Shows
Not From Boston with Bennett & HarryEp36: THERE'S BEEN A TRADEThis 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
2025-11-2543 min
Not From Boston with Bennett & HarryEp35: Jen McCaffrey ReturnsWell, 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 (@no...
2025-11-2147 min
Not From Boston with Bennett & HarryEp34: Our Chat with Chris CotilloIt’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
2025-10-2442 min
Not From Boston with Bennett & HarryEp33: Our Season Finale*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...
2025-10-051h 12
Not From Boston with Bennett & HarryEp32: WE CLINCHED!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
2025-09-271h 14
Not From Boston with Bennett & HarryEp31: Cutting It CloseThe 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 offs...
2025-09-201h 02
Not From Boston with Bennett & HarryEp30: Early Birthday GiftBennett 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
2025-09-131h 14
Not From Boston with Bennett & HarryEp29: The Piglet is Here!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
2025-08-3059 min
Not From Boston with Bennett & HarryEp28: Yankees Series, Duran Yaps, RealignmentStill 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 notfromboston.substack.com
2025-08-231h 21
Not From Boston with Bennett & HarryEp27: Boys are Back Together!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 Gi...
2025-08-151h 11
Not From Boston with Bennett & HarryEp26: Roman Stays, Red Sox Stay HotAnother 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
2025-08-091h 09
Not From Boston with Bennett & HarryEp25: The Trade Deadline SuckedWell, 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 would like to discuss this with ot...
2025-08-0357 min
Not From Boston with Bennett & HarryBONUS: Talk Dodgers to MeWe’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 other subscribers or get access to bo...
2025-08-0143 min
Not From Boston with Bennett & HarryEp24: All-Star Break Slump and Trade TalksAgain, 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
2025-07-251h 09
Not From Boston with Bennett & HarryEp23: Post-All-Star Break, Pre-Trade DeadlineThis 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
2025-07-181h 06
Not From Boston with Bennett & HarryEp22: Red Sox Heat Up AgainThis week, Bennett and Harry break down the significant sweeps of the Nationals and the Rockies, how the offense and rotation have seemingly started to click, and what all of that means as the Red Sox head into a four-game series with the Rays, followed by the All-Star Break. 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
2025-07-1152 min
Not From Boston with Bennett & HarryEp21: The Red Sox Go to WashingtonBennett and Harry breakdown the Red Sox and their consistently inconsistent performance in the run-up to their 4th of July series with the Washington Nationals.They also talk about the stupid-ass decision of visiting the President at the White House on Thursday. 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
2025-07-041h 00
Not From Boston with Bennett & HarryEp20: Out of AlignmentBennett and Harry discuss all of the new details that have emerged surrounding the Rafael Devers trade. They talk a little about what the actual team was up to this week against the Mariners, but this was another Devers/Breslow-centric 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
2025-06-201h 25
Not From Boston with Bennett & HarryEp19: This Day Started Off StrongBennett and Harry talk about the Rafael Devers trade. That’s kind of it. Happy Father’s Day 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
2025-06-1657 min
Not From Boston with Bennett & HarryEp18: The Roman Empire is HereWell, this is a LONG episode, and with good reason! The Red Sox have taken two series in a row, one against those damn Yankees, and one against the (Devil) Rays. Along the way, the Red Sox finally called Roman Anthony up to the Big Leagues, reuniting the Big Three and making Red Sox Nation happy for a change (albeit briefly).However, things aren’t all sunshine and rainbows for the boys in red stockings, and that’s what our hosts get into this week. While the Red Sox are playing more cohesive baseball, Bennett and Harry deba...
2025-06-131h 25
Not From Boston with Bennett & HarryEp17: Our MLB All-Quarter-Century TeamsOn this week’s episode, Bennett and Harry continue to dissect the problems surrounding the 2025 Red Sox season, and how utterly underwhelming it has been.On the bright side, they spend most of the episode doing what most baseball media publications have been doing lately, putting together rosters for their respective MLB All-Quarter-Century Teams! Looking back at the last 25 years of baseball, Bennett and Harry choose the best of the best to pitch and play on their fantasy teams. Check out our Instagram page @notfrombostonpod this weekend to see what we came up with. Th...
2025-06-061h 12
Not From Boston with Bennett & HarryEp16: Sorry, We Curse A Lot HereSo, this is what we get for taking a week off. The Red Sox are sinking faster than the Titanic, losing Alex Bregman to an injury, half of the lineup to a capital-S Slump, all while Alex Cora and Craig Breslow mismanage the roster. Meanwhile, Roman Anthony is tearing the cover off the ball in the minor leagues. He should’ve been promoted a million years ago.Anyway, Bennett and Harry are tired and frustrated, so in this week’s episode, they mostly kvetch about watching this awful stretch of Red Sox baseball. As the title would sugg...
