Trump vs. The Billionaire CEOs With Tevi Troy

_THE INTERVIEW_

Ari: As an expert on presidential history, what has surprised you most so far in the second Trump administration?

Tevi: I think the energy with which they went about executing their agenda. In the first Trump term, there was a lot of confusion and a lot of infighting. This second term, they have been much more focused, knowing what they want to accomplish.

There are fewer factions. It does not mean there is no infighting, but you do not have the ideological breakdown of three different factions that you had in the last term.

If you sign up for this Trump administration, you know it is a MAGA administration and there is basic agreement on the direction. That gives them the opportunity to get more accomplished, which has sent a lot of people for a loop and left many flummoxed. But I think that is the number one biggest surprise.

Ari: Does that unity extend to all facets of the Trump administration, or are there still breakdowns? For example, in foreign policy?

Tevi: There are some disagreements, but even the people who disagree think they are in the same camp. In the first term, you had the MAGA types, represented by Steve Bannon initially.

Then you had the traditional Republicans, with Reince Priebus representing them. And then you had the so-called globalists or globalist Democrats that Ivanka, Gary Cohn, and Jared represented.

They all had a legitimate claim or argument to say, "Oh, I represent true Trump." In the second term, everybody is MAGA. They are MAGA Trump, and there are disagreements within them about what MAGA means.

But you do not have the globalist Democrats; you do not have the traditional Republicans.

Ari: How does this define Trump's grasp over his administration? He seems to be the one setting the agenda, while people like Bannon and Tucker are on the outside trying to mold what MAGA or Republicanism means.

Tevi: Well, they can do it all they want, but Trump said this in the lead-up to the Iran strike, which I supported. He said, "I define what MAGA is." So when you have an ideology that is around a person, that person gets to define it.

If you find yourself deviating from that person, then suddenly you are, by definition, not part of the movement.

It gives Trump maximal flexibility, which is what he likes. But it will make it hard to determine what MAGA is after he is no longer on the scene.

Ari: I want to hear your thoughts on Trump's relationship with the richest people in the country, the titans of industry you wrote about. At his inauguration, one of the biggest stories was that the richest people in the world were right behind him. How has that relationship played out since?

Tevi: One thing that is super interesting is that they were indeed behind him, but they were in front of the cabinet and the top White House staff. Their positioning was very interesting.

My timing with the book, The Power and the Money, about top CEOs and their interactions with presidents, was very good because the Trump administration sees CEOs and big companies as people to negotiate with, people to make deals with.

I just read that Mark Zuckerberg never talked to Joe Biden. Part of it was that Biden was a little checked out, but usually a president is somewhat in touch with the top CEOs.

They do not all have relationships as tight as some I talk about in my book, like Lou Wasserman and Lyndon Johnson, but there is some contact. It was surprising to me that with Zuckerberg there was absolutely no contact.

Trump is different that way. He likes talking to CEOs; he sees CEOs as his peers. He likes talking to people in the fellow billionaires club. He thinks they are people he can make deals with to get things done for his agenda.

Ari: Just today, he posted on Truth Social his admiration for Tim Cook, calling him one of the best people in the world. Do you think Trump has been getting his way in these relationships and making the deals he wants, or are the CEOs getting the last laugh and taking advantage of him?

Tevi: I think with presidents and CEOs, there is a mutuality of interest. They both benefit from the relationship. If they do not, then you see a big falling out, like with Elon Musk. In general, both sides want the relationship to continue because both sides get something from it.

It is really interesting that you mentioned Tim Cook. He is not a particularly political person, and I do not think of him necessarily as a Trumpy person. But in the first term, and I quote this in my book, he would pick up the phone and call Trump.

Trump said, "That's why he's a great CEO, because he calls me directly. Other people, they'll hire consultants, they'll hire lobbyists, but Tim Cook just talks to me directly," and Trump respects that.

I know in the Bush White House, where I worked, he did not just pick up the phone and call President Bush. There is a whole process and you would have to schedule a call. But with Trump, I heard this great story about a Fortune 10 CEO, a top CEO, who comes to Washington without a plan to meet Trump.

