The Pesky Report (Red Sox Podcast)🎙

THE BOSTON RED SOX ARE BACK!!! Jordan and Isiah preview the 2026 Boston Red Sox season, as the opener in Cincinnati is finally here. The two of them talk about players they think are poised for big seasons, as well as players who may disappoint. Disclaimer: Lots of talk about eating shoes. They also examine a few fascinating roster plot holes, including potential pathways for Willson Contreras to...

Jake, Derrik, and Hunter are back for the official start of the MiLB Talk season. Andrew Parker of SoxProspects joins the show to discuss the Spring Breakout game and preview the Triple-A Worcester Red Sox 2026 season. Jake says his semi-goodbye (we’re going to make sure he joins as much as possible). We start with a rant on the MASN broadcast, before gushing over Anthony Eyanson. Andrew tells us...

Jordan, Jason, and Kate recap a tremendous World Baseball Classic, which saw Venezuela knock off the United States 3-2 in the Championship. The trio talks about where the U.S. lacked in this tournament, despite being there in the end. They also talk about the upcoming Olympic Games, and how Team USA should be constructed going forward. Later, they talked about the Colorado Rockies for a bit before...

Jordan and Jack talk about their first impressions of the Boston Red Sox in spring training. However, it's tough to form strong opinions considering half the roster is in the World Baseball Classic. However, who is standing out in a positive way? Negative? Is Jovani Moran going to be an inadvertent x-factor this season? How do we feel about there still being an outfielder surplus? What does th...

Jordan and Matt are joined by Ari Alexander (MLB Insider, Sports Reporter for 7 News Boston) as they discuss spring training storylines to watch, Breslow’s comments about Bregman “If he wanted to stay.” They break down the addition of Caleb Durbin and IKF compared to the hype at the start of the offseason, as well as talk about Breslow’s comments about acquiring a big bat and then not doing so. Th...

Jake and Hunter are joined by Boston Red Sox prospect and AFL All-Star Stanley Tucker. The duo ask Tucker about missing the 2025 season, his AFL All-Star run, and his goals for 2026. They find out where he wants to play, teammates he’s formed a bond with, and veterans who have helped him. Tucker talks about his journey to this point, from High School to professional ball and how things changed for...

Mikey Romero joins Matthew and Hunter for his third appearance on The Pesky Report. The Boston Red Sox prospect talks about his value in the system, his experience with Camp Story, Chad Tracy returning, and more. He tells us about his offseason, his goals for 2026, and stories of trades. He gives us a little insight into his eating habits and his baseball cards. Make sure to follow us on Twitter,...

THE BOSTON RED SOX SIGNED A FREE AGENT!!!! Craig Breslow's first move of free agency nets the Red Sox left-hander Ranger Suarez. The former Philadelphia Phillie has a 3.38 career ERA in 762 career innings of work. He's also one of the game's best postseason pitchers, posting a 1.48 ERA in 42.2 career playoff innings. Jordan, Jason, and Jake give their initial reactions, as well as talk...

Jordan, Bayleigh, and Hunter are here to rant about the Red Sox losing out on Alex Bregman. The Chicago Cubs swung in with a big offer and we have to deal with the fallout. How does everyone feel about the offseason? Where do the Red Sox pivot to now? Is Craig Breslow any different than Chaim Bloom? We reopen the can of worms that is the Rafael Devers trade again. The trades have been positive thi...

Matthew, Jason, and Hunter are joined by Boston Red Sox prospect Henry Godbout. The 2025 draftee talks about his draft process, growing up a Red Sox fan, and his first taste of the organization. He tells us about his pregame routine, looking up to Dustin Pedroia, and his not-quite home run. Godbout gives us his offseason goals and what he’s hoping to achieve in 2026. Make sure to follow us on Twit...

This is Round 2 of the Pesky Report Expansion Draft, with Derrik Maguire and Jason Stellakis squaring off as our general managers. The Utah Talons and Nashville Bandits are our two teams. Round 2 is 20 picks, with each GM taking 10 players. Their GMs finish crafting their teams through the draft, and then putting a bow on the roster with a free agent.

This is Round 1 of the Pesky Report Expansion Draft, with Derrik Maguire and Jason Stellakis squaring off as our general managers. The Utah Talons and Nashville Bandits are our two teams. Round 1 is 30 picks, with teams only being able to lose one player per round. But 15 picks per GM helps give their respective teams an identity.

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. Ma...

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. Make sure to follow us on Twitter and Instagram, @ThePeskyReport. We are officially a part of Beyond The Monster Twitter: @BeyondtheMnstr Substack: https://beyondthemonster.substack.com/ In...

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 fo...

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 Monster Twitter: @BeyondtheMnstr Substack: ht...

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...

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 a...

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 bes...

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...

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...

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 o...

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...

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 t...

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. T...