Why Does This Keep Happening to Republicans?

Summary

Podcast Summary: The Bulwark – "Why Does This Keep Happening to Republicans?"

Date: May 23, 2026
Main Speakers: Sarah Longwell (A), Tim Miller (B), Will Sommer (C), Sam Stein (D)
Theme: An irreverent, biting discussion on the Republican Party’s repeated cycles of chaos, the January 6th settlement fund controversy, right-wing grift, and the strange media alliances between conservative figures and Hunter Biden.

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Episode Overview

This episode brings together The Bulwark’s "trio" — Tim Miller, Sarah Longwell, and special guest Will Sommer — for a live, unscripted, and frequently hilarious conversation. The mains topics include the fallout and infighting over the massive January 6th settlement fund, the ecosystem of grifters and lawyers jockeying for a cut, and the odd spectacle of Hunter Biden appearing on Candace Owens' podcast. Throughout, the hosts maintain a sardonic and critical tone, exposing the self-serving opportunism and absurdities on the American right while highlighting the political and cultural stakes.

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Key Discussion Points

1. January 6th Settlement Fund—Chaos, Grift, and Infighting

Timestamps: 01:45–08:41

• Background:
  The hosts jump into the recent establishment of a $1.776 billion settlement fund intended for January 6th defendants and related figures. Will Sommer, described as the expert on right-wing internet subcultures, provides insight into the wild scenes playing out as the "J6 community" scrambles to claim their share.

• "Lectern Guy" and the Outlandish Claims:

  • Several J6 defendants are demanding huge sums (the "lectern guy" wants more money due to his notoriety; Mike Lindell asks for $400 million—[02:24], [02:44]).
  • "We're starting to see more. Mike Lindell says he wants 400 million. 400, which, okay, I guess we'll give you a fourth of the fund. You know, it's crazy." — Will Sommer, [02:44]

• Failed Attempts at a "January 6th Home":

  • Sommer recounts a failed effort by the J6 crowd to takeover a senior home in Virginia and create either a "group house" or "content house" for themselves ([03:06]–[03:54]):
    • “I was watching the videos, these January 6th guys, like wandering dimly lit halls. It was like the back rooms.” — Will Sommer, [03:37]

• Second-Tier Grifts: The Legal Sharks

  • Sommer details how lawyers like Peter Tickton (whose only claim to fame is attending high school with Trump) and Mark McCloskey (of St. Louis fame) are positioning themselves as champions of J6 figures:
    • McCloskey bows out due to "illness," then reappears after the fund is announced.
    • Sommer quotes Tickton's darkly comic line: "I didn't know there was a cancer you could heal if you think you have a chance to get some money." ([04:39]–[05:50])

• Will the Money Actually Be Paid Out?

  • The group debates the obstacles—Senate interventions, Trump-appointed claims board, the technicalities of filing claims ([06:22]–[07:10]).
  • Tim and Sarah vent about the injustice:
    • “They're stealing your money, and they're giving it to fucking insurrectionists. It's… white MAGA reparations, and it's fucking outrageous.” — Tim Miller, [07:33]
    • Tim wonders if letting these outrageous payouts proceed could backfire on MAGA, illustrating the cost of their movement to ordinary supporters ([07:54]–[08:36]).

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2. Hunter Biden’s Bizarre Media Moves: Candace Owens Partnership

Timestamps: 08:41–13:21

• Setting the Scene:
  Tim reveals that Candace Owens' newest podcast guest is none other than Hunter Biden—a partnership that defies easy explanation ([08:41]–[09:05]).

