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Do These Libertarians Regret Voting for Donald Trump?

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During the 2024 presidential election, a contingent of libertarians cast strategic, often reluctant votes for Donald Trump, arguing he was the lesser of two evils. Among them: Reason‘s own Liz Wolfe and J.D. Tuccille, alongside comedian and Part of the Problem host Dave Smith. Each thinks a Kamala Harris administration would have been more troubling, citing concerns about censorship, economic illiteracy, and cultural authoritarianism. More than 100 days into Trump’s second presidency it’s time to start asking: do you regret your vote?

Reason‘s Zach Weissmueller, a non-voter, moderates a conversation on Trump’s second term thus far. From the erosion of due process in immigration enforcement and the failure of the much-hyped Department of Government Efficiency initiative, to aggressive tariffs and erratic foreign policy gambits, Smith, Wolfe, and Tuccille dissect the trade-offs they anticipated versus what’s actually happened.

This episode was recorded on May 8, 2025.

Sources Referenced:
Chapters
  • 00:00 Coming up…
  • 00:42 Do you regret voting for Trump?
  • 06:00 Counterfactuals and the Kamala Harris presidency
  • 12:50 The problem with voting shaming and libertarian nuance
  • 20:30 Immigration, deportations, and rule of law concerns
  • 28:55 Is Trump undermining due process?
  • 36:50 Tariffs, economic nationalism, and free trade debate
  • 50:45 Globalization vs. protectionism: What’s hurting the middle class?
  • 59:40 The decline of affordability in America
  • 01:11:00 Reflections on DOGE, bureaucracy, and missed opportunities
  • 01:15:00 Trump’s foreign policy: Ukraine, Iran, and Israel
  • 01:20:00 Final reflections: best and worst of Trump’s second term so far

Transcript:

This is an AI-generated transcript. Check against the original before quoting.

Zach Weissmueller: Do you regret your Trump vote? Just asking questions. We’re a little over 100 days into the second Trump administration. Though it kind of feels like more as the president came in hot with an arsenal of executive orders reshaping the immigration system, the federal bureaucracy and the global economy. You might recall that Trump made an explicit appeal to libertarians to vote for him showing up at the Libertarian Party Convention tomake his pitch. Many libertarians feeling queasy about a Kamala Harris presidency and underwhelmed by the state of the Libertarian Party decided to give Trump 2.0 a try. We’ve got three of them here today, including my co-host Liz Wolf and another of my Reason colleagues J.D. Tuccille. Dave Smith, host of Part of the Problem podcast, also joins us. I think it’s fair to describe them all as reluctant Trump voters who had some serious reservations about various aspects of his agenda and maybe his character, but felt that the other options were worse. And so this seems like a good time to just reflect on how things are going so far from a libertarian perspective. Good to see all of you.

Liz Wolfe:  I see you too much.

Zach Weissmueller:  Yeah, yeah, you can just keep it to yourself. You each voted for Trump for slightly different reasons. So let’s start there. First, Dave, we had you on before the election to talk about this a little bit, which we will link to that episode. And you told us at the time that “I might be casting the most unenthusiastic vote in the history of voting.” But your reasoning was that it was purely a vote against Kamala Harris. Let’s roll the tape to see exactly why you thought she deserved to lose at the time. 

Dave Smith:(CLIP) I’ve never seen anything like the Kamala Harris campaign. There’s not even anything else you could compare it to where on every level it doesn’t exist. Like there’s nothing. She didn’t win a primary. She ran for president four years ago and didn’t make it to Iowa. She’s walked away from every single position that she was running on four years ago without explaining why. “That was five years ago. Ha ha ha ha”. That’s it. But oh, by the way, she’s the sitting vice president. Is she running on the current administration? No. And why not? Because I’m not Joe Biden. Hey, like, it’s just nothing there. And to watch her, you know, what really did it for me was this rehabilitate the Cheney’s that I just was like, what are we what are we doing here? And to me, for you know for everything the Democrats have done over the last really eight years. Um, starting with framing the sitting president for, uh, treason for these claims that he was a Russian spy, which were totally all, they produce nothing. Then they were the, um, the party of lockdowns and, uh mandates, which, okay, the Republicans were bad on too, but no question. They kind of branded themselves that then they were all in on this disastrous war in Ukraine, which has done nothing except get hundreds of thousands of people killed. And then they’re gonna essentially coup the president of the United States of America who they had spent four years pretending was not in severe mental decline and and now to run somebody who’s just nothing who’s going around campaigning with Liz Cheney is just enough for me that you deserve to lose forever. 

Zach Weissmueller:  Okay, so about 100 or so days in, and kind of imagine, I guess, the counterfactual Kamala Harris presidency. How are you feeling about things, Dave? 

