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Security program on spreadsheets, new regulations piling up and audit dread. It's time for Vanta. Vanta automates security and compliance, brings evidence into one place, and cuts audit prep by 82%. Less manual work, clearer visibility, faster deals, zero chaos. Call it compliance or call it compliance. Get it? Join the 15,000 companies using Vanta to prove trust. Go to vanta.com calm I'm Charlie Sykes. Welcome back to the to the Contrary podcast. We should start with a couple of headlines that are that you have to say is this actually real life New York Times headline? You've heard about this, but the IRS to drop audits of Trump and family as part of the deal. Officials vowed not to pursue any matters including those involving President Trump's tax returns that are pending. So apparently he's getting a forever immunity for himself, his family and his business. This is the same deal that Trump cut to create the $1.8 billion slush fund that he's gonna use. Which by the way, here's the other headline from the New York Times Prison to pardons to payouts January 6th rioters are elated at Trump's $1.8 billion fund. The possibility that people who ransacked the Capitol could get cash from the government they attacked is the latest head spinning twist in President Trump's effort to rewrite the history of January 6th. Meanwhile, Republican voters are okay with that. Donald Trump's revenge tour gets Representative Thomas Massie's head on a stick. Massie's apparently unforgivable sin was that he broke with Donald Trump in on of all things, the Epstein file cover up. Donald Trump has also endorsed the scandal infested Ken Paxton in the Texas Senate run off. But Ken Paxton is a MAGA loyalist running against incumbent John Cornyn, who is presumably somewhat well liked by other Senate Republicans who now have to spend the next six months looking around at all of their colleagues, their Republican colleagues who have been exiled by Donald Trump. That might create something of a morale and a political problem. And, of course, Donald Trump is still stuck in his war of whimsical in Iran. Let's try to sort all of this out. And joining us on our podcast this morning to sort all of this out is Phillips o', Brien, who's a contributor to the Atlantic magazine and an American historian and professor of strategic studies at the University of St. Andrews in Scotland. So thank you, first of all, Ferdinand, for joining me from across the pond on a rather, you know, yet another extraordinary week. So thanks for coming on the podcast. Appreciate it.
- [03:59]
Phillips O'Brien
Corruption Palooza Week, I think we'll call it.
- [04:02]
Charlie Sykes
All right, so let's start, let's start with that because, I mean, you know, there are people who are going, boy, this is really, really kind of, you know, shocking that you're having this kind of blatant, brazen, naked corruption. You made the point. I think it was yesterday on Substack. No one should be surprised because corruption's kind of the first principle of Trump 2.0, isn't it?
- [04:23]
Phillips O'Brien
Well, I mean, it's been going on even before he took the inaugural oath, from what we can tell that I mean, what have we seen? We've seen payoffs for pardons. We have seen crypto deals done with the family. We have seen luxury jumbo jets donated to him. We have seen the Board of Peace, which I call the Board of Corruption, set up, which is a financial organization that he controls. We have seen just money. We've seen insider trading clearly done on oil futures done on information that had to only come from central authorities. So this has been corrupt. The administration is corrupt. It's not like there is corruption there. It is corrupt. That is the way it does business. So this is simply, I think, where we're heading. You might say it's slightly more brazen than some of the stuff before, though even that's arguable. But it is what the US Is. And I think people acting shock, shock don't want to face reality. This is nothing new. Now, this has been going on for a year and three months. This is what the American government is face up to it and deal with it.
- [05:39]
Charlie Sykes
Well, but that's the hard part, right? How do you deal with it? You know, Donald Trump has essentially been like the burglar who goes down the hallway, you know, at the, at the hotel. And he's. And he's trying all the doorknobs to see what's open. And he figures that I can get away with this, I can get away with this. And it feels like he's keep dialing it up so that what you have this week was just this naked raid of the treasury, taking taxpayer dollars and putting it into his own slush fund. And it certainly. And part of the problem of dealing with it, and I think is this the ongoing surprise or shock is, is how are we going to deal with it? This is a president who feels that he is above the law, will not be held accountable. He's being gifted this money by the Department of Justice, which no longer serves as any sort of an independent agency. It's basically now an accomplice of Donald Trump in enriching himself. So isn't that part of the reaction is that you become almost numb because you fed the feeling that he's going to get away with this and nothing can be done about it?
