Will Saletan’s Insane Amount of Trump Knowledge Finally Paid Off

Summary

---

The Bulwark Podcast – Can We Get Rich by Watching Hundreds of Trump Speeches?

Date: July 21, 2026
Hosts: Brandon Harnett (A) & Will Saletan (B)

---

Episode Overview

This episode of The Bulwark podcast playfully explores whether having encyclopedic knowledge of Donald Trump's speech patterns can be turned into a profitable betting strategy. Inspired by a recent Kalshee incident involving a teleprompter operator betting on Trump speeches using insider knowledge, hosts Brandon Harnett and Will Saletan conduct a non-monetary, theoretical experiment: they “bet” on which words Trump will (and won’t) say in his upcoming election conspiracy speech. The discussion deftly balances humor, sharp political insight, and an exploration of the predictability and theatricality that define Trump’s public appearances.

---

Key Discussion Points & Insights

1. The Incident that Inspired the Challenge

• Background: A White House teleprompter operator was caught placing illegal bets (with insider info) on which words Trump would say during speeches, sparking discussion about the overlap of political events and predictive betting.
• Brandon’s Framing (00:00):

  “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?”
  The episode then sets up a theoretical wager based entirely on extensive viewing—and internalization—of Trumpian speech habits.

2. Setting Betting Parameters and Ground Rules

• No actual money is exchanged—all bets are theoretical as a matter of ethical reporting.
• Betting on Kalshee-style word markets based on current odds.
• Sam Stein, their editor, challenges them to this Trumpian knowledge test.
• Will asserts, “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.” (00:58)

3. The Obvious Trumpisms: Safe Bets

• Commonly Used Phrases:
  • “China/Chinese” (100% probability according to Will; confirmed as the speech’s “crux”) (01:17, 01:56)
  • “Joe Biden” and “Fraud” (both highly likely) (01:17, 01:56)
  • “Rigged election” (Will: “It’s impossible for him to get through this speech without saying it”) (01:17)
• Low-Payout, High-Confidence Bets: These are the consistent ‘hits’ in Trump’s rhetoric, so the payout is low, but the chance is nearly certain.

4. The “Interesting Territory”: Long-shot Bets and Theoretical Deep-cuts

• Will’s Picks:
  • “Russia/Russian”: (“He’s not gonna say there’s Russian interference, but he might say there isn’t...unlike the Russia hoax...”) (02:24)
  • “Fake news”: (at 31 cents, “If he’s going to do one of his fake...stories, the media is always debunking him.”) (02:24)
  • “Barack Hussein Obama”: (“He can’t resist saying, by the way, Barack Hussein Obama, have you heard of him?”) (02:24)
  • “Transgender”: (“Long shot. But…when he mentions Save America Act, he sometimes adds a thing about transgender.”) (02:24)
• Brandon’s Picks:
  • “Hottest”: (Trump “loves talking about how we're the hottest country in the world...stock market...that’s right now trading at 58 cents.”) (04:06)
  • “Stock market”: Similar logic; Trump reliably boasts about perceived economic strength. (04:06)
  • “Pratt”: (Deep cut. Trump has referenced Spencer Pratt’s “stolen” election. “Could pay out big.”) (04:06)

5. “No” Bets and Predicting Trump’s Avoidance

• Brandon’s No Bets:
  • “ICE”: (“I don’t think he’s going to say ICE...internal enforcement no longer a winning issue.”) (04:06)
  • “Transgender”: (“I just…don’t know…think he’s going to keep the focus on the fraud.”) (04:06)
  • “Israel/Israeli”: (“A lot of tension around Israel lately. Especially during a primetime address, I don’t think he’ll touch it.”) (04:06)
  • “Iran” (three times): (“I think he’ll say it twice, but not three times.”) (04:06)
• Will’s No Bets:
  • “Hormuz” and “MOU/Memorandum”: (“There are issues that Trump doesn’t want to talk about. They’re not going to be on the prompter.”) (07:13)
• Why Avoid These?
  • Sensitive topics or those with recent negative press, or those unlikely in a formal, teleprompted context.

6. The Role of Ad-libbing and Speech Context

• Discipline vs. Instinct:

  Will: “Some of this is, we’re asking how much is this going to be like a standard Trump speech? He would say ‘hottest’ if he were talking to a crowd…but in this context?” (06:45)

  • The chance of off-script remarks (like “hottest” or a Dummocrat slur) increases if Trump ad libs, but is reduced in a formal, teleprompted setting.

