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

Summary

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Podcast Summary: Bulwark Takes – "A Congressman Called His Penis a Pine Cone. We Have Questions."

Date: May 19, 2026
Host: The Bulwark Team (Sam Stein, Tim Miller, Will Sommer)
Episode Overview:
This episode plunges into the bizarre and headline-grabbing story of Congressman Thomas Massie, his leaked texts, and his choice to nickname his penis "the pine cone." The Bulwark trio dissects the layers of this minor political sex scandal—from the embarrassing details, to implications for MAGA-world dynamics, collateral rumors about Rep. Lauren Boebert, and a few sharp detours into Hunter Biden’s media hop and MAGA grifters. The hosts tackle the circus with their trademark irreverence, political acumen, and a heavy dash of gallows humor.

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Main Topics & Discussion Points

1. The Thomas Massie "Pine Cone" Scandal

• Background: MAGA accounts are circulating accusations about Rep. Thomas Massie’s post-bereavement sexual appetite (02:08), feeding off an interview with Cynthia West—Massie’s ex and low-level Florida political candidate.
• Leaked Details: The biggest takeaway is the surfaced texts in which Massie refers to his penis as a "pine cone," famously quipping:

  “I was going through TSA and they brushed up against the pine, or the pine cone set off like the body scanner.”—Reported by Will Sommer (03:36)

• Sexual Embarrassment as Political Currency:
  The group notes how the leak, albeit crude, is void of criminality or abuse, and spins more embarrassing than damaging—"nothing criminal, nothing like of a me too nature, Just, like, embarrassing, weird dirty talk." (03:33)
• Masculinity and Libertarian Fantasy:
  Tim Miller observes:

  “There’s sort of a libertarian fantasy to it... 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.” (05:58)

• Riffing on "Pine Cone" as Metaphor:
  Will questions,

  “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.” (04:07)
  The hosts joke about alternative objects, debate the norms of sexual bravado, and ultimately conclude “nobody sounds cool or chill in leaked sex [texts]” (05:14).

2. Fallout & MAGA World Connections

• Donald Trump Amplification:
  Trump promoting the interview brings White House-level attention to the salacious details (06:39).
• Rumored Boebert Connection:
  In the Loomer interview, Boebert’s name is introduced as a possible Massie paramour. Tim is skeptical, speculating it could be part truth or pure fantasy from the source or Massie himself:

  “I think this lady may believe that Lauren Boebert was in a sexual relationship... But I also think that Thomas Massie has a rich sexual fantasy life and...he may have just sort of been making things up.” (08:02)

• Media Context:
  The group sharply notes right-wing activist Laura Loomer’s dual role as chief rumor spreader and bigot, referencing her “deport all Muslims” stance after an unrelated attack (08:59-09:31).

3. Tangents & Bonus Riffs

Hunter Biden on Candace Owens

• Biden’s Media Motives:
  The trio reacts to the news of Hunter Biden’s planned appearance on Candace Owens. Will Sommer laments:

  “I think this sucks very badly... This is helping Candace’s clout.” (10:31; 11:51)

• Nuances of Platforming:
  The group debates the wisdom of Democrats engaging with controversial conservative figures versus outright extremists:

  “Candace is a lunatic who has advanced like tons of insane conspiracy theories... I just think is beyond the line of acceptability.” (11:25; 12:41)

McCloskey, January 6th, and Right-Wing Legal Schemes

• The Saga:
  Will covers Mark and Patricia McCloskey’s post-2020 turn as grifting January 6th 'reparation' lawyers, now locked in comic legal rivalry (13:11–14:47).
• Moral of the Story:
  “It's amazing when money gets involved.” (14:47 – Sam Stein)

Breaking Media News

• Barry Weiss at CBS News/CNN:
  Sam Stein shares a scoop on looming shifts in media leadership:

  “Paramount leadership has had informal discussions about changing Barry Weiss’s mandate at CBS News and eventually CNN in ways that would give her less control over tv.” (14:47)

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Notable Quotes & Memorable Moments

