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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Matt, Jordan and Isiah break down the final series of the 2025 Boston Red Sox, as they’ve been eliminated by their archrival New York Yankees in three games of the American League Wild Card Series. The trio doesn’t spend a whole lot of time talking about the series, instead pivoting towards offseason dialogue. Just how obvious are the fixes? Would you trade Ceddanne Rafaela?

Jordan also poses the question of, knowing what we know now, would Red Sox fans have been happier with Nick Pivetta returning in 2025 if it meant keeping Rafael Devers opposed to what potentially may be only one season of Alex Bregman in Boston.

Finally, the group picks their World Series winners before closing out the final episode of the 2025 season.

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Jordan, Jack and Brian recap the one game that mattered in the Tigers series before doing some 2025 superlatives and previewing the upcoming Wild Card Series in the Bronx.

Lucas Giolito will miss it with an elbow issue that required him to see an orthopedic surgeon.

How much cause for concern is there? How close is Marcelo Mayer to returning? Roman Anthony? All questions pondered and answered in this 100-minute episode of The Pesky Report!

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Matt, Doink and Isiah break down the series victory against the Blue Jays. Magic number to clinch is now 1. They go over the different scenarios that it would tae to clinch, they also talked about Trevor Story’s most recent decline in defense. Alejandro Kirk is so slow and Wilyer  throwing him out from RF to end the game was so funny. They also go over injury updates for Anthony, May, and Hicks. The crew also looks at Crochet’s start and what a great season he’s had. Also some talk about Salem at halloween.

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Jake, Derrik, and Hunter return for the MiLB award show and the 100th episode of MiLB Talk. They discuss the final week for Worcester and the Triple-A debut of top prospect Luis Perales. The trio hands out awards throughout the minor league system including best pitcher, best slugger, and best Major League debutant. There are a few surprise winners, and some blatantly obvious picks, but everyone gets some love. Jake gives us the top 10 moments in MiLB Talk history to celebrate 100 episodes. The show ends with the season finale of guess the prospect as a two-man round mixes things up.

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Jordan, Brian and Jack recap a series win in Tampa Bay for the Boston Red Sox. The trio looks at this team’s recent stretch of play and questions the ceiling of this group, but remain confident in its ability to make it to the postseason. Alex Bregman and Masataka Yoshida are both showing signs of life, Jarren Duran has the swing of the season and Kyle Harrison flashes brilliance in his first Red Sox start.

Later, they take a look at the division race, which isn’t quite wrapped up as Boston will head to Toronto this week to face the Blue Jays.

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