A Congressman Called His Penis a Pine Cone. We Have Questions.

Summary

Podcast Summary: The Bulwark

Episode: A Congressman Called His Penis a Pine Cone. We Have Questions.
Date: May 19, 2026
Participants: Sam Stein (Host), Tim Miller, Will Sommer

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Overview

In this lively and irreverent episode, Sam Stein, Tim Miller, and Will Sommer dive into the bizarre and headline-grabbing controversy involving Congressman Thomas Massie. The conversation centers on recent viral accounts of Massie’s intimate texts—specifically his peculiar nickname for his penis (“the pine cone”)—and the political, cultural, and simply odd implications of the allegations. The Trio unpacks the details, reflects on the impossibility of dignity in leaked sex conversations, and looks at how the MAGA ecosphere (and key figures like Donald Trump and Lauren Boebert) are amplifying and weaponizing the story.

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Key Discussion Points & Insights

1. The Thomas Massie “Pine Cone” Saga

Timestamp: 00:40–03:34

• Will Sommer provides context: A minor political figure, Cynthia West, claims to have dated Thomas Massie and describes their alleged relationship, including a supposed $5,000 offer in “cow money” (proceeds from selling cows).
• West’s claims become public via a two-and-a-half-hour interview with Laura Loomer, promoted by Donald Trump and MAGA influencers.
• Central to the bizarre revelations are leaked text messages:
  • Massie allegedly refers to his penis as his “pine cone.”
  • There's a reference to setting off a TSA scanner:
    “I was going through TSA and they brushed up against the pine, or the pine cone set off like the body scanner. And then the girlfriend says, oh, and you just took Viagra. And he says, oh you. Oh, brother. You know, so, yeah, I was Randy Rocker.” (Will Sommer, [02:35])
• The group riffs on this:
  • Tim Miller: “A lot of them [pine cones] aren’t really kind of like the ideal image for your penis. Like, if you’re trying to compare your penis to something to brag about it, I don’t know that the pine cone shape is what you’re really going for. It’s not the platonic idea in the gay community.” ([03:06])

2. The Universality and Cringe of Leaked Sex Chats

Timestamp: 03:35–04:42

• Tim and Sam reflect on how leaked sex messages never make anyone look cool, not even celebrities or historically “cool” figures:
  • Tim: “…We should be encouraging of [sex]. And nobody sounds cool or chill in leaked sex. Nobody…even Wilt Chamberlain. Sex would have been very cringe and embarrassing. There’s no way to do it that doesn’t sound a little goofy when it’s taken out of the context of the moment.”
• Sam defends Massie: “I think he comes off looking just fine, honestly…He’s like, ‘oh, my dick set off the TSA alarm.’ That sounds pretty cool, honestly.” ([04:42])

3. Libertarian Fantasies, Masculinity, and Political Subtext

Timestamp: 04:57–05:34

• Tim and Will analyze how the story taps into certain libertarian, masculine archetypes:
  • Will: “There’s sort of a libertarian fantasy…this idea of my virility, the agents of the state were shocked by my manhood literally bursting out of my pants. I mean, that is like—a guy in woods, he’s going to love that story.” ([04:57])
  • Tim: “It’s almost an Ayn Rand legend…he’s almost feminist in a way.” ([05:16])
  • Sam: Jokes that maybe Massie wants to “end the TSA because he doesn’t want to expose people to his pine cone schlong. So it’s consistent. There’s a consistency.” ([05:22])

4. Political Amplification and the Boebert Angle

Timestamp: 05:34–06:35

• Will explains how Donald Trump and the White House are amplifying the story to undermine Massie.
• Attention shifts to Lauren Boebert, who was mentioned by Cynthia West as possibly being involved with Massie:
  • Will: “Basically my theory is this. I think this lady may believe that Lauren Boebert was in a sexual relationship with Thomas Massie. He may have told her that maybe they were, I don’t know. But I also think that Thomas Massie has a rich sexual fantasy life…making things up.” ([06:01])
  • The trio alludes to the blending of reality, fantasy, and political strategy in scandals like this.

