On his Substack, The Cholla Express, Billy Robb recently mused about the way President Donald Trump and increasingly, his loyalists, use humor in official White House communication.
The result, Robb writes, is confounding for opponents of the President’s agenda, because it’s hard to figure out when — or if — he’s being serious.
Robb joined The Show to talk about why he’s concerned about this, not just as a political observer, but also because of his day job.
Full conversation
BILLY ROBB: I'm a civics teacher by trade, and I take the constitutional order very seriously and just been observing, I mean, for a long time, but especially the last few months, the sort of trollish nature of the Trump administration and the way they wage politics, and, and how it's kind of become people posting things like Trump 2028 and, you know, posting memes of Trump dressed like a king and supposed to be joking I think?
SAM DINGMAN: Because, yeah, well, I mean that's one of the interesting spaces that I think you're exploring here in this essay is, as you put it in the in the newsletter, you're supposed to be in on the joke unless maybe it's serious, in which case I'm not sure, and neither are Trump's loyalists, as you, as you write.
ROBB: Yeah, I don't, I don't think some of them do and I, that part stood out when about the Canada thing, right? Because after we got elected, he started talking about, you know, annexing Canada, why it should be the 51st state, and his own spokesperson has asked about it at a press conference and, and says, yes, Canada should be the 51st state, but she's kind of smiling.
DINGMAN: And so this is Karoline Leavitt, the press secretary.
ROBB: Yes, and so it's just, it's just very disconcerting and very, both tiresome and worrying to me that this is all a big joke, especially because Canada is not in on the joke. You know, the people of Canada and the politicians of Canada are taking it very seriously.
DINGMAN: Well, this is the thing that I think you're, you're hitting on here that feels like such an urgent question of this moment is who is in on the joke? And one of the things that you also point out in your piece that I thought was very interesting is it's not like humor is a new political tool, and you even cite people like Barry Goldwater. Tell us a little bit about why you feel like the way Barry Goldwater used humor is different than the way Trump and his emissaries do.
ROBB: Well, well, yes, like I'm, I'm not trying to be a buzzkill, and I think humor is, you know, brings life to you know, social groups, and it's, it's, it's been used very often in, in politics, whether it's satire, you know, whether it's, you know, telling jokes to relate to the audience.
And a lot of Republicans have been excellent at that from from Ronald Reagan and Goldwater back to, to Abram Abraham Lincoln, but I see with Trump t's a completely different thing in the sense of, and it probably has to do with, who he was before he became a politician, which was, you know, a reality TV show host and sort of an expert at getting attention.
DINGMAN: Well, yeah, I mean, I think you're, you're, you're bringing up something really critical there, Billy, which is in the example in your piece that you cite of Barry Goldwater, you're talking about how in in the New York Times in 1964, he's, I guess, campaigning in Minnesota, and, you know, he's trying to make a connection with, with the locals and he says like, “Wow, you know, you guys got a lot of nice lakes here,” and then he says, “Where I come from, we have so little water that the trees chase the dogs,” which is, you know, it's a great line, but when Goldwater is doing that he's using humor as in a way to sort of express humility, like he's sort of poking fun at himself by way of poking fun at the the part of the country that he's from. And when Trump uses humor in your framing, he's doing it really to build himself up.
ROBB: Right. And when, I mean that joke, anyone can laugh at it, right? If you're a MAGA Republican listening to this, if you're a Democrat, progressive, you can laugh at that joke, and he wasn't using a humor to alienate people or to divide people.
I think that's another element of the trolling aspects of the MAGA coalition is that, you know, it can be bullying, it can be very divisive, and I think that's like psychologically difficult because trolling works, right?
DINGMAN: Yeah. Well, so Billy, that makes me think about kind of the motivations behind the form of joking that we've been talking about. When Goldwater makes the kind of joke that he made, it's at his own expense and something you hear often from professional comedians is that they're like, well, I make fun of myself because I'm worried you will, so if I'm doing it, then you can't.
But the type of humor that you're talking about Trump and the Republicans more broadly deploying these days, it's not at Trump's expense.
ROBB: Sometimes it's at the expense of the constitutional order. I mean, because, because it's become this logic, I think for a lot of Republicans where if the liberals are getting mad, it must be good, right? This must be something good that we're doing, we're provoking a reaction amongst liberals.
But I think at the same time within that coalition, if you look at someone like Steve Bannon, he's not joking, right? He actually does want Trump to run in 2028. He actually did want Trump to try to stay in office after he lost in 2020. So, so that's where I think it gets dangerous and that's, that's for me why I think you know, let's be serious about this.
DINGMAN: Right, that's the title of your post, Let's Be Serious. Well, I just want to ask you one more question because I hadn't thought about this until I read your post and I'm just curious to get your take on it, because there is this idea a lot of times in modern political discourse that Trump sort of invented this way of communicating as president. But there are some people who feel like Trump's origin story as a politician who was, you know, really intent on actually winning.
Some people feel like the moment that he decided to do it is the White House Correspondents' Dinner in 2011, when then President Obama basically trolled Trump from the podium by making fun of the birther conspiracy that Trump had been advancing, and there's this very famous video clip of Obama making all these jokes at Trump's expense, and the whole room is laughing and then the camera pans to Trump just like stone faced there. So I wonder what you, what you make of that. I mean, we are, it is very common for the media broadly to ascribe the origins of this to Trump, but do you think it was Obama?
ROBB: Yeah, that's, I mean, that's a great example to bring up about just how humor has been used in this era, and I don't know what's what, what Trump is if that motivated, but he clear clearly that in that context was, was Obama releasing his frustrations at having to deal with the constant unfounded birther conspiracy, which I think that's a just a raw, a raw moment that that history will capture of a snapshot into. I don't know, the weaponization of of humor in this era that we're in.
