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I've watched a few chunks of the video, and I already know I'm not going to have the patience to watch the whole thing. So maybe take what I'll say with a grain of sand.

Ash says: "I can completely concede most of the reasons you don't like Trump. [...] He erratic, he doesn't seem to have well-defined principles, he's egotistical, he lashes out at people that he perceives as having insulted him. All these things are true."

So a few things. First, I think there's something deeply unsavory about listing all the ways someone is a shithead, and then going "So what? We should make him president of the most powerful country on Earth! He didn't start a war last time we did that!" Like, I don't even have a word for that. It's not a well-labelled fallacy.

But I do think it's a fallacy. Or at least, it's not emotionally honest. Ash is pretending that he can "concede" these things about Trump because they're the cost of a trade-off he accepts. I think the reality is he doesn't care and doesn't see it as a trade-off. Hence his comment on Twitter: "I like Trump as a person. I’m voting for him on policy, and because of the team he’ll have behind him. But I also like him. He’s funny, and he’s arrogant in a way I appreciate."

All that stuff about Trump being bad, but at least he's not institutionally bad like the Democrats are? Bullshit. Ash doesn't see Trump as bad. He's paying lip service to the idea that, yknow, being erratic and unprincipled and valuing loyalty over competence and lying for years about losing your election are bad traits, but he doesn't *really* see them as negatives.

Because Ash doesn't expect these traits to ever negatively affect him. The idea that Republicans are any less of an organized threat to free speech than Democrats is ridiculous when every Republican-dominated legislature has been passing laws to ban schools and libraries from having material even *mentioning* LGBT themes. Ash feels threatened by censorship of right-wing ideas, but censorship of LGBT themes doesn't seem to concern him. (Though maybe I missed the part of the video where he denounced it.)

From the outside, a lot of US politics strikes me a being like this. Democrats have a ton of terrible ideas and policies, a result of being a hydra of many semi-compatible movements. But if someone says "Republicans are better because of policy", I don't think that's honest. Republicans are equally terrible, it's just that their base doesn't especially care about the people their policies hurt.

(Also the whole comparison to Putin obviously undermines the argument. Putin hurt a lot more people than himself with his terrible decision-making.)

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> when every Republican-dominated legislature has been passing laws to ban schools and libraries from having material even *mentioning* LGBT themes

There were a TON of censorship efforts by Republicans we didn't get to discuss, the most egregious recent one was Florida threatening TV stations from running pro-choice ads: https://reason.com/2024/10/18/its-the-first-amendment-stupid-federal-judge-slams-florida-for-threatening-tv-stations/

Given the running theme of our conversation, I'll hazard a guess that Ash would nominally agree this is bad but dismiss how consequential that censorship is. Despite the amount of time we spent, I'm still unable to model Ash's objections as to why exactly some censorship is bad and some is fine (besides, you know, the obvious "Reps good, Dems bad").

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Dang Yassine, this was like watching an audit. I feel like poor Hunter was under an interrogation lamp.

I admit I’m a bit more Trump sympathetic. I don’t view him atomically and my expectation is that he will be checked by the system as he was checked in his prior term. That said, I think that antagonism with the administrative state creates better outcomes for us all.

I do think politics has broken in a lot of very fundamental ways and Trump is a symptom of that. I have some ideas how to fix it but couldn’t relate them without dropping a wall of text. Would you be at all interested in having a conversation on my substack? I think I have a system that would be right up your alley.

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I mean, a lot of very bad things can be described as “antagonism with the administrative state” so your argument is quite ambiguous. And yeah, I’m down to chat, I’ll send you a DM.

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Oct 20Edited

I don't know if there's a word or phrase for this, but I've noticed it in my work. I work with very smart people. Some of them are way smarter than me, but sometimes they are way less effective than I am. It boils down to prioritization. They're looking at a problem ("Implement XYZ") and all they see are a huge number of competing implementations, all of which have issues. They job is to pick the "best" implementation path, but these very smart people get stuck, because they elevate one particular requirement to the top and the best implementation path doesn't address that.

For Ash, assuming he's being genuine, I think he's got a bunch of competing ideas in his head about Trump and Harris, or about Republicans and Democrats, and he's given pluses and minuses to a bunch of ideas and in the wash it comes out that Trump is best. In those priority adjustments are assumptions. For democrats he's assuming the worst, and for Trump he's assuming the best. I did have the mild feeling that he might be trolling, at a few points in the conversation, but maybe it's just because I can't fathom his logic.

For me, it's abundantly clear: I compare two people, Harris and Trump, and I see a flawed candidate in Harris, who is first and foremost a politician that will say what she needs to say to get her base to vote for her (the stuff that Ash doesn't like). I see a dangerous criminal in Trump who will say anything to get elected so he can 1) stay out of jail, and 2) enrich himself and his family.

For me, the priority of how bad Trump is trumps everything else.

If someone can point to the phrase or term for this prioritization, I would appreciate it. My description of it feels really clumsy.

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I don't think misplaced prioritization is the issue here, nor would I think that's necessarily a bad thing if it was. Put another way, I can totally understand a single issue voter who cares ONLY about free speech, but I too still can't fathom the logic of someone who believes Trump is a good bulwark. I tried to explore the issue with the framework that we both cared about freedom of expression, but I have to admit I walked away wondering if that's what Ash *really* cared about or if it was just a proxy for something else.

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I'm voting for Harris, but I'm holding my nose a bit: I expect the speech environment to get worse under her Presidency.