5. Media Monitors: The Laura Loomer Context

Timestamp: 06:35–06:52

• Will points out that alongside the Massie headlines, Laura Loomer also pushes extremist content, including calls for extreme anti-immigrant action, highlighting how bizarre sex scandals and fringe politics combine in the current media landscape.
  • “If we’re going to discuss this reporting by Laura Loomer, that simultaneously trying to expose Thomas Massey’s virile pinecone, she’s also pushing for the deportation of all Muslims from the country. And that was her response to a violent murder.” (Will Sommer, [06:43])

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Notable Quotes & Memorable Moments

• Will Sommer ([02:35]):
  “Thomas Massie refers to his penis as his pine cone…and said things like, ‘I was going through TSA and they brushed up against the pine, or the pine cone set off like the body scanner.’”
• Tim Miller ([03:06]):
  “A lot of them [pine cones] aren’t really kind of like the ideal image for your penis…It’s not the platonic idea in the gay community.”
• Tim Miller ([03:35]):
  “We can joke about and tease about it, but sex is good. Sex is important…nobody sounds cool or chill in leaked sex. Nobody.”
• Sam Stein ([04:42]):
  “He’s like, ‘Oh, my dick set off the TSA alarm.’ That sounds pretty cool, honestly.”
• Will Sommer ([04:57]):
  “There’s sort of a libertarian fantasy to it, right…my manhood literally bursting out of my pants. I mean, that is like—a guy in woods, he’s going to love that story.”
• Will Sommer ([06:43]):
  “If we’re going to discuss this reporting by Laura Loomer, that’s simultaneously trying to expose Thomas Massie’s virile pinecone, she’s also pushing for the deportation of all Muslims from the country.”

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Key Timestamps

• 00:40: Introduction to Thomas Massie’s scandal and Laura Loomer interview
• 02:35: Details on the “pine cone” nickname and text messages
• 03:06–03:34: Analysis of odd anatomical metaphors and social subtext
• 03:35–04:42: Discussion on how everyone looks silly in leaked sex messages
• 04:57–05:34: Libertarian and masculine readings of the TSA anecdote
• 05:34–06:35: How the MAGA world and Trump are amplifying the story; the dubious Boebert connection
• 06:35–06:52: Additional context on Laura Loomer’s broader political activity

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Tone & Atmosphere

The conversation is humorous, slightly absurd, and rich with the hosts’ signature political insight and wit. While poking fun at the salacious details, Stein, Miller, and Sommer step back to consider the more serious cultural and political undertones of how sex scandals are weaponized and how oddities in political messaging both reflect and distort the current political moment.

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For more fascinating, offbeat analysis of politics and culture, visit The Bulwark at thebulwark.com

Transcript

[A]

Hey, everyone, it's me, Sam Stein, managing editor, Bulwark, and I am with Tim Miller and Will Sommer. We're back. It's been a while, boys. How you doing? You're supposed to answer.

[B]

I'm good.

[C]

I was letting Will answer. It's the trio. Here's the thing. We're just, you know, we might be a little awkward because we're about to be together, you know, and there's a little tension building. There's, you might even say some sexual tension building as we're thinking about going through tsa, like Thomas Massie did, you know, seeing one another in San Diego. And people can still get tickets for that right now, the book.com events. We have a few tickets left for San Diego. The Trio live for the first time ever, the inaugural live trio.

[A]

That is true.

[B]

They said it wouldn't happen. They said it should be illegal, but we're going to pull it off anyway.

[A]

Outlawed in most states, but obviously not California. All right, so Tim alluded to this. We're going to give you a little teaser about what you can experience in San Diego. This may actually compel you to give up your ticket or sell it on the black market, but going to go for it anyway. There's a lot going on about Tom Massey, who's got an election recording this on a Monday. He's got an election on a Tuesday. Not looking particularly great, but it's still up in the air. But a slew of stuff happening from MAGA accounts accusing him of having a voracious sexual appetite in the time period after his wife passed, tragically. Will, can you give us the rundown, since you monitor this stuff way more aggressively than either Tim and I do, and you have more comfort talking about Viagra and men's penises.

[C]

Well, maybe.

[B]

I've been monitoring this case.

[C]

Very comfortable.

[B]

So the backstory here is that about a week ago, this woman named Cynthia west came out and she's this kind of like, very minor. She's like running for school board in some town in Florida. And she said, you know, I dated Thomas Massie. And there was this kind of like a payoff, maybe, something like, you know, this sort of weird situation where she claimed he offered her $5,000 in quote, unquote, cow money. So untraceable money Thomas Massie had made from selling cows, basically. Now, this has evolved into this week. Laura Loomer interviewed Cynthia, and it's like two and a half hours. I mean, it just came out as we're recording this. I'm just Diving in now. And it, like, gets. You know, you could hate Thomas Massie's guts. You be Donald Trump. Whatever. Trump's promoting this interview, by the way. But the amount of detail. And Massey has confirmed he dated this woman, so this is real. But the amount of detail we get on sex lives, nothing criminal, nothing like, of a me too nature, Just, like, embarrassing, weird dirty talk.