- [06:42]
Phillips O'Brien
Well, this is the great worry I have, really. The great worry, Charlie, is the people say, oh, we'll come back from this. Well, actually, how do you come back from this if you don't have legislation that changes things and is enforced? Because we do have the emoluments clause. I mean, that is in the Constitution. But fat lot of good that does. We're supposed to have the Justice Department to investigate these things, and fat lot of good that does. Even Congress is supposed to be a check on the president. Well, in this case, fat lot of good that does. So the US System has failed. I mean, what Trump has done is expose the US System for being extraordinarily weak in this one area, and that if you have a president with a majority in Congress that will back you, you could basically do whatever you want. There's no restraint. So unless there is some way that the American system can recover from this, and that is really going to have to take a constitutional amendment, maybe, or strong new legislation, I think we have to deal with the fact that the presidents have a blank check to be corrupt going forward. The only thing that's held them back in the past has been norms that they just. No one decided to do this because it was considered so horrible. But Trump has said, who cares? I don't care what your norm is. My norm is different, and I'm going to take all the money I can. And that will be a very difficult thing to undo, if not impossible.
- [08:03]
Charlie Sykes
I worry that you're right about all of that. It also does feel, though, that. And let's kind of just put this in a larger context that, you know, where Trump is in his presidency, because the nakedness of the corruption also suggests that he's kind of at that YOLO phase of his presidency. You only live once, and he's going to get away with it. Now, this is in the middle of the midterm elections where, you know, I mean, the conventional wisdom is that Republicans are in deep trouble. Donald Trump's poll numbers are, you know, continue to crater, go from one low to another. And yet, instead of doing anything that would make him more popular or that would help his political party, he's doing things that feel like he's setting it on fire, as if, okay, you know, I only have a small window now, and I'm gonna take care of myself, which is interesting, because, you know, he demands absolute loyalty of Republicans. And I wanna get to that in a moment. And yet, clearly, Donald Trump does not give a shit about the Republican Party. Right? I mean, you know, he's having some of these victories in these primaries, but I don't feel that they feel like winning. So you spend tens of millions of dollars beating Thomas Massie in a, you know, plus Trump, 35 district, great win there. You endorse a guy like Ken Paxton, which may put the Senate majority in play. So just give me your sense, because it kind of feels as if Donald Trump is just feeling like he's completely, you know, you know, not governed by any of the laws of political gravity, much less morality.
- [09:32]
Phillips O'Brien
I think people like Trump can believe two completely conflicting things at one time. For instance, I think he knows he's going to die relatively soon, but he also thinks he's going to live forever. There's this sort of dual nature, and that's what we have in the election. I think part of him absolutely understands there's a chance the Republicans lose very badly in November if the free election occurs. And I still think people are somehow assuming that will occur when it might not, and that there's a chance the Republicans get thumped, which is why he got that Justice Department proviso saying he can't be investigated. I think there are preparations in place in case the Republicans lose the majority and there are presidential pardons waiting on the table. But then there's the other thing, that he actually believes that he can control the Republican Party, and the Republican Party will back him and things politically. And he's got a lot of evidence for the fact that the Republicans will fall him down. The corrupt rabbit Hole that he can, there's nothing he can do, nothing he can do, get the party angry at him.
- [10:36]
Charlie Sykes
Okay, well, here's the catch 22 though. Yes, he is in absolute control of the Republican Party, but the Republican Party is, you know, shrinking. So he is content not to persuade the majority of Americans to change their views on this. He just wants to have a Republican Party that's absolutely locked in with him. On the other hand, if you're a Republican, what you need to survive is perhaps, you know, the ability to, you know, do the smart thing is to distance yourself from Trump. So while Trump is racking up these victories for himself, he is making it harder for Republicans to win the election. Right. Because any Republicans are thinking, you know, I probably, you know, this war is really unpopular, the gas price is really unpopular. I really want to distance myself from the Billion dollar Ballroom. You know, I don't want to go along with the, you know, IRS immunity thing. You, you can't do any of those things. So he has shackled the Republicans. They not only can't do the right thing, they can't do the smart thing. Right.
- [11:37]
Phillips O'Brien
Well, in his mind, he's won three presidential elections. You know, one was stolen from him. He's still wildly popular. From what I've heard, he's been, does not believe the polls that say he is unpopular. He believes that's not true. Cuz he gets fed polls from certain Republican groups that, that tell him that he's doing really well so that there's, there's different narratives going on in his head. And when push comes to shove, I think what we see is all he cares about is loyalty.
- [12:02]
Charlie Sykes
Yes, I think it's good.
- [12:03]
Phillips O'Brien
Just, are you someone who will do anything I ask you to do, no matter what? I mean, Pam Bondi failed the loyalty test probably because she might not have agreed to this deal. You know, she wasn't willing to go down the full Trump route and that's now not negotiable for him. There's utter complete loyalty where he can tell you exactly what you have to do and that's all that matters.