They reach out and say, "Can we come by and see you?" And they say, "Sure," and they fit him in that day. That just does not normally happen with presidential scheduling, which is very regimented in most administrations.

Ari: Who do you think, out of all these titans, is the most politically savvy in the Trump era?

Tevi: When you said "in this Trump era," it might have changed the question a little, but I was about to answer Jamie Dimon because he generally has been very good at playing both sides. He has this phrase that I think is very clever. He calls himself "barely a Democrat," where each word matters.

The Democrats hear "Democrat" and they say, "Great, a CEO in banking is on our side. That's wonderful." And Republicans hear the "barely," and they say, "Well, he's got to be a Democrat because he's in New York and it's a blue state, but 'barely' means that he's against the excesses of the woke left."

When Dimon started in this business as CEO, he would come to Washington twice a year. Now he comes to Washington twice a month. I think he has been very savvy at playing Washington.

Ari: What does someone like Jamie Dimon, who represents a lot of Wall Street, want from Trump?

For a long time, Trump positioned himself as being up against Wall Street, but now it seems they have backed him, saying he would not tank the economy. What are people like Dimon trying to get from Trump, and what has Trump been able to get from them?

Tevi: First of all, I would be wary of saying that he sees himself as against Wall Street. He views the Dow and the S&P as the markers of success. If the Dow is going up, that is good for him, and it is good for everyone who has investments. So he looks to the Dow. I do not think he considers himself as against Wall Street.

In the first term, a lot of banking CEOs and a lot of white-collar industry CEOs were against him and were critical of him. That calmed down in this term. For Dimon, it is not just what he is looking for from the Trump administration; it is what he is looking for from government.

Banking regulations are so complex. They are looking for certainty, clarity, and not to be on the chopping block. They are looking for whatever regulatory advantage they can have. In my book, I talk a lot about how big CEOs and big corporations benefit from regulation because it is a barrier to entry for little guys and small competitors.

Regulation is a subsidy. Complexity is a subsidy. These guys can afford the lobbyists and the compliance attorneys that the younger, smaller competitors cannot. Whenever somebody says we should regulate AI or high tech or banking, they all say, "Yes, and we will help. We will come to the table and regulate with you." Of course, the regulations benefit them and their companies.

Ari: What about Sam Altman and the AI revolution? It is disorienting to keep up with all the changes. Altman is quickly becoming one of the most powerful people in the world. How is he playing the game, and how has Trump's relationship with him evolved?

Tevi: I think he is playing it very well. If you went back a year ago, you would have said, "Uh oh, Sam Altman's having this fight with Musk.

Musk is very in tight with Trump, and Altman's going to be in trouble when the administration starts." Now Musk is on the outs and Altman is the go-to guy on AI. I think Altman has played it pretty well.

But the thing about AI is things are happening so fast. I do not know if Altman is going to be the guy in two years or even two months. You hear all this stuff about how well the Chinese are doing with AI. Maybe we will all just be following them because it sounds like the American AI models are very expensive and the Chinese have figured out a way to do it more cheaply.

It could be like with consumer electronics in the seventies and eighties. America invented a lot of the great consumer electronic innovations, but the Japanese figured out how to do them cheaply.

Ari: Do you think the Trump administration has been able to think about AI clearly? Trump is not exactly Gen Z; he does not keep up with all these new trends. How has he navigated the AI revolution?

Tevi: I agree that Trump probably does not know much about the details of AI, but he has some very smart people around him, both inside the administration and outside advisors, who are weighing in.

Look, as I said, it is moving really fast, so I am leery of imposing too many regulations on it to start. We could end up in a place where we constrain ourselves and the Chinese or some other competitor could lap us on AI.

At the same time, AI is potentially so dangerous that you cannot just let it run amok. It is a very complicated field to navigate.

Ari: So because of how hard it is to navigate, do you think they are just waiting it out?

Tevi: I think you should take a bit of a wait-and-see approach. I like to look at how different technologies have evolved over time. There is a reason they say that we were promised flying cars and we only have 280 characters. Certain regulatory decisions made over the years led to the world we are in.