2025-05-301h 29
Not From Boston with Bennett & HarryEp15: w/ Jen McCaffreyWe are so excited to bring you this episode despite the Red Sox’s recent sub—500 performance. We’re excited because this week, Not From Boston has a guest: The Athletic’s Red Sox reporter, Jen McCaffrey! After we talk with one another about the disappointing series against the Detroit Tigers, we sit down with Jen as she shares her thoughts on the current state of the Red Sox and what may happen if they continue down this path of mediocrity. Discussions ranged from the first base situation to the high probability that Alex Bregman will opt out of his cont...
2025-05-161h 09
Not From Boston with Bennett & HarryEMERGENCY POD: We Need to Talk About DeversSurprise! It’s an emergency episode of Not From Boston! Bennett and Harry sit down days after Rafael Devers publicly rejected the notion of playing at first base to discuss how the situation was handled, who was right (or wrong), and where the team goes. They also get a little carried away, talking about the recent three-game series with the Royals, and what to expect for the rest of the month. Not From Boston will be back for its regularly scheduled episode on Friday. This is a public episode. If you would like to discuss this wi...
2025-05-1258 min
Not From Boston with Bennett & HarryEp14: What Are We Doing Here?After a difficult week, the Boston Red Sox fell from 17-15 to 18-18, and then 18-19 (and now 20-19 since recording this episode). This isn’t exactly where you’d expect a playoff caliber team to be in early May. Well, Bennett and Harry feel the exact same way. Exasperated by the lack of urgency from manager Alex Cora and the Front Office, and exhausted by nine losses in one-run games, Bennett and Harry try to dissect what’s going wrong, how the team can get back on track, and they try their best to keep their cool (with limite...
2025-05-0947 min
Not From Boston with Bennett & HarryEp13: Heating UpBennett and Harry get excited this week as the Red Sox heat up. They recap the team's struggles against Seattle, as well as the team's strengths against Cleveland and Toronto. The two break down where the team has improved, particularly Rafael Devers and Ceddanne Rafaela's control of the strike zone, how good it feels to have Brayan Bello back, and how signing Alex Bregman is the gift that keeps on giving. Meanwhile, they can't ignore what's not working, from Tanner Houck's troubling pitch mix to the lack of strength at the top of the bullpen. And in Major League...
2025-05-021h 00
Not From Boston with Bennett & HarryEp12: The One Where We Lost The AudioThis week's episode of Not From Boston, unfortunately, suffers from our audio files becoming corrupted. We had to rely on the in-camera audio this week, and I promise, we don't like that either.Otherwise, the episode includes a recap of the past week, where the Red Sox roster is struggling, and where it's doing well. We talk about all things Triston Casas, bullpen woes, and we even indulge the irritating Red Sox Nation debate on whether Trevor Story and Alex Bregman will opt out of their contract at season's end. It's not like it's only April still.
2025-04-251h 16
Not From Boston with Bennett & HarryEp 11: Panic at the BallparkOn this week's episode of Not From Boston, Bennett and Harry watch the Red Sox beat the Rays 1-0. As it happens, they recap the less-than-stellar week the Red Sox have been having, breaking down the issues surrounding an anemic offense and sloppy defense. Bennett and Harry debate who, if anyone, is to blame for the team's woes, and whether or not it's time to panic, as the internet suggests.NOTE: There were some technical issues with the video recording this week. We apologize and hope to avoid similar issues in the future. This...
2025-04-1856 min
Not From Boston with Bennett & HarryEp 10: "F*ck 'Em"For the first time, Harry and Bennett are on camera together! That's right, this is the first proper video podcast episode of Not From Boston!This week, we discuss the new Netflix docuseries The Clubhouse, which followed last year's Red Sox team all season. We break down the show, which players and personalities stand out, and what we were surprised to learn! We also discuss Jarren Duran's heartbreaking struggle with mental health and his attempt on his own life. This opens the door to a longer conversation about manhood, masculinity, and what it means to keep your...
2025-04-1151 min
Not From Boston with Bennett & HarryEp 9: TORPEDO!We are officially more than a week into the baseball season, and a LOT has happened! The Red Sox, after starting the season 1-4, seemed to be getting their mojo back right before we recorded this episode. Then yesterday, they all but confirmed that, but we had already recorded this episode, so...Anyway, this week, we talked about what went right for the Red Sox, what went wrong, and what the extensions for Garrett Crochet and Kristian Campbell mean for the future of the team! Then, of course, we had to talk about the torpedo bats and...
2025-04-0458 min
Not From Boston with Bennett & HarryBONUS POD: Interview w/ Jonathan D. CohenFriday's episode went long, so here is a BONUS POD! Bennett sat down with author Jonathan D. Cohen, author of the new book Losing Big: America's Reckless Bet on Sports Gambling. Two talk about how sports gambling became so prevalent in the United States, why it can be harmful, how sports leagues are in on it, and what, if anything, can be done to fix it. Losing Big will be out today, April 1st. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit...