- [12:27]
Charlie Sykes
So this makes the Paxton Cornyn thing a little bit more problematic because Cornyn, of course, may not be full, full heron fire MAGA, but he voted with Donald Trump 99% of the time. He's gone along with the complete agenda. He's in Senate leadership. So when Donald Trump endorses against an incumbent senator in a primary like this, I mean, he's obviously going to piss off, you know, other Republicans that he, that he actually needs. But I think the definition of loyalty keeps changing because Ken Paxton and I mentioned this to you before we started doing this. I asked AI give me a list of all of Ken Paxton's scandals. And my printer just kept going on and on and on to say that this guy. I mean, you know, Donald Trump has picked a guy who is perhaps even, you know, not even more, but almost as corrupt and immoral as he is. Somebody willing to violate the law, somebody who is, you know, took a leading role in trying to overturn the election. And I. And I guess. And I wanted to bounce this off you because it almost feels like a little bit of. Little bit of, I don't know, maybe going a little bit too far where. Why would he pick Paxton over Cornyn? Because Paxton is the kind of guy that would help him pull off a coup. Cornyn might not.
- [13:55]
Phillips O'Brien
Yeah, Paxton. I mean, Cornyn might as well. But as you say, Cornyn votes with him 99% of the time. He believes Paxton will be with him 100% of the time. So it's one of those things that there's loyalty and then there's complete devotion. Right. Cornyn has been loyal, desperately loyal, trying to show Trump that he is loyal, whereas Paxton is.
- [14:18]
Charlie Sykes
Paxton is willing that they see each
- [14:20]
Phillips O'Brien
other like co criminals and they know that each will do what the other needs.
- [14:25]
Charlie Sykes
See, that's the key is the gloss on loyalty. That loyalty is no longer like, you will support me and vote for me and pass my legislation. Although apparently Trump is really mad at the Senate leadership for not trashing the filibuster and passing the SAVE act and, you know, dragging its feet on the billion dollar Ballroom. So this is basically kind of an F you to John Thune as well. But the new loyalty is, will you commit crimes on my behalf? And he looks at Ken Paxton and says, absolutely. Are you kidding me? This guy will do anything because he's already done anything. And you know what?
- [15:00]
Phillips O'Brien
He's right. I think he's right on that. You know, he knows Paxton will do whatever he asks Paxton to do.
- [15:05]
Charlie Sykes
All right, so let's switch gears the other moment. Donald Trump really prides himself on projecting power on the national stage and the international stage. He imagines himself as this world be striding colossus. He goes to China. My sense is that he did not come out of China looking as strong as he thinks he did. So give me your quick take on what happened and what did not happen with that summit last week.
- [15:36]
Phillips O'Brien
Basically, Trump came out inferior to Xi that the United States, if You look at the honest results of the Trump Xi summit, the United States is an inferior power to China. Now that Xi said one thing, clearly do not support Taiwan. Taiwan is our issue. And what happens after this? Trump starts distancing himself from Taiwan immediately. So Xi asks for something, and Trump tries to appease him desperately. Trump asked Xi supposedly for help on Iran. Xi says stuff it. In fact, as it turns out, I don't know if you saw that New York Times story a few days ago. Iranian oil is still getting to China in tankers. These tankers are still getting it through. Not all of them, but some of them. And Z has put no pressure at all on Iran. From all we could tell, if anything, he's gone closer to Iran. So he gets microchips, advanced microchips. He promises to buy a small amount of soybeans. Who knows whether they'll agree to it. So if you look at to the actual balance of interactions here, Trump got nothing. And he's already trying to appease Xi. So that just shows that he has put the United States globally in an extraordinarily weakness position. A lot of it has been exacerbated by this ridiculous war that he cannot get out of and has left him scrambling to find some kind of solution. And until he finds that solution, he really is, he is beholden to China, and he's got to have some kind of good relationship to Xi. So the United States is not the world's dominant power. Now, I think we have to face that right now. China has the whip hand over Trump because Trump has put the United States in an extraordinarily weak position. It did not have to happen.
- [17:25]
Charlie Sykes
This is a shocking thing. I mean, this is, what you're saying here is, you know, ought to be shocking to Americans and because what you're describing is an America in decline. But in America, the chose decline in some ways because it was not inevitable that we would do it. And that Donald Trump, who says that he's gonna make us more respected and stronger in the eyes of the world, is actually presiding over the hollowing out of American leadership.