• On Sex Tapes:
  “Nobody sounds cool or chill in leaked sex [texts]... Like, no matter how cool you are, [sex texts] when taken out of context are embarrassing.”
  —Will Sommer (05:14)
• On Libertarian Masculinity:
  “There’s sort of a libertarian fantasy to it... This idea of like, my virility. The agents of the state were shocked by my, like, my manhood literally bursting out of my pants.”
  —Tim Miller (05:58)
• On MAGA Grift:
  “You can never know when the Lord's power will infuse someone and make them realize that they can get cash out of a grift.”
  —Unidentified Male (14:39)
• On Platforming Extremists:
  “Candace is a lunatic who has advanced like tons of insane conspiracy theories... I just think is beyond the line of acceptability.”
  —Will Sommer (11:25; 12:41)

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Important Timestamps

• 01:06 — Trio assembles; tease San Diego live event (“The Trio live for the first time ever, the inaugural live trio.”)
• 02:08–03:36 — Tim and Will detail Massie’s sexual escapade/‘pine cone’ texts
• 05:14 — Discussion on the universal cringe of leaked sex messages
• 05:58 — Tim Miller’s analysis of libertarian sexual mythos
• 08:02 — Boebert rumors and Loomer interview context
• 08:59–09:31 — Clarification and condemnation of Loomer’s bigotry and lack of credibility
• 10:02–11:51 — Hunter Biden’s questionable platforming of Candace Owens
• 12:44–14:47 — Will Sommer’s newsletter preview: the McCloskeys and J6 “reparations” grift
• 14:47 — Breaking news: Barry Weiss media shake-up

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Tone & Takeaways

The Bulwark team balances mockery and sharp insight, lampooning the outsized absurdity of current GOP scandals while calling out the toxicity of viral rumor-mongers and right-wing extremists. Regardless of the salacious content, the hosts remind listeners to look beyond the surface-level laughs and examine who benefits from these media circuses—and who is pulling the strings.

This episode is a brisk, irreverent run through several minor scandals and the broader theme of right-wing grift, with the classic Bulwark blend of newsroom banter, inside-baseball riffs, and meta-political analysis.

Transcript

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[Sam Stein]

Hey everyone, it's me, Sam Stein, managing editor, Bulwark, and I am with Tim

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Miller and Will Sommer.

[Sam Stein]

We're back. It's been a while, boys. How you doing? You're supposed to answer. I'm good.

[Will Sommer]

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.

[Sam Stein]

That is true.

[Tim Miller]

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

[Sam Stein]

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 we're going to go for it anyway. There's a lot going on about Tom Massie, who's got an election recording this on a Monday. He's got an election on a Tuesday.

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Not looking particularly great, but it's still up in the air.

[Sam Stein]

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?

[Tim Miller]

Well, maybe I've been monitoring this case.

[Unidentified Male Commentator (possibly a third host or guest)]

Very comfortable.

[Tim Miller]

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 life, nothing criminal, nothing like of a me too nature, Just, like, embarrassing, weird dirty talk.

[Sam Stein]

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

[Tim Miller]

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. Like, you took the pill. So I guess that's the most important takeaway.

[Will Sommer]

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. It's just not the platonic idea.

[Sam Stein]

Non fruit and vegetable.

[Will Sommer]

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 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.

[Unidentified Male Commentator (possibly a third host or guest)]

Nobody.

[Will Sommer]

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.

[Unidentified Male Commentator (possibly a third host or guest)]

Sex would have been very cringe and embarrassing.

[Will Sommer]

You know, there just, there's no way to do it that doesn't sound a little goofy when it's taken out of

[Unidentified Male Commentator (possibly a third host or guest)]

the context of the moment.

[Will Sommer]

And so I just, I want to

[Unidentified Male Commentator (possibly a third host or guest)]

offer that caveat for any additional jokes we make about Thomas Massey's pine cone.

[Sam Stein]

I don't. 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.

[Tim Miller]

Honestly, 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.

[Will Sommer]

Yeah, this is the stuff.

[Sam Stein]

An Ayn Rand legend.

[Will Sommer]

Yeah, it's almost exactly.

[Tim Miller]

Exactly. Who is Tommy?

[Unidentified Male Commentator (possibly a third host or guest)]

He's almost feminist in a way.

[Sam Stein]

Definitely shrugged at that one.