• Hunter’s Defense and Clout-Chasing:

  • In the brief clip, Hunter rails against the “DC elite,” claims his dad was "never part of the Epstein class," and offers up conspiratorial references about Gaza and Iran ([09:37]).
  • "Hunter Biden…he loves the infamy. He’s kind of like a clout shark, what you might call him." — Will Sommer, [10:37]

• Hosts’ Takes on the Hunter–Candace Dynamic:

  • Will Sommer finds the shift — from Hunter’s progressive podcast appearances to the far-right Candace Owens — “very strange” and “frustrating” ([11:05]).
  • Tim Miller provocatively suggests, “I think Hunter should do more media. I think he comes across sympathetic.” — Tim, [11:12]
  • Sarah adds a character reading: “Here’s the thing about Hunter: all the hookers say that he was super nice… He’s got great hooker reviews.” ([11:32]–[11:49])
    • This leads to a tongue-in-cheek debate about whether Hunter is acting in good faith and if there’s value in Democrats appearing on right-wing platforms ([12:20]–[13:05]).
    • "Seems like he's shitting on the Democrats on Candace Owens platform." — Tim Miller [12:46]
    • "He should probably just parent his child." — Tim Miller [13:04]

• Candace Owens' Motivation:

  • Will Sommer: "I mean, I think she gets attention. Yeah, I mean, she loves attention, like, of any kind. And, you know, it puts her at the center of things is all." ([13:21])

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Notable Quotes & Memorable Moments

• Will Sommer on January 6th grifter culture:

  • "These are some great characters… Peter Tickton. Now his claim to fame is that he went to high school with Donald Trump. That’s it." — [04:19]

• Absurdity of the "content house":

  • "A hype house where they would just cut videos with each other. January 6th content." — Will Sommer, [03:54]

• On the outrageous payouts:

  • "There’s a simplicity to that story that I like… you got to do your laundry, and they’re fucking taking your money and they’re giving it to these assholes. They stole it from you." — Tim Miller, [07:54–08:36]

• Hunter Biden’s strange allure:

  • “He’s kind of like a clout shark… But I don’t understand why he went from this kind of, like, lefty podcast guy… to, like, the next step was Candace Owens.” — Will Sommer, [10:37]

• Dark Humorous Aside:

  • “Sprinkle a little Ebola on top, maybe… a hint of okay… Hey, just a touch, a little pinch.” — Tim Miller and Sarah Longwell, in riff about MAGA and self-harm, [08:36–08:41]

• On Democratic engagement versus self-sabotage:

  • “Sometimes… you say that Democrats should go engage on these platforms, and it’s like, it doesn’t seem like Hunter’s engaging on that in service of trying to bring people into the Democratic fold.” — Tim Miller, [12:40]

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Key Timestamps

• 01:45 — Introduction to Will Sommer and background on right-wing internet culture
• 02:24 — Stories from the January 6th community, bizarre claimant demands
• 03:06 — “Content House” and failed community compound in Virginia
• 04:19 — The lawyers’ grift and their manufactured credibility
• 06:22 — Will the settlement fund actually pay out?
• 07:33 — Tim's rant on injustice and the political stakes
• 08:41 — Hunter Biden on Candace Owens: context and reactions
• 10:37 — Will’s breakdown of Hunter’s media motives
• 12:40 — The difference between legitimate engagement and opportunistic self-sabotage

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Tone & Language

The conversation is energetic, profane, and deeply skeptical of both MAGA grifters and the spectacle of Hunter Biden’s moves. Sarcasm, dark humor, and exasperation pervade the analysis, with rapid-fire banter and punchlines. The hosts keep things entertaining while refusing to paper over the real dangers and cynicism on display.

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Conclusion

"Why Does This Keep Happening to Republicans?" delivers an irreverent, insightful peek into the ongoing cycle of right-wing dysfunction and opportunism. The chaotic scramble for “reparations” among January 6th figures provides dark comedy and a window into grift culture, while Hunter Biden’s foray into MAGA-friendly media shows how bizarre and transactional modern political culture has become. The Bulwark team balance outrage, gallows humor, and a flash of hope that public exposure might, one day, yield accountability.

Transcript

[A]

Do the people want the trio? The people want the trio.

[B]

Fine.

[A]

I guess I'll just leave then. You'll be back.

[B]

All right, sir.

[A]

I'll be right back. We're gonna do the trio, guys. Welcome to the stage. Will Summer.

[B]

Hello.

[A]

I'm not hosting anymore. Thank God. Get me another whiskey. Same mic. All right, Keep the mic. Hey, Will Summer.

[B]

Hey.

[C]

Hey, everybody.

[B]

I felt like that wasn't a sufficient welcome for Will Summer. Oh, no.

