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Will Saletan
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Brandon Harnett
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Lady Luck
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Brandon Harnett
Monday.com hey everyone, it's Brandon Harnett with the Bulwark. You may have seen the story last week about the White House teleprompter operator who was secretly placing bets on what words Trump would or wouldn't say in his speeches. He was caught by Kalshee and is now facing significant legal trouble for using his insider information to place bets in violation of Kalshee's rules. It got us thinking though. Do you need to know the actual content of a Trump speech in advance if you want to successfully bet on what words he's going to say? I've watched 500 or so TRUMP speeches and my colleague Will Saletan has watched or read just as many. Could we if we wanted to successfully bet on what words Trump is going to say in a speech prior to him giving it? We at the Bulwark do not bet on stuff that we cover. However, our editor, Sam Stein demanded that we test our knowledge of Trump's speeches by placing non monetary wagers on a speech he was going to give. It just so happens that Trump's big election conspiracy speech was taking place that night. What you're about to see is Will and I place fake bets on what words we think Trump is going to say in that speech and a second video in which one of us is crowned the King of Trump speech knowledge. Do you think you could do better than us? Find out. Will, are you a big gambler?
Will Saletan
No, not at all. I stay away from this stuff. Don't try it in your own home. If anyone out there bets based on what, that's on you, man. We're just doing a theoretical exercise, but
Brandon Harnett
why don't we dive on in? So Will, based on what Kalshee's odds are currently showing, what is the first thing that you bet that Trump will
Will Saletan
Or won't say so most of mine are yes bets just cuz they're more fun to me. China, China or Chinese was only at 81 cents on the dollar. I'm like well that's 100% cuz we know he's gonna talk about China. So I took that one. Joe Biden, 79% according to these odds. Crazy, crazy. Of course he's gonna mention Biden cause he's gonna say the election was cheated for Biden. Rigged election was only at 66. I'm like it's impossible for him to get through this speech without saying a rigged election. So I took that one. Fraud, 72%, 72 cents on the dollar. Took that one. Then I started to get to the more interesting ones. Should I tell you those now or you want me to hold off on those and you do your obvious ones?
Brandon Harnett
Yeah, I mean the only two that I had overlap with you on, it seems are China. Which I agree. He's definitely going to say I believe our friends over at CBS News have reported that, that that's going to be the crux of this address. Although we'll see. There's been lots of different reporting about what he'll be discussing. And then obviously also fraud. I don't know if he's made it through a speech recently without saying fraud in any sense. Whether it's election fraud, welfare fraud. Yeah, I feel like those are pretty safe bets. Not going to have a big payout. So what do you have? Getting into the more interesting territory.
Will Saletan
There's one that I'm regretting that I didn't put on my list. And then I read a little more about the speech and I thought maybe Venezuela. I mean Trump's not going to want to talk about Venezuela, the actual invasion. But because of the whole voting machine Smartmatic, there's some reporting that indicates he might. So I've missed out on that bet if he does it. But here's the, here are the more interesting ones. You start getting below 50 cents on the dollar. So I took Russia, Russia, Russian. He's not going to say there's Russian interference, but he might say there isn't Russian interference because that was the whole Russia. He'll say that unlike the Russia hoax, this Chinese interference thing is real. So I'm putting some that at 43 cents. Fake news, 31 cents on the dollar. I'm like, if he's gonna do one of his fake, his phony election fraud stories, the media is always debunking him. He's gonna wanna say the fake news was wrong. At 31 cents. I feel like it's a fun bet. Barack hussein Obama at 22 cents on the dollar. Brandon, if he's talking from the White House and he's doing a formal speech, of course the word Hussein will not be on the teleprompter. But he can't resist. He can't resist saying, by the way, bar Obama. Have you heard of him? So I threw that one in and then the other one that I have is A yes, at 23 cents on the dollar is transgender. Long shot. Long shot. But my argument is Trump is going to have to mention the Save America act because the upshot of all this stuff is elections are rigged against me. We have to pass this thing on. Voter id, he has added to that for folks who don't know gratuitously a thing about transgender. So if he mentions Save America act, there's a more. I think there's a 50, 50 shot that he'll also say transgender. That's my bet. Tell me about your more interesting picks.