 Dave Smith:  I’m, uh, I enjoy talking to you guys much more from home than a hotel room. That’s my reflection on that. Man, I hate being in hotels all the time. Uh, yeah, I mean, you know, running the counterfactual Kamala Harris, I think is a little bit difficult, um, because I don’t know, you know what, it’s hard to say exactly what her presidency would have been. Like my, uh my default assumption is that it would have I don’t think it would have just been a continuation of the Biden administration. I think it wouldn’t have been a ramp up. And I think we also talked about on that show that one of my major motivations for supporting Trump was that I thought it would really be a death blow to the corporate media and it would be kind of like the coronation. Like this had kind of already happened, but it made it official that the alternative internet world is the mainstream and that the corporate media is dead. And, and I, I got into arguments with this, but like with some people who I think are very smart, who I respect very much. Um, I remember arguing with Robby Soave.

Zach Weissmueller:  Believe it or not, that’s his real name, folks. 

Dave Smith:  Robby was basically saying, which he had a fair argument for, he was like, well, look, like the first time Donald Trump won, it actually drove the ratings up for the corporate media. And my thought was that it’s not going to work this time. And I thought so much of that was driven by the Russiagate stuff. And post Russiogate being exposed, and post the entire COVID narrative falling apart, I just think they had no more bullets left in the chamber. Like there was nothing they could say. That’s going to actually get people to want to tune in and listen. So for now, if I’m running the counterfactual, if Kamala Harris had won. In many ways, I think that would have signaled that no, actually, the corporate media still does matter more. And that even though Donald Trump, even though Joe Rogan and Theo Von and all these guys had Trump on, that didn’t move the needle as much. And so almost completely aside from the politics of it, just like on a cultural level, I think this is a lot of why so much of the woke insanity has totally receded. It’s just kind of like, oh, they lost this epic battle therefore we recognize the side that’s won. Almost every Democrat, I shouldn’t say almost, there’s a sliver of them who still want to cling to it, but almost every Democrat now recognizes that’s like, oh we can’t push this radical cultural agenda anymore, it’s gonna cost us elections. And so for that you know, and for the reasons I laid out there, I do, I, I still feel that way. Um, I think that, you know, the Donald Trump first hundred days have been, you know like a clown show in a lot of ways, there’s been some really terrible policies, um, and there’s been some good ones too. But at this point, I’m not feeling like, Oh, I regret my vote. I’d, I’d still at this point, you would say, Oh thank God we dodged the bullet of Kamala Harris. 

Zach Weissmueller:  Any reactions to that, JD or Liz, this idea that Trump was, it had to be done because there had to be a repudiation of the kind of gatekeepers that ushered us through COVID. And that is a major upside of Trump 2.0. 

J.D. Tuccille:  Yeah, I mean, there’s an element of David’s thinking of what I did. I think I described at the time my first ambiguous exploration and reason for voting for Trump, but then I openly wrote for National Post that I was voting for him, but I said I was engaged in damage control and. 

Zach Weissmueller:  I’ve got your reasoning right here, you said Trump, scumbag though he is, could be less bad than the empty vessel for the control freaks around her that is Kamala Harris. 

J.D. Tuccille:  Yeah and uh… That was my attitude then. Now is the Trump 2.0 presidency perhaps a little shittier than even I anticipated yes it is uh… I can’t say I regret it i knew it was a gamble at the time. I thought the choices we face were actually awful uh… I liked Chase Oliver as a candidate for the Libertarian Party was uh… Shambolic is still shambolic and rebuilding so I uh… By cut through the dice and said you know what at least if we disrupt what what is a and by administration Kamala Harris administration that is heavily integrated with the permanent government the civil service with the political class with the elite, if we disrupt that a little bit maybe we can at least get a different variety a less organized variety of all hold us for a little while and and break up what has been a bad experience with the Biden/Harris uh you know presidency uh nothing either of them were in control i don’t think i think the aids around works just as much the decision-making power. So, do I regret it? I don’t really regret it. I’m also not happy about my vote. It just was what it was in an effort to exercise damage, to engage in damage control in a bad situation. 

Zach Weissmueller:  Can I ask you about one other aspect of your reasoning for voting for him? You said you were kind of standing in solidarity with your wife who felt that the left’s anti-Semitism was just getting out of control. How do you feel on that front? Because there’s definitely been a pivot towards combating anti-semitism, but from a libertarian perspective, it’s kind of manifested in these. Crackdowns on speech on campus and even, you know, pulling visas and green cards from people for engaging in protest activities, what are your reflections on that particular point? 

