The Pesky Report (Red Sox Podcast)🎙

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.Make sure to follow us on Twitter, Instagram, & Facebook @PeskyReport.We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ 

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 Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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?Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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. Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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.Make sure to follow us on Twitter, Instagram, & Facebook @PeskyReport.We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ 

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.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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!Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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. Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

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.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

Matthew and Doink break down the most recent series against the homeless Athletics. There was only one win, but a few smaller victories through the series, like Justin Slaten and Payton Tolle’s performances in the Pen. Nate Eaton continuing to crush opposing pitchers but usually having a moment of dumb in there you didn’t see coming. They talk about Hogdale’s success and how awesome it is to see the former Pesky Report alumn’s ascension. They also look at the upcoming matchups and what its going to take to lock down this playoff spot.Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

The MiLB Talk crew is joined by ANOTHER special guest this week. This time it’s Boston Red Sox third-round draft pick Anthony Eyanson. The right-handed pitcher talks about his College World Series run at LSU, his time in the Cape Cod league, and what’s he’s done with the organization since being drafted. They also ask him about the draft process, his pitch mix, and what his first time in Boston was like. They find out what his walkout song would be if he came out of the bullpen, his pregame process, and more. Jake, Derrik, and Hunter then discuss the week of baseball for Worcester, the season ending for Portland, and the AFL rosters.Make sure to follow us on Twitter, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

Jordan, Jack and Brian recap a weekend series with the Yankees that saw the Sox lose two of three.The gang talks through what's been a massive struggle offensively since the Roman Anthony injury, but the pitching hasn't been perfect, putting the team in a first-inning hole each of its three straight losses.Later, more lockout talk! Then a little "Tolle or Early" debate before Jordan's caffeine rush kicks in when the trio previews the upcoming series with the Athletics.Make sure to follow us on Twitter, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

Matt, Bayleigh and Isiah talk about where the Red Sox are at with two weeks left in the season, they talk about Connelly Early’s debut and Garrett Crochet’s dominant outing. The group looks at how the lefty pitchers they have could be deployed in the playoffs to take that 4th rotation spot. They also talked about the offseason roster logjam that will start the second the season is over, with all the 60 day IL guys needing to be placed back onto the 40 man.Make sure to follow us on Twitter, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

Jake, Derrik, and Hunter are joined by a very special guest for MiLB Talk this week. Boston Red Sox Senior Director of Player Development Brian Abraham. Abraham explains his longtime connection with the team, what he does and where he travels for his job, and more. We hear about team philosophies, analytics, and external hires. Abraham explains the process of promotions and trades. He also discusses Kristian Campbell, Yhoiker Fajardo, Franklin Arias, Justin Gonzales, and a few other top prospects. The trio hit their usual MiLB rundown as well.Make sure to follow us on Twitter, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

Jordan and Jack recap a very upsetting series for the Boston Red Sox against the Arizona Diamondbacks. Despite the shorter episode, the duo discuss Payton Tolle's struggles, as well as continued slumps for Alex Bregman and Masataka Yoshida.They also revel in Jack's agony as someone who wanted the Red Sox to draft infielder Jordan Lawlar back in 2021 before moving on to talk some more about the dominance of 2025 Aroldis Chapman.Lastly, they talk about the Ballpark Karen in Miami before previewing the upcoming series in Sacramento with the Athletics.Make sure to follow us on Twitter, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg

Matt and Doink break down a series victory against the Guardians that doesn’t feel so joyous on the tail of the news that Roman Anthony will miss the rest of the regular season due to injury. They look at the ideal playoff roster given how this impacts things, and how the lineup will need to produce without him. They talk about Zack Kelly looking good as the bulk reliever, and Hicks to the IL. They also talk about the best plan being to just win out.Make sure to follow us on Twitter, @ThePeskyReport. We are officially a part of Beyond The MonsterTwitter: @BeyondtheMnstrSubstack: https://beyondthemonster.substack.com/ Intro Music: DannyEBTracks https://www.youtube.com/channel/UCxOQyRmgJqHji6ItvllZmYg