Brandon Harnett
Obviously, he's going to say Save America. I just checked. Trading at 90 cents. I'm not even betting on that because there's no real payout there. First one I feel so confident in, he's going to say hottest. He loves talking about how we're the hottest country in the world, how we used to be a dead country, and like, you know, the Saudi Arabian king and other people would tell him that always brings up hottest, whether it's the stock market, the country as a whole, or what have you. I'm fairly certain he's going to say that that's right now trading at 58 cents. That he'll say it relatedly, the stock market is another one. Not that he's going to go on and on about it, but he just loves talking about, oh, we have the hottest country in the world. The stock market is booming. And while he completely dismisses concerns about affordability, he's always happy to talk about the stock market, which, last I checked, is still up. My deep cut that I think will pay out big if he, if he hits is Pratt. For Spencer Pratt in Los Angeles, it's currently at 8 cents. But whenever he's been talking about election fraud recently, he brings up the case of Spencer Pratt and how he was in second place behind Karen Bass. He's been claiming that Pratt was cheated out of it. I think he said that he had the U.S. attorney investigate that and Steve Hilton's election results. And so I just, I feel like he's going to say Pratt, and I believe it'll pay out big. Now, I have a few things where I bet no that he won't say. And the first one is ice. That's not honestly a big payout. It's currently 83 cents that he won't say it. So, you know, less than 20 cents on the dollar of a payout. There's so much bad news around ICE right now. And we've seen like, a few months ago, there was a memo from Tony Fabrizio that was basically like, this is no longer a winning issue for us, especially with, you know, internal enforcement. Also because he's been talking about rebranding it to Nice. So maybe there is a policy announcement, but maybe it's that it's going to be nice. I just, I don't think he's going to say ice. I disagree with you on transgender. I could be totally wrong. I just. I don't know. I think he's going to keep the focus on the fraud. And so he might then add on, you know, we got to pass the Save America act to protect our country from fraud. But I'm just not entirely sure that he's going to say Trans Israel. And Israeli is another one that I don't think he's going to say. Again, same thing. There's been a lot of tension around Israel lately. I think they're going to just want to avoid talking about that, especially during a primetime address. And the last one is, I don't think he's gonna say Iran three times. I think he'll say it twice. That's my bet. But I don't think he'll say it three times. Maybe one thing that was interesting, I'm not sure if it counts Iranian as the same as Iran. I guess probably, but we'll have to see how it pays out in the end. Of course, we're not actually gambling on this. That he won't say Iran at least three times. Is currently trading at 47 cents.
Will Saletan
So some of this is we're asking how much is this gonna be like a standard Trump speech, Right? Cause he would say hottest if he were talking to a crow. I would have bet on hottest and stock market and stuff. Except in this context. So it basically depends if he starts ad libbing. Brendan, your odds are go way up on those. I really like your bet on Pratt because it's. What's it. What do you say was trading at like 8 cents, really low.
Brandon Harnett
So that he says it's currently you can buy Pratt for 8 cents. And it'll pay out $1.
Will Saletan
Yeah, that's fantastic. So I'm betting, I don't think he'll do it, but I like the payout on that also. I should have taken your bet on Israel. To bet no on Israel was a good call. My no bets were Hormuz and, and Mou or Memorandum, which are, you know, not, not a great deal. 64 cents, 84 cents. The, the payouts are not great on those. There are issues that Trump doesn't want to talk about. So he's not gonna bring them up. They're not gonna be on the prompter and he's not gonna bring them up. I had Dummocrat on my list. D u M O crat because he loves to say it. And then I just took it off. Cuz I figured that he might be disciplined enough in this thing that's supposed to be about election security that, that he won't go into that one.