There were regulatory barriers to, let's say, supersonic transport, which is why we do not really have the Concorde anymore. But at the same time, Clinton and Section 230 and the internet legislation he passed in 1998 led to the development of basically the FANG stocks. The web developers benefited from that regulatory scheme that gave them a lot of latitude.

Other industries, like not just supersonic transport but also nuclear energy, have suffered from too much regulation and too many lawsuits, and we are behind in those areas. So small regulatory steps that happen now at the nascent stage of an industry can have huge impacts 20 or 30 years from now on how technology develops.

Ari: Let's talk about Elon Musk. His close involvement with Trump during the election was fascinating, but then he seemed to flame out and disappear just as quickly.

Why do you think Musk's relationship with Trump deteriorated so rapidly, and has he put himself in a bad position moving forward?

Tevi: Well, the mantra of Silicon Valley is "move fast and break things," and I think Musk is definitely in that mode. I think that has served him well.

If you look at the Walter Isaacson biography, he will go to the production line and say, "Why are you doing this? It seems inefficient." If somebody says, "Well, we've always done it that way," that is not the right answer if you want to stay employed in an Elon Musk company.

He is willing to change things, break things, and stop existing traditions. That works for him and it has made him perhaps the richest man in the world.

At the same time, if you move fast and break your relationship with the President of the United States, that is hard to repair. I think both of them have an interest in reconciling, but it is going to be hard to repair what they have torn asunder at this point.

Ari: What about Elon Musk moving forward, past the Trump administration? Has he lost political capital for whoever comes next, even a Democrat? Do they see him as less trustworthy than another CEO of his type?

Tevi Troy: He is in a bit of a hard position. Not that I would not trade bank accounts with him. He supported the Democrats in 2012, 2016, even 2020. It is only 2024 that is the first time he supported a Republican, but he did it in a spectacular and very public fashion. And then he has this falling out with Trump.

The Democrats were so irate with him. Remember, people were defacing Teslas, and he was public enemy number one. I think it is hard for him to get back in the good graces of the Democrats. At the same time, as long as Trump is around, it is going to be hard for Republicans to embrace him as well.

I think he is a little politically homeless. It goes against the advice that I offer in my book, The Power and the Money, about how to deal politically. What I argue is that you want to dial up the engagement. I say go up to 11 if you can, if you like the Spinal Tap reference. But you want to dial down the partisanship.

Jamie Dimon, as I mentioned, does that. He is very engaged with Washington, but he tries to keep his partisanship to a minimum. That is the strategy to staying in good graces with both parties over a long period.

Another lesson I have in my book is that in any one interaction, a president is more powerful than a CEO. But a CEO can outlast a president and be there for multiple presidencies.

So if you are a CEO, your strategy has got to be about staying power. And if you are a president, your strategy is going to be about wielding the maximum power that you have to deploy in a very limited time of four or eight years.

Ari: Going back to Jamie Dimon, you talked about trying to be as non-partisan as possible. During the peak of the woke era and the country's division, that must have been very difficult.

It seemed like every moment, with Black Lives Matter and the riots, demanded a statement from every CEO. How did Dimon manage that?

Tevi Troy: A smart strategist would recommend to these CEOs, even in the mix of the racial reckoning of 2020, that you have got to take a step back and think about it before you jump in and make a pledge with every new development. I think some of the CEOs took steps that did not serve them well.

You think about Rob Manfred and Major League Baseball. I think he lost a lot of capital with Republicans by moving the All-Star game from Atlanta. I heard Brian Kemp, the governor of Georgia, speak, and he said he told him, "Don't do this, Rob. This is a mistake. Don't succumb to the crowd." Manfred did not listen, and I think it has really hurt Manfred and baseball.

Then you look at Bud Light or some of these companies that went with the woke craziness in their marketing. That did not serve their companies well.

Ari: How about Mark Zuckerberg? When we started Upward News on Instagram, mass censorship suddenly happened around the pandemic and the BLM era.

Everyone on the right started to hate Zuckerberg. Then he went on Joe Rogan, seemed to acknowledge what he did was wrong, and stepped away from content moderation, unbanning Trump.

Has he successfully rehabilitated his image?