J.D. Tuccille:  Yeah, I mean, I was and am concerned about the antisemitic turn of the Democratic Party. I’m not pleased with how the Trump administration enacts even its good ideas, but the way I look at it is that we were given a choice between a nativist, economically illiterate authoritarian political party, the Republicans, and an antisemitic, economically, you know, illiterate totalitarian political party which is the Democrats. And I’m deeply concerned about antisemitism. They’re really, my wife is an observant Jew. I mean, you know, that’s a matter of concern for me. And there are two places in the world now that are probably safe for Jews to live. And that’s the United States and Israel. You know, Jews are kind of running out of places where they can live and openly, you know, observe their faith and be visibly Jewish. Uh… Even Canada uh… Is going through a major turmoil and an open and accidentally some business tax on jewish schools and synagogues so uh… That is a major concern now is the Trump administration going about this the right way. Well I’m not gonna lose too much sleep about pulling money away from Harvard University, Columbia University depriving any of the uh… Universities of government money uh… Do I think that people ought to be busted just for writing an op-ed? No, I absolutely don’t think that’s the case, even if it’s horrendous out there. Expressing hateful ideas. But a lot of this stuff crosses that line, like what we saw at Columbia University yesterday in the library, when two security guards were driven away in ambulances after there was a quasi-riot in the library on a pro-Hamas protest. So yeah, this is definitely part of my reasoning, is that I’m troubled by the anti-Semitic turn of the progressive wing of the Democratic Party. Which is I think still dominant now, even though the Democratic Party is going through what Republicans won through say five or eight years ago, which is kind of a re-examination of what it stands for and it’s something of a breakup that may result in a coalescing new form. 

Zach Weissmueller:  Liz let me invite you both to react to anything that they said and also read you your own words back to you Remember you asked for this It’s I think you 

Liz Wolfe:  I think doing this panel just to correct the record 100% was not my idea. It was my idea while stoned. I was literally like smoking a joint on my patio and I was like, wait a second. I’m so annoyed by people on Twitter always asking me if I regret my Trump vote. What if we just got a whole bunch of Trump voters together and explored that question. So I messaged it to Zach and naturally Zach was like okay sure whatever. 

Zach Weissmueller:  Yeah, this is your chance to clear the air of weed smoke and also all the smoke on Twitter. This is, I mean, so what you said at the time was that the democracy subverting activities of January 6th disturbed me as did tariffs, but I’m more optimistic about the economic conditions that will arise as a result of a Trump administration. And I was pleased with his Supreme Court fix during his first term. Price controls, court packing, and massive amounts of government spending, which I expect to accompany a Harris presidency, will simply not work for me. So what do you, how, what’s your reflection, how do you feel about things now? 

Liz Wolfe:  I mean, I don’t really regret my vote because I don’t really spend a lot of time thinking about who I voted for. I think libertarians have historically been completely correct in basically saying your vote doesn’t matter to the degree that you think. You are probably best served sitting at home. It’s just really not going to turn the outcome of an election. And the fact that people spend so much time sort of shaming people over this type of thing is really, it’s just such a waste of breath and energy. That said… I always saw Trump, and I think I could have articulated this better at the time, I always saw Trump as a very high upside, very high downside candidate. And I think the thing that’s been really frustrating for me is that so far we’ve seen pretty much all downside. In the early days, I was feeling really optimistic about what DOGE could do. And I recall reading the news about the CFPB being dismantled and like sending that link to a few of my friends and just feeling like, wow, I’ve been so vindicated. This is awesome. And DOGE seems like the only sort of hope of actually meaningfully reducing the size of government, at least in my lifetime that we’ve seen, like, this is incredible. And it’s just absolutely wild how that really has not come to fruition. I think as it was initially conceived of by Vivek Ramaswamy and Elon Musk, I think it could have been successful in that form when Vivek was sort of kicked off of the project and it became an Elon Musk initiative entirely. Um, it somehow just became, you know, profoundly unsuccessful. And I think a lot of their sloppiness and accounting has really kind of discredited some of the limited government cause, which makes me concerned from like a 4D chess political perspective, like does this sabotage government slashing efforts for like a decade to come, I hope not, but it’s possible and then in a bunch of other areas too, it’s just been. Absolutely horrible, you know, trying to make sense of what his tariff policy actually is and why. And what he wants those final amounts to be. I mean, the announcing of reciprocal tariffs has been such a problem. I’m concerned about that as well as the sort of constant 90 day pauses. And then immigration policy, you look at the degree to which he’s just really aggressive with deportations. And look, there’s some amount of like, deportation was never going to be, soft and cuddly and fuzzy, right? Like it was never gonna be sealing the border again and rolling back some of the Biden era chaos. Was never going to be something that looked good. But the way that the Trump administration has done it has been just shockingly, appallingly bad. And I really do think that there’s like such an erosion of due process, which leaves me feeling like, how do we possibly get people to care about this again? The number of fellow Americans who I’ve seen justifying that type of behavior by the Trump administration is really, really frustrating to me, especially because using that alien enemies act to attempt to deport these people. Keeps getting swatted down by various judges. We saw the Fourth Circuit especially issue a really scathing rebuke. And I’m just a little bit like, you know, like even Trump appointed judges don’t agree that the Alien Enemies Act can be used in this way. And I think that’s a really big problem. I think the mechanism by which we do this really does matter. 