[C]

It's so nice.

[A]

Thank.

[B]

Just before we get to the trio, to let you know the two debate topics we skipped, Tim idiotically, was going to argue that there was a Tom Massey Lane in 2028.

[A]

I think that there is.

[B]

And Sarah wanted to debate me on whether the. The blood alcohol content level was too high.

[A]

Not. Not your personal. Not whether your personal blood. Get off the stage. Whether your personal blood alcohol when you drive.

[B]

Sorry.

[A]

Yeah. All right, Sarah. We let Sarah off the hook. You all were cheering for. Why don't we cut the part where you're gonna defend drunk driving? We'll just keep everybody on your good side. Saving Sarah from her side, and she's like, no, no.

[B]

Baiting her to come back on. All right, this is the Trio. So let's start with the. January 6th.

[A]

We did a song.

[B]

Yeah, we should.

[C]

I was thinking the Trio.

[B]

Can we just do the Tim podcast song? No, no, no, I'm on it.

[A]

We're gonna get a song.

[B]

We should get. If you don't know.

[A]

Will. Will.

[C]

Thank you. I love San Diego. Thank you.

[B]

Will lives in a weird part of the world. He's been bred, and he's had his professional career built around right wing Internet culture. And I would argue, honestly, that you're the foremost authority on this odd universe, which, frankly, is now a power center in our politics. And this week, the biggest story, I think, in your Universe has this January 6th Trump settlement slush fund of 1.77. $1.776 billion. So are you profund?

[A]

No, I'm not.

[C]

You know, we do have to remember. I mean, these people did January 6th.

[D]

Right?

[C]

Like, that is crazy. I mean, we get so lost in it. Right before I came up here, the lectern guy. Remember the guy who stole the lectern? He's like, well, I should get more money because I was kind of infamous and, you know, people were really mad at me. And so, you know, we're starting to see more. Mike Lindell says he wants 400 million. 400, which, okay, I guess we'll give you a fourth of the fund. You know, it's crazy.

[B]

So what is going on in the January six community right now? Like, I'm talking about the rioters who probably are still in touch with each other, maybe, you know, have some sort of discord channel or something like that where, you know, they all kind of want to get a piece of the pie. We saw the CNN clip, for instance. This one obscure guy wanted $30 million. Lindell wants $400 million. Are they starting to turn on each other?

[A]

Oh, my God.

[C]

Well, I thought you were going to say they have a lot of discord. Right. Which they certainly do. There was a point where they tried to take over this old senior citizens home and they were going to make it into a compound in Virginia there and it all fell apart. Obviously. They're always like scheming and. Yeah, they're really mad. Everyone.

[A]

Now tell me a little more about that.

[C]

Yeah, I looked into it. I mean, it was this old giant senior citizens complex and they took it over and they were like, this is going to be a home for January 6th. People wouldn't be like that in your neighborhood.

[A]

Right.

[C]

And I mean it.

[A]

Where? In what state?

[C]

I think in Virginia.

[A]

Florida. No, Virginia. Yeah.

[C]

And they.

[B]

But.

[C]

But there was. Obviously it was a spooky place. I mean, it was kind of. I was watching the videos, these January 6th guys, like wandering dimly lit halls. It was like the back rooms. Right. They talk about that.

[B]

But why? Why did they want to do that?

[C]

Because they need a place to live. All the January six people.

[A]

A group home.

[C]

A content house. Yeah, a content. Yeah, a hype house where they would

[B]

just cut videos with each other.

[C]

January 6th content. I mean, they did. Yeah, it was a. I don't. I should have written, but.

[B]

Sounds like a good false flag. Is there talk a little bit about the newsletter you wrote about the lawyers? Because, yes, this is also sort of a second tier grift here happening, which is the lawyers also want their 30% cut of these settlements.

[C]

Yeah, these are some great characters. Right. So we've got this guy named Peter Tickton. Now his claim to fame is that he went to high school with Donald Trump. That's it. Right. And he wrote a book. Oh, he was such a great guy in high school. Whatever. And in fact, he's seen him, Pierre's lawyer. Speaking of. And so him, he teamed up with a guy named Mark McCloskey. Now you may remember Mark McCloskey from

[A]

20 20. Who remembers Mark McCloskey? Yeah.