[A]

Give us the top. Give us the top three highlights so that Tim can riff off them.

[B]

Sure. So. So the most important one, I would say, is these text messages have come out that reveal allegedly that Thomas Massie refers to his penis as his pine cone and said things like, I was going through TSA and they brushed up against the pine, or the pine cone set off like the body scanner. And then the girlfriend says, oh, and you just took Viagra. And he says, oh, you. Oh, brother. You know, so, yeah, I was Randy Rocker.

[C]

Like, you took the pill.

[B]

So I guess that's the most important takeaway.

[C]

I mean, a couple thoughts here. I'm just kind of looking at various pine cones. A lot of them aren't really kind of like the ideal image for your penis. Like, if you're trying to compare your penis to something to brag about it, I don't know that the pine cone shape is what you're really going for. It's not the platonic idea in the gay community. It's just not the platonic idea.

[A]

Non fruit and vegetable guy.

[C]

Yeah. So I can't do eggplant. What would be another more appropriate one? I don't know, like a miniature baseball bat. I don't know, a mini bat. One of those souvenir bats you get at a game with the kids. I don't know. Anyway, we'll keep thinking about it, but that's takeaway number one. Takeaway number two. I just. I always do like to say this. We can joke about and tease about it, but sex is good. Sex is important. It's how we procreate the species, and we should be encouraging of it. And nobody sounds cool or chill in leaked sex. Nobody. Like, no matter how cool you are, like, whether you're like whoever the coolest person is, you have in your mind. Kendrick Lamar, Justin Bieber, whatever. You know, you go back in time, into history. Wilt Chamberlain. Wilt Chamberlain. Sex would have been very cringe and embarrassing. You know, there just. There's no way to do it that doesn't sound a little goofy when it's taken out of the context of the moment. And so I just. I want to offer that caveat for any additional jokes we make about Thomas Massey's pine cone, I don't.

[A]

I think the. I think he comes off looking just fine, honestly. I mean, relative to other sex. To your point, like, there's so much. He's like, oh, my dick set off the TSA alarm. That sounds pretty cool. Honestly.

[B]

There's sort of a. A libertarian fantasy to it, right? This idea of, like, my virility, the agents of the state were shocked by my, like, my manhood literally bursting out of my pants. I mean, that is like. Like a guy in woods. He's going to love that story.

[C]

Yeah, this is the stuff.

[A]

An Ayn Rand legend.

[C]

Yeah, it's almost exactly.

[B]

Exactly. Who is Tommy?

[C]

He's almost feminist in a way.

[A]

Definitely shrugged at that one, you know,

[C]

because Tommy Smassey wants to end the TSA because he doesn't want to expose people to his pine cone schlong. So it's consistent. There's a consistency. Oh, my God.

[A]

Has Massey talked about any of this? Has he addressed this stuff?

[B]

He has not. And you know, again, I mean, Donald Trump is promoting this. I mean, this is like, now the White House. House is fully behind this, like, two and a half hour, you know, Penthouse Forum, essentially letter.

[A]

And what about Bobert, who has been dragged into this?

[B]

Okay, I know I have my own theories about this. So here's what happened. So in this interview, this woman says it kind of. Kind of gets dragged out of her. By the way, Laura is like a very, you know, send her to Guantanamo Bay. I mean, she's. For maybe multiple reasons, but as an interrogator, because she really, like, drags it out of this lady. And so she says, you know, he was in this relationship with him, another woman, and she says, oh, who was it? She goes, it was Lauren Boebert. And so basically my theory is this. I think this lady may believe that Lauren Boebert was in a sexual relationship with Thomas Massie. He may have told her that maybe they were, I don't know. But I also think that Thomas Massie has a rich sexual fantasy life and that he may have been based on these accounts and he may have just sort of been making things up.

[C]

A rich interior life. Men have rich interior lives, too. Sometimes people don't realize that. I think it's important to point out, if we're going to discuss this reporting by Laura Loomer, that simultaneously trying to expose Thomas Massey's virile pinecone, she's also pushing for the deportation of all Muslims from the country. And that was her response to a violent murder.