Brandon Harnett
You know, if I was a betting man, I wouldn't bet on Trump being disciplined. Yeah.
Will Saletan
You know, it really depends on to what extent he is reined in by the context of the moment. Because we both know there's all of these lines like hottest. Like, of course he's going to say hottest. Every speech is going to say hottest. Is this a different enough environment for him? Yeah, I don't know. So I'm regretting the Venezuela I should have put in and I think your no on Israel is a really good call. He's just not going to want to bring that up in any way.
Brandon Harnett
So for our theoretical exercise, we are putting $10 on each of these bets. Again, not actually placing them. And we'll see tomorrow after the speech what our payout will be. And who knows Trump best will I look forward to touching base tomorrow?
Will Saletan
All right, Brandon, we'll catch up and see who did what. Hey everybody.
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Brandon Harnett
24 hours later. Well, welcome back. Will, what did you think of last night's speech?
Will Saletan
So not what I expected. I cashed in fine. But Brandon, I just got to say up front, that was like. So I thought that this speech was going to be this controlled, disciplined, like, here, read off the teleprompter. We're going to have a bunch of national security people around you. Stick to the script. Instead, it was way more like a campaign speech than I expected. What about you, Brendan?
Brandon Harnett
I mean, the first few minutes were like really just straight from his regular campaign stump speeches. It felt so disorganized. Obviously we looked into the documents after the fact and they didn't really substantiate any of the claims that he was making. My personal favorite was when, and I'm still a little confused about this. He was saying something about how we rigged the elections in Venezuela. And it seemed like he was saying how he worded it, that we did, that that happened in Venezuela because Hugo Chavez and Maduro are dictators who have, you know, it's been proven, of rigged elections. But the same document that they were citing said that they didn't have the capabilities to do this outside of Venezuela. It was just a mess all around. It was not what I was expecting to say the least. I actually was kind of thinking he would be pretty disciplined and at least make sense. But it seems like the universal reaction, other than a few members of the Freedom Caucus and like, you know, based likely is that he kind of shit the bed there.
Will Saletan
Well, it's, it's like, first of all, I got to say on the Venezuela. I think that's hilarious to me because, you know, we would never rig the elections in Venezuela. No, what we do is we, we take an unelected government and we unilaterally decide to elevate their vice president to the presidency. And we're going to keep her in power as long as she's shoveling oil our way. So we don't, we don't rig elections, we just bypass elections. But Brandon, you're totally right about the, like, it was almost like the national security people said, you know, okay, we're going to put out the documents. You can say what you want to say, but the documents are going to say what they say. And Trump was just like, fine. And he just did his own riff about rigged elections. And although Brandon, he didn't say rigged elections. This is just like, I was, I was sure he was going to say that me too.
Brandon Harnett
I mean, I didn't bet on that because I actually thought that the odds, I think, were pretty high that he was going to say that.
Will Saletan
I was like, I got my feel. Tell me if you had this too. I was like, normally I listen to Trump or watch Trump, and I'm, like, looking for the substantive part in this case because you and I had done our imaginary bets. I'm, like, listening for buzzwords. And then I'm getting frustrated as he goes through and he says, illegal ballots, election meddling. He said they'd rigged their own country's elections. I'm like, damn, you couldn't have put those two words together. So that was what it was like as a Kalshee, better to follow the speech.
Brandon Harnett
Yeah, it definitely. It changed my perspective, watching and being like, oh, if I actually had real money on the line and he didn't say this, I'd be pissed. With that being said, do you care to reveal how much you would have won if in our hypothetical where we each bet $10 on 10 different words, what was your net profit from a $100 input?
Will Saletan
Okay, so I gotta say up front, I was the person who said we should not actually bet because it's unethical to bet, you know, as a bulwark person, blah, blah, blah. And then it turns out I would have made. I would have doubled my money. I would have made 203, putting in 100. So I. I'm kind of regretting financially. Like, I could have bought us lunch if I had actually put the money in. What about you?