[C]

Okay, sickos, big Mark McCloskey crowd here. Okay? But basically, you know, he stood in front of his house in St. Louis during a Black Lives Matter march with the guns. Mark, Mark. Mark and Patricia McCloskey. And so now he, he teamed up with Peter Tickton and they said, we're going to represent all the J6 people and we're going to get him reparations. And this went on for a year that obviously it didn't look like it was going to happen in April, he says, Mark McCloskey says, Guys, I'm sick. I just got to bow out. It was sort of like he was like, this isn't going anywhere, right? And then a day after the fund gets announced, he goes, I'm healed, I'm back and I'll be your lawyer again. And, and Peter Tickton, he's like, praise the Lord. And so he's seeing the righteous gemstones shit. He said, he did say he was like, like with God on our side, nothing will. So Peter Tickton, he was like looking at his yacht or whatever, all. Everything he's going to buy with this money. And he says, he told me, he said, I didn't know there was a cancer you could heal if you think you have a chance to get some money. And I was like, wow, these guys hate each other. Which is something, I honestly think a lot on this beat.

[B]

What do you make of. What do you think is going to happen with this? Fun, Tim? Like, is it actually going to be doled out?

[A]

How often are you talking to Pete?

[C]

This was a first timer, honestly, I got him on the phone and he was just like, let me tell you how much I hate this guy.

[A]

Interesting. Interesting. That's nice. I'm kind of jealous of you sometimes. You just get to meet so many interesting characters, you know? I have to talk to Tom Nichols again. Same old, same old. Are they gonna get their fucking money? Yeah, I think so.

[B]

I don't know.

[C]

It feels like the Senate's gonna try to intervene, but I don't know if they can. I mean, we saw some took the money out.

[B]

Well, they gotta. They actually have to file. Who knows what they're gonna do. Technically they have to file a claim in this Trump appointed board. Whatever this is is gonna adjudicate it, I think. What did Todd Blanche say about it? Oh, they're asking Todd Blanche tonight. I think he's on scene and they're like, are you really going to give it to people who like beat up cops on January 6th? And he's like, what do you say? He's like, a lot of people have gotten money who've beat up cops.

[C]

Yeah, he said a lot of people have beaten up cops and gotten money. Really?

[A]

Is that true? I don't.

[B]

I mean, I think he meant police, like, legit police brutality claims and people.

[A]

Those are people that got going.

[B]

I think he meant they fought back. I don't know. It doesn't make any sense. So I get. My theory is that they have to rush. They're gonna rush it out before any.

[A]

I don't know. But he wants it for the bribes, like, he wants it for the. For the blackmail. Yeah, they're gonna have to keep it. They're gonna have to keep it. I don't know. I'm of two minds about it. We talked about this a little bit downstairs, and, you know, like, on yesterday's pod, we were raging, and I'm very upset. The whole thing is fucking insane. I mean, like, they're stealing our. They're stealing our money. Like, they're stealing your money, and they're giving it to fucking insurrectionists. It's, you know, white MAGA reparations, and it's. It's fucking outrageous. And so at one level, I'm like, I don't want them to take our fucking money because fuck you. There's the other part of me that's like. It's so outrageous, though, that. Let him do it. No. Well, do we want to stop them from themselves? Isn't this part of the stove touching? Like. Isn't it part of the stove touching, like there's a. I guess the dark angel inside of me, the dark wolf is like, I kind of want gas to be $7 a gallon, and I kind want people to feel MAGA. People to feel pain and then to be reminded, you know what? Actually, you were going to work all day. Like, you're going to autozone and, you know, working your ass off, and you came home and you're sweaty and you got a fucking parent. You got to do your laundry, and they're fucking taking your money and they're giving it to these assholes. They stole it from you. And there's a simplicity to that story that I like. That's all.

[B]

Sprinkle a little Ebola on top, maybe

[A]

a hint of okay.

[B]

Hey, just a touch, a little pinch. You talked about dark characters. A real duo has teamed up for reasons I'm not totally sure. Candace Owens heard the newest.