• Brandon: “If I was a betting man, I wouldn’t bet on Trump being disciplined.” (07:51)

7. Humorous Commentary on the Exercise

• Will laments not betting on the “Venezuela” or Brandon’s “no” on Israel:

  “I should have taken your bet on Israel. To bet no on Israel was a good call.” (07:56)

• The lighthearted competitive spirit is evident:

  Brandon: “Will, I look forward to touching base tomorrow.”
  Will: “All right, Brandon, we’ll catch up and see who did what 24 hours later.” (08:23–08:39)

---

Notable Quotes & Memorable Moments

• On Betting Culture and Ethics:

  “We at the Bulwark do not bet on stuff that we cover. However…our editor, Sam Stein, demanded that we test our knowledge…” (00:00)

• On Trump’s Patterns:

  Will: “He can’t resist saying, ‘By the way, Barack Hussein Obama, have you heard of him?’” (02:24)

• On the Predictability of Trump:

  Will: “It’s impossible for him to get through this speech without saying ‘rigged election.’” (01:17)

• On Discipline:

  Brandon: “If I was a betting man, I wouldn’t bet on Trump being disciplined.” (07:51)

---

Timestamps for Key Segments

• 00:00–01:17 – Introducing the betting game, setting ground rules
• 01:17–01:56 – The obvious safe bets (“China,” “Biden,” “Fraud,” “Rigged Election”)
• 02:24–04:06 – Long-shot and deep-cut bets; the logic behind each pick
• 04:06–06:45 – Brandon’s “No” bets; debate on likely omissions
• 06:45–07:56 – The impact of ad-libbing versus formal speech, revisiting regrets and near-misses
• 08:23–08:39 – Wrapping up the competition; friendly sign-off

---

Recap: Can You Beat the Experts?

• The episode fuses political humor and analysis—demonstrating that deep familiarity with Trump’s rhetorical style offers little more than theoretical fun (and a window into the strange world of political “prediction markets”).
• Ultimately, the experiment is used to underscore both the predictability and unpredictability of Trump’s delivery—and the uniquely modern blurring of politics, entertainment, and gaming.

---

For Further Reading:
Check out more from the Bulwark at www.thebulwark.com to stay up to date with pro-democracy politics and analysis.

Transcript

[A]

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?

[B]

No, not at all. I stay away from this stuff. Don't. Don't try it in your own home. If anyone out there bets based on what, that's on you, man. We're just, we're just doing a theoretical

[A]

exercise, but 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 or won't say?

[B]

So most of mine are yes bets just because 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% because we know he's going to talk about China. So I took that one. Joe Biden, 79% according to these odds. Crazy. Crazy. Of course he's going to mention Biden because he's going to 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 on those and you do your obvious wins.

[A]

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'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.

[B]

There's one that I'm regretting that I put on my list and then I read a little more about the speech and I thought maybe Venezuela. I mean Trump's not gonna wanna talk about Venezuela, the actual invasion. But because of the whole voting machine smartmatic thing, there's some reporting that indicates he might. So I've missed out on that bet if he does it. But here are the more interesting ones. You start getting below 50 cents on the dollar. So I took Russia, Russia, Russian. He's not gonna say there's Russian interference, but he might say there isn't Russian interference, cuz that was the whole rush. 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 te. But he can't resist. He can't resist saying, by the way, Barack Hussein 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 gonna have to mention the Save America Act. Cause 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 5050 shot that he'll also say transgender. That's my bet. Tell me about your more interesting picks.

[A]

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 are 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 it. 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 going to 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.

[B]

So some of this is we're asking how much is this going to be like a standard Trump speech? Right. Because he would say hottest if he were talking to a crowd. Right. 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.

[A]

So that he says it's currently you can buy Pratt for 8 cents and it'll pay out $1.

[B]

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 MOU or Memorandum, which are, you know, not, not a great deal. 64 cents, 84 cents. The payouts are not great on those. There are issues that Trump doesn't want to talk about. So he's not going to bring them up. They're not going to be on the prompter and he's not going to 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 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.

[A]

You know, if I was a betting man, I wouldn't bet on Trump being disciplined.

[B]

Yeah. 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.

[A]

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?

[B]

All right, Brandon, we'll catch up and

[A]

see who did what 24 hours later.