I'm bummed we didn't hear more of _your_ case against Trump and for Harris. I'm always down to hear you grill interesting people, but it's frustrating all the same. The format is unbalanced when you spend the entire time acting as an attorney performing cross-examination, rather than offering your opinions as well. Even so, I updated a bit. You brought up a handful of bad Trump / Vance proposals that I didn't know about or had forgotten about (I think "defund the Ford Foundation for having anti-Popperian opinions" is an extremely bad idea), but overall I'd say you only landed superficial blows against Ash's position (asset seizures aside).

Above all, I agree with Ash that the various threats you guys talked about aren't the same. There are a lot of factors we should consider when evaluating a candidate's policies and actions:

- Reach: how many people will it touch? How much of their conduct will it apply to? I care much more about congressman Bob introducing sumptuary laws for all US citizens than I care about congresswoman Alice's proposals to change the dress code for Naval cadets.

- Intensity: how central is it to people's lives or the things I care about? If Alice wants to control what kind of food I can eat, I'll pay more attention than Bob's stupid laws about what I can wear.

- Effective support: you're not just voting for president, you're voting for a piece of a complicated system. Every law that passes is a small miracle. You have to line up the support and attention of a bunch of people, then thread it through the legislative process. Other types of policy implementation are different but probably just harder in a different way: you need cooperative, motivated, and competent agency personnel.

- Effective opposition: just the flip side of all that: Presidential vetos, Supreme Court skepticism, unsympathetic congressional leadership, and resentful agency personnel all thwart a policy, for better or worse.

Equation lovers might sketch out a candidate rating system along the lines of (R * I * ES) / EO; sometimes you're guessing for the values of terms and you plug in priors. For example, one thing that really shapes my thinking about this is that the courts have been very good on first amendment jurisprudence for so long that bad actors are looking for workarounds, which makes me way less worried about legislation and more worried about agencies, nonprofit groups, and media allies.

I also think you focused too much on legislation the candidates/parties proposed. If Ash had a chance to turn the tables, I would have loved to hear you address these questions (among others):

- What indications has Harris ever given that she supports free speech?

- Do any of the groups she represents care about free speech? Free speech for their enemies?

- Does she affiliate with people that recognize the importance of controversial and unpopular speech?

- Do you have any reason to believe she will try to restrain the ambitions of groups that want to limit the scope of acceptable speech?

- I agree Trump's ambitions to outlaw flag-burning are stupid and bad. But why should I care beyond keeping an eye on it? The courts are great on this and passing a constitutional amendment is really hard.

- Why should I care about Republican efforts to restrict what's available in libraries? Again, bad! But significant? Hardly any Americans are constrained by what's available via libraries in 2024, and the courts will probably fuck them up too.

There are other good reasons to vote for Harris, but promoting free speech isn't one of them, mostly because a large group of influential Democrats, supporters, and affiliated groups are in favor of restricting misinformation.

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This is a thoughtful comment that merits a longer response that I'll make in its own post. To answer a few of your questions, I think I need to make it more explicit when I have these conversations that I actively want people to put me in the hot seat. Even though it results that way in practice, it's never intended to be a one-sided interrogation.

One of the issues I have to grapple with making a judgment call about how deep into basic fundamentals we need to get into. For example, lots of people were annoyed at the Ray Epps episode because we spent an hour discussing the Deep State, but I stand by that. I had a similar approach in mind for this conversation when I ask Ash basic questions about "what is free speech and why is it good?" and I didn't know at the time but my mistake here was that I didn't explore that deep enough.

The conversation eventually unearthed fundamentally different ways we see the world and the issue of free speech, because my affirmative position would be that we live in a historically unprecedented golden age of free speech, and I wouldn't expect Kamala Harris to have an impact meaningfully different from your baseline normie politician.

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Just want to thank you, Yassine. This is amazingly thoughtful content. Thank you.

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Yassine, there's something going on with your audio that produces annoying noises fairly frequently. It's pretty obvious, so I submit this comment in case you haven't listened. ... Maybe only during the first several minutes.

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I think it's only first few minutes where I accidentally had very low mic gain, and I did best I could to repair the audio after

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Oct 20Edited

Hunter is fine with asset seizure of a non-profit because he disagrees with their methods. To me, this seems like a suppression of free speech. This really surprised me.

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That was definitely the most jaw-dropping moment for me.

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Voting for Trump because you're concerned about Free Speech seems to me like the joke Robin Williams made about Michael Jackson's chosen drug for treating his sleep problems: "taking Propofol to sleep, which is like doing chemotherapy because you're tired of shaving your head."

It's a sure case of "The cure is worse than the disease".

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I think it's ok to be a single-issue voter to the exclusion of everything else, but this assumes that Trump can be beneficial to free speech in the first place. For many reasons, I don't believe that.

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Trump is far from a free speech maximalist. He is, however, too weak, stupid and easily manipulated to be a dictator.

The man couldn't get a Team R Congress to repeal Obamacare.

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I'm curious, why didn't you post this one on the Bailey?

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For both banal and big reasons. I haven't announced it, but I'm handing off the Bailey to someone who can be a better steward. The banal reason is that I used a different audio set-up to record this and ended up with very annoying farting audio glitches in the first few minutes that are bound to be much more distracting with audio-only format, and I don't know if I have the time or patience to try to fix that.

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Hunter needs to get on Substack. I’d like to see him write a longpost on what Karl Popper said and how it’s exactly the opposite of the meme.

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The two strange Truth Social conduct rules discussed at appx. 30:00 may be an attempt to prevent Truth Social from becoming a place where the next J6-type protest is overtly planned - or at least an avenue by which the Trump team can keep an arm's length between the candidate and the wooliest fringe of his supporters. This is pure conjecture of course, but that's what struck me in the moment.

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