Alex and Maddie discuss the Willson Contreras trade and the impact it may have on Triston Casas. They go through the remaining free agent options for both second and third base before moving on to the starting pitching market. They close the episode discussing possible trade scenarios and give their takes on whether the Red Sox will sign either Tatsuya Imai or Kazuma Okamoto.

Maddie and Alex talk about the uneventful Winter Meetings and why the market for the three top Japanese players (Munetaka Murakami, Kazuma Okamoto, Tatsuya Imai) has been so quiet to this point. They give their takes on if Alex Bregman is really looking at the Diamondbacks as an option and end the episode talking through pitcher trade proposals.

Alex and Maddie celebrate the one-year anniversary of the Talk Sox Podcast by analyzing why Cole Ragans makes a lot of sense for the Red Sox. They then talk through whether the team is overvaluing Jarren Duran and discuss whether he should be traded over Wilyer Abreu. Finally, they talk through the latest news, connecting the team to Ketel Marte. Thanks to everyone who has made this last year a success here on the Talk Sox Podcast!

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.