Brandon Harnett
I did not do as well as you. My sleeper pick was Spencer Pratt, as you might recall.
Will Saletan
Yeah.
Brandon Harnett
At one point he talked about the L. A Mayor mayoral election, and he didn't say Pratt. And I was devastated. I think I would have had about a 400 something dollar payout from that one because the odds were so low. But he just dodged it. So unfortunately, I only would have made about 21 bucks.
Will Saletan
We could get tacos with that. You know, that would. That would. That would be worth something. I got to say, Brandon, I knew you had Pratt. And when he started, when Trump started talking about the la, he didn't even talk about the California governor's race. He talked about LA mayor. And I'm like, Brandon is totally going to cash in here. And then I experienced vicarious agony as he managed not to say the word Pratt. I felt so bad.
Brandon Harnett
Me too. It was pretty crushing. Even without any actual financial stake, what were your big pay? What were your biggest payouts?
Will Saletan
The biggest payouts I had were Barack Hussein Obama and transgender, which both cashed in 43 bucks. So let me. Let me just say, folks out there know that pundits get things wrong all the time, but you got to understand that even when we get things right, sometimes we get them right for the wrong reasons. There were several words here that I cashed in. So I got. I hit nine out of 10. I hit this. Seven of the eight positives and two of the nos. Brendan. I just got to admit, transgender hit, but not in the way I expected. I thought it would be in the context of this Save America Act. What was the other one? Russia. I thought it would be about the Russia hoax. It was actually about some Russian interference stuff. Biden came up as the Biden Department of Justice. Fake news did not come up the way I expected to, but it hit on one after another. I felt kind of guilty, like I'm collecting in some poor Couchy. Better is not. What about you? Did you hit any for the. For the wrong reasons?
Brandon Harnett
You know, the one that I was most proud of was Iran. Three times. He only said it twice, but. No, I mean, every other one. I didn't. I didn't think he was going to say transgender. Obviously, he did. And then Pratt was my other one. It was kind of to be expected. It wasn't a crazy amount of surprises. Obviously, I got eight out of 10. Right. But they didn't pay out. Well, it definitely did make me think a little more about this case of the teleprompter operator and just how easy it would be if you knew, for example, that, let's say he was going to say, Pratt, if you put a few hundred bucks in there, Maybe even put $1,000 there, you're getting a really nice payout. And I can really see how he was able to make, like, about $100,000.
Will Saletan
Yeah. This operator. Well, first of all, I got to say the Iran thing, saying it twice and not three. They set the betting line, and it has to be three. And now. Now I understand. I don't do sports betting either, but now I understand how they set the betting line because he said it twice. And then we're all hanging on it to see which way you cash in. And then. So there's a reason why they said it at three. The teleprompter operator. So this guy, he knows what's on the teleprompter, but there's never been a president where it's, like, harder to guess from the teleprompter because he just goes off, you Know, it's the Hussein Obama thing. He just throws. That's not on the prompter.
Lady Luck
Right.
Will Saletan
But this poor snook, I wanna say poor schnook, the guy's a crook. He made the fatal mistake of just, you're winning, dude. You have inside information. You have a great racket going. And then he decides that he's going to change his bets in the middle of the speech. And that's how they caught him, isn't it? Like, if this fool had just stuck with his shtick, he would have kept collecting.
Brandon Harnett
He got greedy. He's got to just walk away. He was up big, and I don't know why he couldn't just take that and leave.
Will Saletan
You know, insider trading is a term that we used to think of in terms of the stock market. And so if you weren't in the stock market and you weren't, if you weren't a big player in the stock market, you weren't participating in it. You didn't really understand what it was. I think what these betting sites, what Kalshee and these sites have done is they've democratized it and what they've made it possible for is for everybody else to participate in corruption. I have a feeling that there's just going to be a whole lot more corruption showing up because of betting markets and just so many more people having access to the phenomenon of inside information.