[Will Sommer]

You know, 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.

[Sam Stein]

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

[Tim Miller]

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.

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[Sam Stein]

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

[Tim Miller]

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 gives 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 a relationship with 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, you know, maybe they were. I don't know. But I also think that Thomas Massie has a rich sexual fantasy life and that the. That he may have been based on these accounts and he may have just sort of been making things up.

[Will Sommer]

A rich interior life. Men have rich interior lives, too. Sometimes people don't realize that. I think it's important to point out

[Unidentified Male Commentator (possibly a third host or guest)]

if we're going to discuss this reporting

[Will Sommer]

by Laura Loomer, that simultaneously trying to

[Unidentified Male Commentator (possibly a third host or guest)]

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, murderous attack on an Islamic center. Her response was not that we should do something to stop the attackers, but that we should ban all Muslims for the country.

[Will Sommer]

And I Do think Bear is mentioning

[Unidentified Male Commentator (possibly a third host or guest)]

that given her access to the president and her influence and her centrality to the story, how grotesque of a person

[Will Sommer]

it is that we're dealing with.

[Sam Stein]

I thought you're going to take that in a different direction. I thought you were gonna say that she has lived that. It's important to keep in mind she has no credibility whatsoever. Makes up all the time. But yes, she also is a bigoted against Muslims. So there's that too. Again, folks, just reminder, this is just

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a sampling of what you'll get in

[Sam Stein]

San Diego Hunter Biden.

[Will Sommer]

You get dick talk, you'll get righteous, righteous rants against the illiberal maga. Right. But you know, you get all of it. We're touching all the bases.

[Sam Stein]

All right, switching topics quickly. Hunter Biden's going on Candace Owens or am I hallucinating?

[Tim Miller]

Well, that's right. He's going on Candace Owens coming out later this week. I think he's kind of like a clout shark now. He's out for Internet attention. You know, he teamed up with the guy from Andrew callahan from Channel 5, a popular YouTube channel. They did a lot, a couple live shows together. I think he's just, you know, I think he's out for attention maybe. Does he have political ambitions? You know, who knows?

[Will Sommer]

I'm, I think this sucks very badly. And I express that on x.com the Everything app and several people Hunter Biden defenders replied to me.

[Unidentified Male Commentator (possibly a third host or guest)]

They're saying things such as but Tim,

[Will Sommer]

you said that Democrats should go on to Joe Rogan and but Tim, you said that it's good to engage with Hassan, Piker, et cetera, et cetera. You are the person who's saying we should engage with these things. Why is this different?

[Unidentified Male Commentator (possibly a third host or guest)]

And I would like to just address that briefly.

[Will Sommer]

Number one, Hunter Biden is not, as

[Unidentified Male Commentator (possibly a third host or guest)]

far as we know beside will suggestion, like a Democrat running for office that is trying to encourage people to support Democrats. He's a guy doing a lot of past recriminations about the treatment of his family, which is fine, totally okay to do. But I don't think that he's doing this as part of some effort to help the Democratic brand inside the Candace Owens bubble.

[Will Sommer]

But really more important than that, Candace is a lunatic who has advanced like tons of insane conspiracy theories race like unabashedly racist theories. And so like in the same way

[Unidentified Male Commentator (possibly a third host or guest)]

as I said this about going into

[Will Sommer]

those other places, it's like if you are going to do it, you're going to have to be really ready to engage and like fight with it.

[Sam Stein]

Right.

[Will Sommer]

And that doesn't really seem like his M.O. so we'll see how it turns out. We'll see how it turns out. But like, he, maybe he's clout chasing, but this is helping Candace's clout. Like, this is again, making it like Candace is once again a central, you know, node of the conversation because she's

[Unidentified Male Commentator (possibly a third host or guest)]

inserted herself into this and it seems

[Will Sommer]

like it's doing her a big favor.

[Sam Stein]

Would you felt the same way if he did Tucker?

[Will Sommer]

I would have probably felt the same way. And there'd be an interesting little caveat

[Unidentified Male Commentator (possibly a third host or guest)]

there, which is like, Tucker and him were like, friends.

[Sam Stein]

That's what I'm saying.

