Matt, Derrik, and Jordan are joined by Worcester Red Sox broadcaster Mike Antonellis to talk about the Boston Red Sox offseason. There's finally some offense to talk about, as the team acquired first baseman Willson Contreras for three pitchers.

Later, the group discusses the beauty of Polar Park and some of the coolest players he's covered in his 20 years with the Red Sox organization.

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Jordan, Derrik, and eventually Jason, do a near three-hour stream to vent about the Red Sox offseason thus far. They talk about how to salvage the offseason, if there are avenues we haven't considered, etc.

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Jake, Derrik, and Hunter are back for a “normal” episode of MiLB Talk. They look into the Winter Meetings, the Rule 5 Draft results, and all the craziness that goes with it. The Red Sox made multiple trades, so we have plenty to talk about. They discuss all the catchers Boston has added in the system, as well as the pitchers moved and how the organization is still loaded with arms.

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Matthew, Jordan, and Hunter are joined by Boston Red Sox rookie Payton Tolle. The trio talk to Tolle about his MLB debut and his road to Fenway. Tolle gives us his thoughts on teammates, the rivalry, celebrations, TV shows, movies, and more. Boston

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Jordan, Doink and Jason recap the Winter Meetings, which was pretty active; just not involving the Red Sox. Pete Alonso signed a five-year contract with the Baltimore Orioles worth over $150 million. As a result, Red Sox Twitter reacted accordingly.

They also did the same when Kyle Schwarber signed a five-year deal with the Philadelphia Phillies.

How will the Red Sox pivot? How confident are we in such a pivot?

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Jordan, Jake, and Hunter are joined by Boston Red Sox prospect Caleb Berry. They discuss his wild journey to make it to minor league baseball, and how he’s felt while joining the Red Sox organization.

He gives us a rapid reaction to the trade that sent his teammate Jesus Travieso out of town. They find out who got him into the game of baseball, who he modeled his game after, and what he wants to accomplish this offseason.

Berry tells us what his day-to-day is, thoughts on some teammates, and what he wants to improve on.

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Matt, and Jordan are joined by Robbie Hyde of “Monster Territory” to break down the latest offseason news surrounding the Red Sox, and find out what is the ideal offseason plan for Robbie to make this team a World Series Contender. From Ketel Marte to Tarik Skubal what would trade packages look like and does that even make sense? Will the Red Sox acquire another front of line starting pitching besides Sonny Gray. Who is more likely to be traded, Duran or Abreu? Also change your twitter passwords everyone and #staysafe out there.

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Jordan, Kev, and Bayleigh give their initial reactions to the Sonny Gray to Boston trade. Is he the team's No. 2 starter? Can they be a World Seres contender if he is? Does anybody they acquire outpitch what they got for three months out of Brayan Bello and Lucas Giolito in 2025?

They also give their thoughts on the Toronto Blue Jays signing right-hander Dylan Cease to a seven-year deal worth $210 million. That team is finally being rewarded for its efforts in becoming a big-market club; only heightened by the recent run to the World Series.

Lastly, the duo talks more impending Collective Bargaining Negotiations. Will it be all hype? How much baseball are we losing in 2027.

All that, and more, in this edition of The Pesky Report.

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Jake, Derrik, and Hunter are joined by Tyler Milliken of the Section 10 Podcast to talk all things minor league baseball. They talk about the new Single-A identity, the upcoming Rule 5 Draft, and who could be moved. Milliken gives his thoughts on potential trade options, Kristian Campbell, and the pitching depth in the organization. They talk about past moves, where the organization is going, and what prospects Milliken is most looking forward to watching in 2026.

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Pod By The River Host and former Pesky Report Alum Ed Hand joins the show to talk about his Free Agent Tracker ahead of the 2025-26 MLB Offseason!

The trio discusses Ed's tracker, including the genesis of his work, getting asked about doing it again, and the difficulties that come with doing so.

They also talk about some under-the-radar players on this ranking, including at the deep position of first base.

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