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PODCAST

Not From Boston with Bennett & Harry

Bennett Weinschenk & Harry Jay

Meet Bennett and Harry, two childhood friends with a couple of things in common: they"re both die-hard Red Sox fans, and neither of them are from Boston. They don"t even live in Boston now. Join these two as they talk about the Sox, reminisce about their childhood, and whatever else might come up. notfromboston.substack.com

sports baseball

All Episodes

49:27

Ep41: Welcome to the Sox, Ranger Suarez

Not From Boston with Bennett & Harry ·

2026/01/15

The Red Sox, in a panic after botching the Alex Bregman situation, have pivoted to signing starting pitcher Ranger Suarez. Does that make their rotation one of the best in the sport? For sure. Does that change how we feel about the organization and how it runs things? It does not. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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31:26

Ep40: The Red Sox Totally Blow It

Not From Boston with Bennett & Harry ·

2026/01/12

This is the one where we talk about how Alex Bregman is going to the Chicago Cubs, and how much of a mess the Red Sox organization is. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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42:30

Ep39: First Pod of 2026!

Not From Boston with Bennett & Harry ·

2026/01/07

It’s our first episode of the new year! We get right to it, discussing the moves the Red Sox are and aren’t making, how the rest of the league is shaping up, and when, oh when, will Alex Bregman sign a contract? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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23:54

Ep38: Bennett Predicted This

Not From Boston with Bennett & Harry ·

2025/12/23

If we had a nickel for every time the Red Sox and the Cardinals would make a trade this offseason, we’d have two nickels, which isn’t a lot, but it’s weird that that’s happened twice.Anyway, this week, we break down the Willson Contreras trade, what that means for the Sox, and what the heck is going to happen with Alex Bregman. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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56:47

Ep37: We're Venting

Not From Boston with Bennett & Harry ·

2025/12/14

We got together on Friday to talk about the frustratingly uneventful Winter Meetings and what the Red Sox can still do to make this ballclub better. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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43:46

Ep36: THERE'S BEEN A TRADE

Not From Boston with Bennett & Harry ·

2025/11/25

This is an emergency podcast episode! Recording this episode was literally the first thing we each did this morning. The Red Sox have traded for starter Sonny Gray from the Cardinals. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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47:09

Ep35: Jen McCaffrey Returns

Not From Boston with Bennett & Harry ·

2025/11/21

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

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42:05

Ep34: Our Chat with Chris Cotillo

Not From Boston with Bennett & Harry ·

2025/10/24

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 is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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72:50

Ep33: Our Season Finale

Not From Boston with Bennett & Harry ·

2025/10/05

*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

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74:59

Ep32: WE CLINCHED!

Not From Boston with Bennett & Harry ·

2025/09/27

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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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62:32

Ep31: Cutting It Close

Not From Boston with Bennett & Harry ·

2025/09/19

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

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74:06

Ep30: Early Birthday Gift

Not From Boston with Bennett & Harry ·

2025/09/13

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 is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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59:31

Ep29: The Piglet is Here!

Not From Boston with Bennett & Harry ·

2025/08/30

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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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81:42

Ep28: Yankees Series, Duran Yaps, Realignment

Not From Boston with Bennett & Harry ·

2025/08/22

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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit

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71:38

Ep27: Boys are Back Together!

Not From Boston with Bennett & Harry ·

2025/08/15

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

en

69:58

Ep26: Roman Stays, Red Sox Stay Hot

Not From Boston with Bennett & Harry ·

2025/08/09

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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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57:53

Ep25: The Trade Deadline Sucked

Not From Boston with Bennett & Harry ·

2025/08/03

Well, if only Bennett and Harry had recorded this Trade Deadline recap after the Red Sox had completed their sweep of the Houston Astros. Then this episode might’ve sounded a little different.In addition to criticizing the front office for their inability to *checks notes* do anything, Bennett and Harry also talk about the Sox/Dodgers series, the game Bennett got to attend, and they reassess where the playoff picture stands now that the Trade Deadline has passed. This is a public episode. If you

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43:22

BONUS: Talk Dodgers to Me

Not From Boston with Bennett & Harry ·

2025/08/01

We’re very VERY happy about our first crossover episode! That’s right, this week, Bennett will be on “Talk Dodgers to Me” to talk about the recent Red Sox/Dodgers series, the shared history between the two teams, and more!We’re incredibly thankful to Melissa, Jaclyn, and Adam for the invitation. “Talk Dodgers to Me” is a refreshing, excellent show for all baseball fans. You should definitely give them a listen if you haven’t already. This is a public episode. If you would like to discuss this with

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69:31

Ep24: All-Star Break Slump and Trade Talks

Not From Boston with Bennett & Harry ·

2025/07/25

Again, just so we’re clear: this episode was recorded just hours before Josh Naylor was traded to the Seattle Mariners instead of the Boston Red Sox. But with just under a week until the Deadline, there’s plenty of speculating to do, and boy oh boy, do Bennett and Harry speculate their butts off on this week’s episode! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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66:26

Ep23: Post-All-Star Break, Pre-Trade Deadline

Not From Boston with Bennett & Harry ·

2025/07/18

This week, Bennett and Harry talk about the All-Star Game and the Home Run Derby (and how much better they were back in our day) before getting into the weeds of Red Sox trade rumors.The two discuss where Duran might be traded to, who the Red Sox should trade for, and what else the team can do to set themselves up for success in the second half. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit notfromboston.substack.com

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