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:

• Just Asking Questions with Dave Smith, David Stockman, and Jacob Grier: Who is the lesser evil?


• Just Asking Questions with Rand Paul: Why I oppose Trump's tariffs


• Just Asking Questions with Vivek Ramaswamy: Will MAGA become libertarian, nationalist, or both?


• Just Asking Questions with Batya Ungar-Sargon: The Case for MAGA Leftism


• "What I Learned From Paleoism," by Lew Rockwell


• "Milton Friedman's Warning to DOGE," by Zach Weissmueller


• Bari Weiss's discussed tweet

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 insanit