Brandon Harnett
And I know there's like a libertarian argument that somehow this like addresses market asymmetries by allowing insiders to be gambling on these. And then they're like, oh, that shows that, you know, you're getting information that otherwise wasn't public. Personally, I think that's BS just entirely. And pretty crazy of an argument. Yeah, I don't know. I'm like somewhere in the middle and then I'm like, you should be able to do what you want with your money, but obviously not when you have inside information like this.
Will Saletan
So now just for folks out there, Brandon and I don't have inside information. We don't operate the teleprompter. What we do have is a lot of experience and knowledge about this guy. Right. You watch how much of Trump try
Brandon Harnett
to do everything that he's done.
Will Saletan
Everything Donald Trump says that gives you a big portfolio of information to work with when you're, when you're picking these odds here. So you, you made the, you made money for a reason.
Brandon Harnett
It seems that way.
Will Saletan
Here's the question, Brandon. Was it worth it? Is it worth watching Donald Trump 247 to cash in? That Much money.
Brandon Harnett
That's a tough one.
Will Saletan
I mean, we do it for a job, but I don't think. I don't think for an ordinary person, it's worth your while to. To spend the time that you and I, that Bren and I have accumulated watching Donald Trump and everything he says in order to be able to correctly predict some of what he's going to say in the next speech.
Brandon Harnett
Anything else you want to touch on before we wrap?
Will Saletan
I got a little bit addicted. I have to admit. We didn't actually make money on this. When I looked at the fact that I doubled my money, I'm like, should I, like, be doing more of this? Should I, like, do another round of this? Should we put in real money? And then I thought, I feel gross about betting markets, so I'm not going to do it. But I could totally understand, having had a little taste of this, how people get addicted to it. What about you?
Brandon Harnett
No, same. I mean, I was thinking Back to the McKay Coppins piece in the Atlantic about his year where they paid him to get addicted to gambling. And I mean, it totally. It seems totally possible. It doesn't really even feel like gambling necessarily when you're doing it. Obviously, it's a prediction market, but, yeah, part of me kind of wants to make this a series, but at the same time, it feels a little. It definitely feels a little unethical. Even though we don't have insider information, if any Bulwark followers want to use all the information they're learning from us to do it, you know, do what you want with your life and your
Will Saletan
money, I would say to everybody out there, don't try this in your own home. And if you. If you bet on anything Brennan and I have said, that's on you, man. I do not want to be responsible for dragging more people into an addiction.
Brandon Harnett
So, Will, it was great playing with you. Congratulations on your big win. I hope you celebrate with your fictitious $103 profit.
Will Saletan
You too, man.
Brandon Harnett
Thank you, man. Everybody be sure to like this video and subscribe to the feed for more content like this. Until next time, we'll see you guys later.
Will Saletan
Foreign.
Lady Luck
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Brandon Harnett
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Podcast: Bulwark Takes
Hosts: Brandon Harnett & Will Saletan
Release Date: July 21, 2026
In this lively Bulwark Takes installment, Brandon Harnett and Will Saletan embark on a tongue-in-cheek experiment: if you’ve watched hundreds of Donald Trump speeches, can you successfully predict (and "bet" — hypothetically) on specific words he’ll say during a major election speech? Prompted by the real-life case of a White House teleprompter operator busted for insider betting on Kalshee, the Bulwark duo put their Trump knowledge to the test, theorizing profits, discussing the ethics and culture of prediction markets, and reflecting on the addictive nature of political gambling—even when there’s no actual money on the line.
For those curious about the intersection of politics, prediction markets, and the enduring unpredictability of Donald Trump, this episode offers savvy analysis, entertaining banter, and a thought-provoking warning—not to mention a glimpse at how even the experts can get caught up in the excitement of a political gamble.