- [17:53]
Phillips O'Brien
Absolutely. I mean, what did he do last week in Europe? He withdrew troops from Poland. That actually it's been the one country the US has been praising, that he's been praising. So he basically shafts the Poles and he shafts the Taiwanese. Who gets it under Trump being a Democratic ally just leaves you open to get the. The crap kicked out of you. That's what he does. They don't believe the US Is their ally anymore. I was at A European security conference last week, very well known one in Estonia. They would speak to American officials with a polite smile. But in private, Europeans are like, the US Is not our friend. This is not a situation where we can rely on the US and by the way, the Taiwanese think this, Japanese think this. Now the United States has gone up for completely insane reasons and blown up its alliance system. And that means when Trump goes to meet with Xi, he doesn't have his allies behind him. He used to go and meet with Xi with the Japanese behind him, the South Koreans behind him, the Taiwanese behind him, good relations with India, good relations with the Vietnamese, even. All of that's gone. And he goes as a supplicant to the Chinese saying, please help me with Iran. And the. The Chinese just toy with him. They even say the great Thucydides trapline that Z starts talking about. This is a dangerous time because we're rising and you're falling. And Trump is too stupid to understand what Xi says.
- [19:18]
Charlie Sykes
Yeah, but it triggered him when it was explained to him. And then he had to put out that long post saying, no, President Xi, by the way, this was pretty good. President Xi was referring to Joe Biden, because Xi told me that the United States is the hottest nation in the world, which I. I don't know about you, but I don't think that she actually said, I think the United States is the hottest country in the world. I'm just skeptical about that.
- [19:40]
Phillips O'Brien
Yeah, I think. I think. I think Trump's too scared of Z to even bring it up. Yeah, I don't. I think, you know, Trump to. Trump basically took what Xi said. He took all the insults, took him on board, smiled sweetly, and he said, you know, we have a lot of Chinese food restaurants that was trying. Xi was. And Trump was talking about Chinese restaurants in America. And I think that sort of explains the balance of power between the two of them. But I don't think Trump said a word. I think Trump was just desperate to get along with the Chinese.
- [20:11]
Charlie Sykes
Oh, I think you're right. And, you know, I'm an amateur Trumpologist. I thought the body language was very, very revealing with Trump just clearly looking like he was subservient to Xi, but also that when he came back, he immediately changed the subject and he spent the weekend putting out these AI slop and things. You know, if this had really gone well, Trump would be talking about it, he would be touting it. And so it's always a tell what Trump wants to talk about, but also what he does not want to Talk about. Right. So let's go back to this, because I think that this didn't get as much attention as it deserved. You know, Trump had announced that they were. We were withdrawing some troops from Germany because he was angry at the Germans for not, you know, for comments that they had made about Iran. What was the. Why would we suddenly, without any notice whatsoever, pull out of Poland? Because this did send shocks. I mean, Congress didn't know about it. Even Republicans in Congress were unhappy. People in the Pentagon didn't know about it. No one consulted any of our former allies. What's going on there?
- [21:19]
Phillips O'Brien
Because it's in Putin's interest.
- [21:20]
Charlie Sykes
It's so naked, you know. Yeah, yeah.
- [21:24]
Phillips O'Brien
Basically, what the United States is doing is trying to shaft its democratic allies into Europe and help dictator Vladimir Putin. And Putin loves the fact that Putin doesn't want the US to fully leave NATO because he wants Trump to have influence over European countries, but he wants to just make it clear to European countries that they've been abandoned by the United States and they can't count on the United States so that he can potentially bully them. And that's all this is. I mean, this was Trump or Hegseth appealing to Trump, basically saying, okay, what's something we can do? We can keep these troops from going in. And by the way, you're exactly right. Europeans were blindsided. Congress was blindsided. Senior US Diplomats were blindsided. They had no idea in Europe this was coming down the pike. And watching them try to defend it, as I did last weekend, was just painful because they just had to lie. I mean, that's the thing about Trump. He forces you to either lie or be a criminal or both. That's the only way you can work.
- [22:20]
Charlie Sykes
And shockingly, there are people who are willing to do that. Though apparently the Europeans have given up. I mean, you really do feel that this has been a consequence. There was a breaking point. Do you agree with Anne Applebaum that the threats against Greenland was that line in which the Europeans just decided, okay, the sucking up, the diplomacy is not going to work. We just have to. We now have to come to grips with the fact that America is not our friend. That even though a lot of people thought, well, he's just trolling, he's just making it up. That had, you know, that was the moment at which the alliance.
- [22:56]
Phillips O'Brien
Yeah, I mean, they should have accepted it earlier, but they didn't. They basically spent all of 2025 desperately trying to suck up to Trump. I mean, they really did. A lot of them, and they really had this weird argument, we could bring him around if we're nice to him, if we do the right thing and if we give in to him somehow he'll be good to us. And they spent all of 20, 25 debasing themselves.
- [23:17]
Charlie Sykes
Really.
