Well, we have a fun holiday surprise for you, Not From Boston fans! Yesterday, we had a chance to sit down with the Athletic’s Jen McCaffrey, which also makes her our first returning guest!

We covered a lot of ground, talking about the potential lockout, Alex Bregman, Pete Alonso, Ketel Marte (?), who gets traded for a number 2 starter, and who will still be here on Opening Day in April.

As always, be sure to like and subscribe to Not From Boston wherever you get your podcasts (including here, on Substack). Follow us on Instagram (@notfrombostonpod) and Twitter (@notfrom_boston). Check out Jen McCaffrey’s work here.

It’s the first offseason episode! Bennett and Harry kick things off right with MassLive’s Red Sox reporter, and host of the Fenway Rundown podcast, Chris Cotillo. This trio of hosts sits down for a thorough conversation about the Red Sox’s offseason, the expectations, and which free agents the team will try (and likely fail) to get.

*This episode was recorded on Friday, October 3rd, 2025*

This week, the Boston Red Sox were eliminated by the New York Yankees, ending the 2025 season. Bennett and Harry share their immediate reactions, mourning the team’s defeat. They also look briefly to 2026, and what lessons they hope the Red Sox have learned from this. Also, the Yankees suck, and they will pay for this.

As for Not From Boston, Bennett and Harry will be taking a break from the podcast this offseason. There will not be weekly episodes until probably February/March of 2026. However, there will be a few episodes coming this winter, including:

* Any Red Sox free agency/trade news

* Any major MLB news

* Interviews with Red Sox media or organization personnel

Bennett will also be writing a series of articles about the offseason on the Not From Boston Substack, so be sure to keep an eye out for those.

Thank you to everyone who listened to Not From Boston this season. You made this show possible.

The Boston Red Sox have clinched a playoff spot! Can you believe it? Bennett and Harry recorded this week’s episode during game one of the Red Sox-Tigers series, just so they could bring you their authentic feelings of jubilee.

The Red Sox may be over .500 for the first time since 2021, but it doesn’t change the fact that the vibes are…bad. After losing a series to the Athletics, the team sits in the third Wild Card spot, with the surging Cleveland Guardians only a game-and-a-half back.

This week, Bennett and Harry get into this mess, how the Red Sox have stumbled to this moment, and who might be to blame. They discuss what the Red Sox can and should do to turn this ship around before looking ahead to what will likely be another high-stakes offseason. Then, the two move on to the National League, where there is another intense Wild Card race playing out.

Bennett and Harry come to you while watching the Red Sox take on the Yankees on Apple TV+. The two catch up on the Red Sox’s struggles and injuries, and what it’ll take to stay competitive this postseason. Then they look ahead to the offseason and what troubles might lie ahead for the Sox.

Also, Bennett gives Harry an early birthday present!

This week, Bennett and Harry cover the latest stories in Red Sox Nation while watching the biggest story play out in real time! Payton Tolle, the #1 pitching prospect in the Red Sox organization, also known as “the Piglet,” made his Major League debut against Paul Skenes and the Pittsburgh Pirates last night.

Still audio only, Bennett and Harry have been busy the last few weeks, and who knows if that changes!

Still, they come together to discuss game 1 of the Red Sox/Yankees series that could make or break the season, as well as roster moves the team has (and should) make, followed by a slew of MLB news breakdowns, including on Commissioner Manfred’s proposal for league realignment.

Well, Not From Boston’s Zoom Era is over (for now)! Bennett is back in Los Angeles, which means this is the first episode in almost three months where he and Harry recorded in person!

This week, with a Sox-Astros game playing in the background, the Boys go over the last week of Red Sox baseball, how the playoff picture is shaping up, and what the Red Sox could do with their roster to increase their chances of getting there.

Then, the show takes a wild left turn, derailed by a single debate topic: Is Giancarlo Stanton a future Hall of Famer?

Another day, another belated episode. Bennett and Harry talk about how hot the Sox have been the last few weeks, whether the team can take the division from the Blue Jays, and what life will be like now that Roman Anthony is a Boston Red Sox until 2034.