[C]

It's Will's girl.

[B]

The newest guest on her podcast is Hunter Biden.

[C]

There shot.

[B]

I guess they're not watching. They're not as into the Internet culture as you.

[A]

Will.

[B]

Let's play A little clip, and I have questions afterwards. Let's play the Candace Hunter clip.

[A]

What's your. What's your opinion on Kamala, then?

[C]

It's a big event.

[B]

Is that it? That's the full clip.

[A]

All right, fine. There's more. There's more to it. Politics is corrupt.

[D]

But something's changed in this. It's not left or right. The DC Elite of the. Of the left, they crushed my dad because he was never part of that club. He was never part of the Epstein class. You know, one thing he didn't do, he didn't greenlight to turn Gaza into a Trump golf course with the maitre d being Jared Kushner. War in Iran that they started, that every president before him was pressured by the Israelis.

[C]

I do think there was something about

[A]

the Charlie Kirk assassination that everyone just sort of looked up.

[D]

They're the people that Charlie Kirk made. The level of disloyalty or fear. I don't know what it is. And the criticism of you for asking the questions for someone who was like a brother to you, it's like, what the f. Were you talking about? I listened to you, and I go, right on.

[C]

It's crazy.

[B]

Oh, come on. You're entertained, Will.

[A]

I am not entertained.

[B]

Will, just contextually, how crazy is this partnership here?

[C]

This is. It's pretty crazy, right? But I think also, like, Hunter Biden, I think, has kind of shown himself to be, like, he loves the infamy. He loves, like, the. He's kind of like a clout shark, what you might call him. Like, he teamed up with this other podcast guy, and they did some shows together. But I don't understand why he went from this kind of, like, lefty podcast guy at Channel 5 News or whatever to, like, the next step was Candace Owens. And, you know, I. It's very strange. And also, it's just, like, frustrating because it's like, do we really need to relitigate, like, the Biden administration? I mean, I guess that's how he feels.

[B]

I have a hot take on this. I think Hunter should do more media.

[A]

Oh, my God.

[B]

I think he comes across sympathetic.

[A]

Hunter Biden.

[B]

Hunter Biden. There is a part in there where she starts asking him about the laptop and his crackers, and he's like, yeah, I did crack. And I'm like, okay, I get it. Yeah, he did it. Yeah.

[A]

Here's the thing about Hunter. All the hookers say that he was super nice.

[B]

Yeah, they do. Legit. They do.

[A]

Like, he's got great hooker reviews. And there's something to be said for that, you know, because my understanding. Not my cup of tea.

[B]

Why, are your hooker reviews not good or something?

[A]

No, no, not a problem there, Sam. But my understanding is that sometimes there can be, you know, some violence and, you know, men can be dicks to hookers, you know, maybe shortchange them, et cetera. And so that Hunter, you know, and if I were to be somebody that was using crack, Ike seems like somebody that you'd have. We'd have a good time, I think. I think we'd have a nice time. I think we'd have a good time in Fort Lauderdale together. I didn't love it when he was trying to be the shadow president of the United States in 2024, though. And I don't really think that he should be telling Candace Owens, like, hey, kudos to you for your questions about the Charlie Kirk assassination. Like, you're really out there and I appreciate it. And I don't really think that he should be like, the Epstein class came from my dad. I don't think any of that is helpful. Sometimes I can already hear some people being like, but, Tim, you say that Democrats should go engage on these platforms, and it's like, it doesn't seem like Hunter's engaging on that in service of trying to bring people into the Democratic folds. Seems like he's shitting on the Democrats on Candace Owens platform. And, you know, I think he should probably just parent his child.

[B]

All right, and what is. What is, Kent? I mean, fair point. I slipped that in at the end. But he can't argue that. What is.

[A]

He did sue to parent his own child.

[B]

He should probably parent his own child.

[A]

Not great. Probably do that.

[B]

What does Candace get out of this?

[C]

I mean, I think she gets attention. Yeah, I mean, she gets attention. I mean, she loves attention, like, of any kind. And, you know, it puts her at the center of things is all.