- [23:18]
Phillips O'Brien
Europeans really humiliated themselves. And now number of European leaders. And then for Trump to turn around and basically threaten to shoot Europeans. That's what he, he was talking about invading Greenland, seizing Greenland, which meant he would have gone to war with Denmark. Made even, I think those that had had hope of a good relationship for Trump to realize, you know, nah, it's not going to happen. And by the way, the Iran war finished it off because the Iran war had, has much greater negative impact economically in Europe than in the usa. Huge economic impact in Europe because Europe gets all its oil from the Gulf or a lot of its oil from the Gulf. And for Trump to basically start a war which is going to screw Europe economically without consulting, without thinking through and by the way, stringing it out, what he's doing now is devastating for Europe because he's keeping the oil from coming out of the Gulf, he's keeping the prices high. And that is translating directly to European consumers in a far more dramatic way than to American consumers. I think that's what the Europeans see. He'll kill us if he wants to and he's going to make us suffer economically if he wants to. And we get nothing out of this relationship now. So I do think most Europeans understand it's over.
- [24:35]
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- [25:05]
Charlie Sykes
Security program on spreadsheets. New regulations piling up and audit dread. It's time for Vanta. Vanta automates security and compliance, brings evidence into one place and cuts audit prep by 82%. Less manual work, clearer visibility, faster deals, zero chaos. Call it compliance or call it compliance. Get it? Join the 15,000 companies using Vanta to prove trust. Go to vanta.com calm. Well, I mean, one of the canaries in the coal mine that I find absolutely fascinating is watching, you know, the Italian Prime Minister Meloni, who was, you know, probably one of the most Trump adjacent, or at least friendly European leaders. And she has been, I mean, she's been kind of fantastic in her rejection of what Trump is doing in Iran, but also in standing up for Ukraine. I mean, it's just watching her rhetoric, rhetoric, you can really get a sense that if she is this critical of Trump, what must be going on in every other capital in Europe.
- [26:09]
Phillips O'Brien
Yes. I mean, by the way, the other good thing politically is now attacking Trump is popular in Europe. European leaders realize that standing up to Trump is not an unpopular position to take because Trump has destroyed American standing. The United States is less popular than Putin's Russia in some cases. It's certainly less popular, popular than dictatorial China in European countries. So he has created a situation where standing up to him is actually a positive, even for people like Meloni, who tried very hard. She was one of the ones in 2025 who really tried to keep good relations with Washington. Trump praised her. She was like, we have to stand together. All this pro NATO stuff, as if the alliance was still going to go on. And then finally, I think she's just understood that there's nothing to be gained from Trump. He's just going to, he's going to take what he wants and he's going to leave you in the lurch. And what has to happen is Europe has to stay together. I mean, that's, I think the understanding too here is that Europeans have to really act together now.
- [27:12]
Charlie Sykes
So I want to get to Iran in a moment because you have a really great piece out today about Donald Trump's quagmire there. But, but Donald Trump continues to give do these major favors for Vladimir Putin, who is not having a great month, is he? And we've lost a little bit of focus on what's going on with Ukraine and Putin. I mean, there was a while there where Donald Trump was saying, Ukraine has no cards whatsoever. They're going to have to come up with a peace deal. All of that seems to have faded away. But also give me your sense, can you update us on Vladimir Putin? Because we're seeing drone attacks on Moscow. We are seeing the lack of real progress. Some of the casualty numbers coming out that would suggest, I mean, horrifically hard numbers. So, you know, what is the status of Vladimir Putin and his attempt to crush Ukraine, even with Donald Trump's support?
- [28:16]
Phillips O'Brien
Well, last time we talked about is Ukraine taking the initiative a bit. And I think we can say there have been some really interesting signs on that in the last two weeks. And it goes back. Let's start with Putin at his big victory day parade on May 9, which was by the way, a damp squib, cuz he was clearly terrified. It was only 45 minutes, there was no weaponry. He got in and out. But Putin could only have that victory day parade because Trump interceded on his behalf with the Ukrainians. And Trump said to Zelenskyy, please let, let Vladimir have the parade and he'll release 1,000 prisoners. Which by the way, he's only released 200. So it might be that they paid a fast one on Zelensky. So we have the parade and then Putin launches this really brutal attack on Ukraine, hits an apartment building, kills a lot of people. And in the past, that's often what would have been the situation. But what the Ukrainians did two days later was launch a mass drone attack on Moscow. And even though Moscow is ringed by anti air force, I mean Moscow is probably the most covered city in the world with anti air systems. The Ukrainians are now able to get their systems into the center of Moscow and hit strategic targets. And if they can do it now, they can do it again because basically their systems are getting better. And the Russians are struggling to keep up with what they can launch. So that is the sign they couldn't have done that a year ago. A year ago when Putin had killed 24 people in an apartment building. The Ukrainians couldn't have really responded like this. And by the way, they also responded humanely. They didn't attack Russian apartment buildings, they attacked Russian strategic targets. But they were able to reach out and touch Putin in the center of Moscow. And that is a trajectory sign of what the Ukrainians could do, which they couldn't do before. So the Russians are doing what they've always done, Ukrainians are doing more. And as you say on the battlefield, we just have confirmation the Russians cannot move forward now.