2025-04-0133 min
Not From Boston with Bennett & HarryEp 8: Baseball is Back, Baby!EDIT: Sorry for the delay, everyone, Bennett didn't mean to upload a podcast episode with no audio. The episode has been reuploaded, hopefully with no issue this time around.It is Opening Weekend, and as a result, we have a BIG episode for you. In fact, this episode was so jam-packed that there is going to be a BONUS POD out on April 1st! Bennett sat down to interview author Jonathan D. Cohen about his new book Losing Big: America's Reckless Bet on Sports Gambling. It's a great interview, so please keep your eyes peeled for that.
2025-03-281h 17
Not From Boston with Bennett & HarryEp 7: Considered Asking You to SubscribeOn this week's episode of Not From Boston, Bennett and Harry discuss the recent injuries to the Red Sox rotation and whether the team's depth is enough to weather the storm. Then, two break down the rumor that Masataka Yoshida will be moving to the injured list and the absurd fiction that Rafael Devers thought about maybe one day asking for a trade. And, of course, this week's episode wouldn't be complete without talking about the Big Three, particularly Roman Anthony's 434-foot home run and the 76 coffees story.In wider MLB news, Bennett and Harry discuss the...
2025-03-211h 06
Not From Boston with Bennett & HarryEp 6: BoBonIn this week's episode of Not From Boston, Bennett and Harry cover the rash of injuries and illness currently affecting the Boston Red Sox, and what the Opening Day roster might look like as a result. The two hosts also discuss the trailer for the upcoming Netflix docuseries The Clubhouse, how players balance playing the game with family life.Afterwards, Bennett and Harry break down news from around the league, including Gerrit Cole's season-ending Tommy John surgery, and the lopsided Mariners' roster. Finally, after talking about New Era's latest hat design SNAFU, the two close out the...
2025-03-141h 00
Not From Boston with Bennett & HarryEp 5: Cy Young DayThis week, Bennett and Harry cover the latest Red Sox news coming out of Spring Training, how the team is doing in exhibition games, and who may or may not be injured by Opening Day. Then, the hosts cover news from around Major League Baseball, including injuries to the New York Yankees roster, and Commissioner Rob Manfred's decision to consider maybe taking Pete Rose off the Restricted List.But first, Bennett and Harry start the show with a lengthy conversation about the arts, pursuing film and music as careers, and how artists are treated in society today.
2025-03-071h 09
Not From Boston with Bennett & HarryEp 4: Spring has Sprung!This week, Bennett and Harry catch up as Spring Training begins, and the national media discusses the Red Sox positively.Then, the two talk through the Red Sox 40-man roster, introducing listeners to each player, how they did last year, and what can be expected of them in 2025. 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
2025-02-281h 10
Not From Boston with Bennett & HarryEp 3: Who's on Third? I Don't KnowThis week, Bennett and Harry unpacked a busy week of spring training news. First, they discussed the "drama" surrounding Rafael Devers and Alex Bregman and who gets to play third. The two also discussed Vladimir Guerrero Jr. and the Blue Jays failing to agree on an extension, Mike Trout moving to right field, and the financial imbalance between Major League teams. 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
2025-02-221h 02
Not From Boston with Bennett & HarryEp 2: Full Throttle!Bennett and Harry throw away an entire episode they recorded because ALEX BREGMAN SIGNED WITH THE RED SOX!In this last-minute emergency pod, the guys break down the newest signing, how it changes the complexion of the Red Sox roster, and what this means for the season going forward. 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
2025-02-1447 min
Not From Boston with Bennett & HarryEP 1: Introducing Bennett & HarryWelcome to the first episode of Not From Boston! 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.In this episode, Bennett and Harry introduce themselves to the audience and talk a little about their background growing up together. After reminiscing about the Red Sox of years past, the two dig into the 2025...
2025-02-1255 min
Not From Boston with Bennett & HarryWhat is the Red Sox' Biggest Problem?Hi Everyone,I hope you enjoyed my interview with Dr. Palmateer last week. It was a lot of fun to put together, and I hope you found it as illuminating as I did. Today's piece covers the latest reporting about Boston's ongoing communication issue, and what can be done about it. As always, if you have any questions or comments, email them to notfrombostonsubstack@gmail.com. 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
2025-02-0406 min
Not From Boston with Bennett & HarryMy Interview with Dr. Tess PalmateerHi Everyone,As many of you know, mental health is an issue that is incredibly important to me, recently, I decided to learn more about what teams around Major League Baseball are doing in order to provide better mental health care to their players in 2025. I sat down with the mental health coordinator of the New York Mets, Dr. Tess Palmateer. We covered a lot of ground in our half hour on Zoom, and I’m excited to share our conversation with you now. This is a public episode. If you would like to di...
2025-01-3029 min