 Dave Smith:  On that topic, yeah, go ahead, please do. No, there was something, what Liz said up top there, I feel like I just wanted to like stress because there is something that I’ve, it’s very interesting the way a lot of libertarians do react to voting at all. And it’s almost as if in some weird way. They buy into the same principle that statists do. And like, I remember there was this one, one time, many years ago, I was on a Fox news show. I was on Kennedy, uh, and Julie Roginsky, who’s like a Democratic strategist. She, at one point, like I forget what it was, but it was like, I criticized Hillary Clinton, and then she was like oh, so you must love Donald Trump, you know, the typical thing libertarians are used to getting, and I was like no, I actually don’t like him either. And she was, like, wait, so who did you vote for? And I was, I didn’t vote. And she goes, this is all on air, and she goes well, if you don’t vote, then you can’t complain. And I’m like, really? Because I’m about to. So like that’s, it’s like, that’s like an, it is an empirical claim, and I’m about to demonstrate that that’s not true. And every libertarian recognizes immediately like how ridiculous that is but then they almost apply the inverse when they find out like you’re voting for one of the major party candidates like oh well now you’re responsible for all of the bad and it’s like all of this is so ridiculous it’s like look from libertarian first principles you can deduce that like we’re under duress. We are forced into we’re forced into a false binary where that shouldn’t exist. But one of these two people is gonna be president and it’s completely reasonable for libertarians to say I find one of them to be slightly preferable to the other one. So I’m gonna throw a vote their way and see what ends up coming of all of that. So that was kind of just my I just I found it very interesting watching like how people how libertarians implicitly like conceptualize what voting is as if this means it’s like a full endorsement of everything that this person has ever done or said or whatever they will do in the future rather than what it really is which is essentially a strategic guess you’re kind of going like 

Liz Wolfe:  This is the thing that’s like wrinkled me so much in the aftermath of my scandalous Trump vote, which has been the number of people who respond to me constantly on Twitter or YouTube or whatever and say, you voted for this whenever I’m criticizing a Trump policy. And it’s like, yes, I voted for this candidate extremely reluctantly, but I didn’t endorse every single thing that you would end up doing. And wouldn’t you, in fact, rather have people who will vote for a candidate and still retain their independence and their ability to you know, critically assess each specific policy that this president puts forth and then is able to call balls and strikes and say, this policy is good, this policy’s not aligned with my values. Like, it’s confusing to me, and especially for a journalist to do that, like it’s confusing to me what they want. Do they want me to vote for Trump and then become like a MAGA-tard Trump sycophant and just, you know be super, super excited about every single thing his administration does? Like, would they feel better served by me doing that? I wouldn’t feel good. By me doing that. I feel much better about saying, look, I made an educated guess. So far, I don’t really like how the guess is working out. It’s not really aligned with my values and beliefs. As a libertarian, I consistently feel like there’s no good option available to me. And you know what? The only thing I can do as a journalist for the next four years is try to be honest about what is good, what is bad, and what I know and what I don t know about what Trump’s doing. 

J.D. Tuccille:  Yeah, I’m gonna get down on that. Yeah, go ahead. I was just gonna say, I mean, I am just amazed. I’ve known people for decades who will come at me with, and it’s clear that they kind of live at the intersection of tribalism and retardation, because it’s a matter of being, they insist that you be all in. You’re either entirely on Team Red or entirely on Team Blue, and they can’t, and they’re angry with me. They’re furious because I write some columns that say, yeah, I think DOGE is a good idea. I’m going to scare the Department of Education. And then I write a piece saying, no, Trump’s way over the top with executive actions and his trade policy is insane. So yeah, tribalism, the insistence that political identity is all, is a be all and end all. And actually, this is a good way to riff and say this. I’ve recently seen two studies, one from 2017 from Stanford, another from Political Psychology published recently. Both said that now political identity overshadows race and ethnicity as a matter of personal identification. And a source of interpersonal animus in this country. So yeah, people live in this kind of intersection of, and I’ll say it again, of retardation and tribalism. And they insist that you go all in on this identity instead of saying, you know, the vote worked out or the vote didn’t work out, and I think I’ll just be critical of the policy, the action, the politician rather than the candidate. 

Zach Weissmueller

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