- [30:07]
Charlie Sykes
So what does this mean? Yeah, so what does this mean for Vladimir Putin? Because obviously when you have an attack on Moscow, everybody can see it. That's sort of like, it's hard to propagandize your way out of that. There are all these reports of his paranoia. There are people who have been, it feels like the more criticism domestically of the war that we're hearing. So what do you make of these reports of Putin's paranoia and the vulnerability that's kind of hard for him to have the public ignore?
- [30:41]
Phillips O'Brien
Well, I think the problem he faces is his narrative of the war is unraveling, that he's been telling the Russian people for years everything's going great. We're winning. Ukraine is doomed. We're marching forward. And he was telling specifically the people in Moscow, in St. Petersburg, your life is great. I'm protecting you. The material comforts of your life are going to remain high, blah, yada, yada, yada. So the narrative was the war is going well, and that's what dictators like to do. But that narrative is unraveling. It's clearly unraveling when the Ukrainians can reach out and hit target. It's now in the center of Moscow and caused some real economic damage in the process. So that is the problem he faces, is to keep the Russian system going, he has to project success. That's what dictators do. Dictators say, allow me.
- [31:33]
Charlie Sykes
Always winning.
- [31:34]
Phillips O'Brien
Yeah, always winning. And he's clearly not winning at this point. So, I mean, I don't know if he. I just read the reports like you do, Charlie, but knowing how paranoid he is by nature and how worried he is for his own safety, I can imagine that he is spending most of his time in heavily secure areas in bunkers, because he's tried to kill Zelensky. So he's assuming the Ukrainians are trying to kill him, because that's what he would do if he were the Ukrainians. And so he's probably spending a lot of time in the bunkers.
- [32:03]
Charlie Sykes
Yeah, that's always healthy. Okay, let's switch to Iran. You have a piece out yesterday that Trump is twisting in the wind. And I know it's kind of a, you know, sort of a cheap shot to talk about Taco Tuesday, although it's become a thing now, right, that, you know, Donald Trump announces. I mean, this was really something. He put. He puts out that. That announcement. The clock is ticking. You know, we will, like, wipe Iran off the map again. And then the next day, you know, like clockwork, he says, well, no, I talked to three autocrats in the Middle east and they talked me out of attacking, so I have called off the scheduled attack. So where are we? It feels, as you've been pointing out in the last seven weeks, really nothing has changed. Right. And yet. And people are sort of realizing that
- [32:52]
Phillips O'Brien
Trump wants to get out. That's what he's actually quite desperate to get out of this war, but he can't, because he's got nothing from it. He basically, if he leaves now, he admits that Obama had the best deal possible with the jcpoa and he blew it up and has gone to war and achieved nothing. So he's desperate to get something from the Iranians that he can Use to call victory. The Iranians are not playing ball with him. They are not like the Republicans in Congress. So they're not giving him what he wants. And that's why he goes on this ridiculous pantomime. As you said, it's a continual process. Yes, I will blow up Iran and destroy its civilization and destroy its power plants. Oh, no, I won't. Negotiations are going really well, so we don't have to worry. And by the way, usually they make insider trade deals at that point. Cash in on the falling price of oil. So there's a three step process. Threaten, say things are great, cash in and then get back to threatening.
- [33:48]
Charlie Sykes
So that's been the process, but it's getting old, right? People are, you can't keep bluffing and bluffing and bluffing before people go, yeah, we're not going to play with it.
- [33:57]
Phillips O'Brien
The oil market system didn't react at all. They stayed up at 100. Brent crude stayed up at about $110 a barrel.
- [34:05]
Charlie Sykes
As you're right. For once, the oil markets took Trump's claims for the BS that they are. I mean, that was a pretty clear message. Yeah, that was a noticeable change, a
- [34:17]
Phillips O'Brien
10 second drop and then they were right back up. They had that instant reaction, ooh, maybe things are well. And then they thought, now let's drop.
- [34:23]
Charlie Sykes
Boom.
- [34:24]
Phillips O'Brien
As I said, it wasn't long enough for even to cash in on the insider trading.
- [34:31]
Charlie Sykes
So we are also having a certain level of recognition that the much touted blockade, the US Blockade will take much longer to work than Trump originally claimed. And apparently it's dawning on them that just bombing is not going to achieve Trump's strategic goals. So where are we? We're stuck, right? I mean, there's still a blockade, but it's not as easy and quick as Trump seemed to believe.