[Will Sommer]

There'd be some level, which I would be like, a little titillated by wondering if they went into, like, the college essay recommendation that you asked Tucker for Georgetown or something. But I think that there is a eye of the beholder on all of this. Like, if, you know, if you're going to play in the junkyard, you're going to get bit. But to me, it's like Candace, I

[Unidentified Male Commentator (possibly a third host or guest)]

just think is beyond the line of acceptability.

[Sam Stein]

Yeah, I kind of agree with you on that one. All right, last one. Will talk about your newsletter tonight. It involves kind of a maga figure from yonder. What's his name? McCluskey.

[Tim Miller]

Mark McCloskey.

[Sam Stein]

Yeah.

[Will Sommer]

And then his wife had the little mini baby gun.

[Sam Stein]

Yeah.

[Tim Miller]

She had like the Beretta and he had like the kind of AR15.

[Will Sommer]

They lived Caddy corner from my aunt.

[Unidentified Male Commentator (possibly a third host or guest)]

Big moment when that happened in the,

[Tim Miller]

in the family text chain. So. Yeah. So people may remember mark and Patricia McCloskey from the 2020 Black Lives Matter. There was a march in St. Louis, and they went by this rich lawyer's mansion, and him and his wife came out with their guns. And, and we're kind of, you know, warding, warding people off now. You know, for about a year now, he's been deeply embroiled in the quest for January 6th reparations. He teamed up with Trump's old high school classmate, a guy named Peter Tickton, who has made a career out of being like, I went to school with Trump 50 years ago. And so basically, the two of them, they, they had this quixotic quest and they thought. And McCloskey basically bails. He said, I'm sick. I don't care anymore. And then we saw last week, you know, the funds happening, 1.7 billion for four victims of the Biden DOJ weaponization. And suddenly Mark McCloskey, the next day he says, I'm healed, I'm back, guys. I can help with your cases. I can take. I can take maybe 20%, 30% again. And so. And now Peter Tickton and McCloskey are at each other's necks and they are not. And all the J6 people are like, I don't need a lawyer anymore. I'm taking this whole thing myself.

[Sam Stein]

The Lord works in mysterious ways.

[Will Sommer]

What a magical moment. I mean, if you listened to the

[Unidentified Male Commentator (possibly a third host or guest)]

Trump pastor that talked about how we

[Will Sommer]

waited 200 years for the Lord to

[Unidentified Male Commentator (possibly a third host or guest)]

give us a leader with the strength

[Will Sommer]

to bring us a ballroom, you start to think, you can never know when

[Unidentified Male Commentator (possibly a third host or guest)]

the Lord's power will infuse someone and make them realize that they can get cash out of a grift.

[Sam Stein]

It's amazing. It's amazing when money gets involved. Can I give you guys a little sort of sweetener to close this out? A little breaking news. As we're sitting here talking, Dylan Byers of Puck has a scoop. Paramount leadership has had informal discussions about changing Barry Weiss's mandate at CBS News and eventually CNN in ways that would

[Sponsor Voice (Soul Gummies)]

give her less control over tv.

[Will Sommer]

That's a shame.

[Sam Stein]

It's going so well. Tony with Tony was stuck in Taiwan. But other than that, what's tough timing,

[Will Sommer]

you know, to go to. To put a person in charge of

[Unidentified Male Commentator (possibly a third host or guest)]

news who had no experience with the news, who was an unapologetic banger of the war drums like one week before the stupidest and most disastrous war, you know, in recent memory was launched by the. By the administration did create some problems, I think, for the brand.

[Sam Stein]

Well, we'll see how it goes. She still is in a leadership role. All right, fellas, it's great to talk to you both. We'll do this again in a day.

[Will Sommer]

We'll see you in San Diego.

[Sam Stein]

Yeah. Get your tickets, folks. TheBlor.com events we're in San Diego on the 20th, then Tim and I are taking a bus going to LA 21st. If we get there in one piece, Tim doesn't kill me on the bus ride.

[Unidentified Male Commentator (possibly a third host or guest)]

Sam's a little queasy.

[Sam Stein]

I don't like bus rides. Don't like them. You might see me puke on the live stream. All right, the bulwark.com events take care of.

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