie and Alex discuss Roman Anthony's oblique injury and timeline, wondering how exactly the team will handle his return. They then dive into the latest Alex Bregman contract news and start to wonder what the team may look like next year with his potential absence. They pick up the attitude with a look into Payton Tolle's first start and the domination that led to Aroldis Chapman's surprise extension. Finally, they end the show with a sincere thank you to the fans who have made the last year of Talk Sox possible.