- [34:58]
Phillips O'Brien
No, Trump didn't know. I mean, I don't know whether it's because he wasn't told or simply because he refuses to believe anything or whatever, but the blockade was never going to be a short term. Blockades take a long time. They take months and years to have the effect you want them to have. So it's not like you can just all of a sudden it's like Iran is going to instantly run out of the money the day you start the blockade. And by the way, the blockade isn't even perfect because the New York Times had that piece saying Iranian oil ships are still getting into China and they can find ways around the blockade. So the blockade will certainly hurt Iran. I mean, that's not arguable. It's going to take a long, long time to do that, many months. And the Iranians are calculating, and I think in some ways the Iranians sensibly calculating. Trump's got a problem with the November election before they're going to have a massive economic crisis, and that they're going to try and outlast Trump before he really desperately needs something to end the war before the November election, which is not that far away. We are now in the second half of May. We're getting on to June. We're really only five months, five and a half months from the election.
- [36:11]
Charlie Sykes
Yes, but there's always Cuba, right? I mean, if you're about to taco out on Iran, you need something to show you're strong. And again, we all see the signals that they're sending. So he's hoping that, what, by the fall, we're all talking about the liberation of Cuba rather than the failure in Iran. Do you think that that's their thinking?
- [36:35]
Phillips O'Brien
I think that's definitely a possibility. Knowing the way Trump acts, that if he ends up taking a really bad deal with Iran, which he might, because he has got no other alternatives, then you go down the other way, you throw a dead cat on the table and say, look at that, and the next thing will be Cuba. So I could definitely see Trump doing that. That is the way he's behaving and has behaved in the past. At this point, I don't think the American people will really go for it. But you never know. I mean, he would have lost the Iran war more decisively, more quickly than any war in US history, would easily be the easiest, fastest loss of a war in American history.
- [37:14]
Charlie Sykes
That's a hell of a framing. Just talk to me about that, because, I mean, that is a pretty grim verdict.
- [37:21]
Phillips O'Brien
Yeah. He starts bombing on February 28th. He throws in the towel a bit with a ceasefire on April 7. So he only fights for six weeks. Then he's left the storm stronger, hardline, more hardline. Iranian government is in power. He's shown the United States to be a paper tiger in the Middle east, run down American stocks. He's shown allies in the Asia Pacific area. The United States can't fight for them vis a vis China. It's a catastrophic strategic development. He's got nothing, absolutely nothing, out of this war. And it was exposed to be that very quickly in a matter of weeks, shown to be. And that's where we are now. We're basically left in this situation where if this war ends now, at the present status quo, it is a catastrophic strategic defeat for the United States in a very short period of time in
- [38:11]
Charlie Sykes
terms of what the American people will accept and what they will think generally. I think sometimes we overplay the significance of foreign policy in terms of domestic politics. On the other hand, this is, you know, this is clearly having a domestic impact. The gas prices, the price of everything going up, the supplies. And my sense is, not being an expert, is that the worst may be yet to come. So that Donald Trump may think that he can just, you know, press the button and change the subject, but if gas prices and the price of beef and other things keep going up, then he has not solved his political problem. And once again, this is a political problem of his own creation. You want to talk about an owner goal, this is something, and the public seems to understand this with rather startling clarity that Trump has done this.
- [39:03]
Phillips O'Brien
I think that's, that's why this is the most unpopular early stage war in U.S. history. There's been no. Usually Americans rallied around the flag in the first few months, so there's been no rallying around the flag. The price of oil has skyrocketed. There's never been a, you know, a clear strategic justification for the war. I mean, now it's all about Iran's nuclear weapons, weapons. But that wasn't the issue when the war started. But as you say, it's going to have massive economic impact and that's what the Iranians are calculating on. The Iranian government is making the case he can't keep this up forever because oil prices will go up, everything will stay up, and the Republicans will collapse in the 2026 elections if this goes on. But it's hard to see how even now, by the end of the summer, prices go down. That, that the markets are starting to think now, okay, this is going to be a long term change in things. And there's so much backlog in the oil business where all this oil has just not been moving, that I think Trump has really boxed himself in on that situation, which is, yeah, it's his war. He chose it, he's done it to himself. And now he's left desperately trying to get a victory that he can sell to the American people.
- [40:11]
Charlie Sykes
It wasn't all that. Well, let's go back to where we started in the conversation, because it does feel as if one of the themes of the 2026 election might be. It is the corruption. Stupid. Because you have this juxtaposition of 70% of Americans who are concerned about their personal finances. And here you have a president who is obsessed about his ballrooms, that nobody wants the bombs for the war, that nobody wants the insider trading, the amount of money that has put into his own pocket. I mean, frankly, it shouldn't be that hard. I don't have a tremendous amount of confidence in Democrats messaging shouldn't be that hard to make the juxtaposition of does he actually care about people like you? Especially when he gives you a soundbite like the one from last week? That no, he never thinks about the financial condition of the American people. He doesn't think about anybody but the amount of money he has made for himself and what he is doing and what he's forcing Republicans to vote for compared to the average daily life of Americans. I mean, this is, I've seen politicians out of touch before, but this is, this is like world class. For a guy that claimed that he was the voice of the forgotten American.
- [41:23]
Phillips O'Brien
I don't know why the Democrats don't make this issue number one. I would make corruption issue number one because it's so egregious, it's so in your face and so much money. And then it fits everything else. It fits the affordability argument. I have no money to buy gas, but Trump has a billion dollars. I don't have no money to buy beef, but Ballroom is going to cost a billion dollars. So you can make all these different arguments.
- [41:48]
Charlie Sykes
It's almost too easy to the affordability.
- [41:51]
Phillips O'Brien
They just have to make this the issue. But I would think, and you can tell me, being in America, are they getting that? Because this is the issue the Democrats have to run on now because it just boxes the Republican make every Republican candidate. Do you support the $1.7 billion deal to the Trump family? Do you support the permanent fact that the IRS can't look at your thing? Do you support the $1 billion ballroom and ask get every Republican on record for those.
- [42:21]
Charlie Sykes
And the extraordinary thing is that Donald Trump is forcing them to go on record on those things. It's like, I agree with you completely here, but it is Donald Trump who is forcing them. We want to have a vote, an up or down vote, so that every one who's going to be on the ballot will have to take a stand on each and every one of those issues, which is an extraordinary moment. No, I mean, there are some things like I know that a lot of people say, you know, Democrats should run on democracy. Okay, they've done that. And I'm not opposed to that. But, you know, and others say, well, maybe we should just focus on kitchen table issues. The corruption issue connects the dots, the stars align. We're not hungry. I understand all of the differences between us and the Hungarian system and the level of Hungarian corruption, but that was the theme that toppled Viktor Orban. And Donald Trump seems to be like a one man machine. It's like, you need a talking point. You need another example of my corruption here. I'm going to give it to you on a daily basis. And I think he figures maybe people won't connect the dots. And plus, you know, the Epstein files are still out there. And I just. It's. And, you know, I mean, and obviously he's so deeply invested in that. That's what the Thomas Massie thing was. So if he's doubling down on the ballro and these sorts of things, his. The reflecting pond, the Golden Arch and all of those things, does he honestly think he's gonna turn public opinion around by having a big. It is sort of like the autocrats who put on the big parades. But you've seen that he wants to have the biggest Fourth of July fireworks display in world history, set a new record. Like that's gonna do it, right? That will turn people in Donald Trump's mind. If I build a big golden arch, if I build a ballroom and I fire off fireworks, that maybe they'll love me again. Or does he care about that anymore? Who knows?
- [44:15]
Phillips O'Brien
I don't. This is the. I don't know what he cares about. He certainly cares about his historical reputation because he wants the arch. He wants that Golden Arch where he can probably put Trump on the arch. I think he ultimately believes he can sell anything to the American people. And that's the thing about. He sold January 6th.
- [44:36]
Charlie Sykes
He did.
- [44:36]
Phillips O'Brien
I don't think that was possible.
- [44:38]
Charlie Sykes
No, I still don't. No.
- [44:40]
Phillips O'Brien
When January 6th happened, I was one of those people said, okay, at least Trump is done. This is a horrible, sad moment in American history, a tragedy. But the one good thing from this is Trump is now done and discredited. And next thing we know, four years later, he's President of the United States, stealing billions of dollars in front of everybody's face. I suppose if you do that as Donald Trump, you believe you can do anything. Well, I mean, what can't you do? You can have your people storm the Capitol, and now you're gonna give them all, you know, hundreds of thousands of dollars each for whatever he's gonna give them.
- [45:12]
Charlie Sykes
If you would have told anyone on January 7 that Donald Trump will be president again and he will pardon the people who attacked and beat up the cops. And he will create a fund where not only will they not be held legally accountable, he will actually pay them your tax, the people who attacked the Capitol. And so yes, his success in inverting history, turning that upside down mean people who saw it with their own eyes should have a visceral reaction to this. And maybe many people, and obviously many people do not enough. But he clearly thinks that he can not enough, not enough, and not the people who count. Phillips o', Brien, thank you so much for all your time and your insight in another area. Extraordinary week. I appreciate it very much.
- [45:58]
Phillips O'Brien
Oh, it's great. Come on, Charlie. Thanks for having me. Really enjoyed it.
- [46:01]
Charlie Sykes
And thank you all for listening to this episode of to the Contrary podcast. Once again, if you've been listening to us, you know how important it is to remind ourselves that we are not the crazy ones. Thank you.
- [54:04]
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Charlie Sykes
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