Tevi Troy: I think he in particular has a tough time with this. He is so hated on the left, and there are obviously people on the right who did not like him either. I have got a great story in my book about a Facebook lobbyist trying to convince a Democratic lawmaker to go to dinner with Zuckerberg. The lobbyist says, "You come to his DC house, Sheryl will be there, it'll be great."

The lawmaker says, "You don't understand. I don't want to meet them. I'm not friends with them. I'm not interested." I think that is an attitude among many Democrats. As I said earlier, Biden did not even meet with him once. He said at one point, "I don't like Zuckerberg."

So I think Zuckerberg is particularly radioactive on the Democratic side. But not every CEO reaches that level. He has a tough hand to play.

Ari: Are there any underrated CEOs who are really crushing it but do not get a lot of media attention?

Tevi: Well, yes, but because they are not in the headlines, they are just doing an effective job. Look, CEOs have a choice. They can focus on the inner workings of the company, or they can be more public players.

Being a public player has its advantages, especially if you get in a regulatory battle. But at the same time, if you run afoul of an administration, that could hurt you and your company.

Ari: You pushed back on my point about Trump positioning himself against Wall Street. But there is a big populist fervor in his movement. A natural part of populism is to go against the titans of industry and champion the common man.

Has Trump's populism lost some potency because of his close relationships with these CEOs?

Tevi Troy: I do not know if I disagreed with you so much as I suggested being careful not to go too far on the anti-Wall Street thing. Trump obviously has a strong populist streak, he is good at it, and I do not think he is going to let that go.

I just do not see Trump becoming one of the elitists. His brand is this populist, regular guy approach, even though he is a billionaire. He manages to make it work, so populism is going to continue to be his approach.

Ari: But does it actually manifest in policy? A few years ago, Jeff Bezos was the enemy of MAGA, and the left and right united to rail against him and Amazon.

A populist leader might try to make Bezos bend to his will. Now, there seems to be no problem between them. Does Trump's populism only exist in his rhetoric?

Tevi: Look, the way Trump speaks publicly is a bit of an act from what I hear. If you meet Trump personally, he is the most gracious person.

He will say, "Oh, you like a Diet Coke? Can I get you a Diet Coke? Do you want me to send some Diet Cokes to your house?" He is very kind in person from what I hear, but he has got this persona of the tough guy and the populist.

I do not think it would preclude him from having conversations with CEOs that he rails against, if they are still willing to have the conversation.

In some ways, it is all like professional wrestling. He sees it as a bit of an act and is willing to have that conversation. I do not know if you know, Hulk Hogan just died, and he really became famous in the movie Rocky III when he does this wrestling exhibition match against Sylvester Stallone as Rocky.

He plays a horrible person, really mean and cruel. Then at the end of the fight, after the fight is over, he and Rocky are all buddy-buddy. So, like with professional wrestling, which is a bit of an act, I think some of Trump's bluster is an act. Behind the scenes, he speaks differently to people.

Ari: Last question about the Trump administration. What are some underrated things we should start watching?

Tevi Troy: I think you correctly noted the foreign policy divide, and that is going to be a bigger deal as we get closer to 2028 and we look for a successor.

Also emerging new technologies. We talked a little bit about AI, but how we are going to approach them. Do you take a populist approach or a more libertarian approach?

In general, what is going to happen with the MAGA movement? At this point, it looks like JD Vance is probably the favorite, but maybe I would take the field over him. What happens as you get closer to 2028? Do he and Marco Rubio still work well together? Or does one start leaking against the other?

Does one leave the administration? Obviously, it is harder for a vice president to leave. It is more normal for a Secretary of State to leave. I think some of those issues about what happens after Trump are going to get more and more interesting.

Ari: I can't believe I didn't ask you about JD Vance. The way Trump uses him as a dealmaker, sending him to do real work, seems so different from the Biden administration, where Kamala Harris was sent to do things that did not seem as important.

Is there anything novel in how Trump decided to use the vice presidency?

Tevi: Well, it is a bit of a test. You see how somebody performs and then you decide what to give them. On election night, Trump said to JD Vance, "We put you out there against every tough interviewer, every biased, liberal, slanted journalist, and you did great in all of them." So he kind of passed that test.

With Kamala, she did a poor job. Every time she had an interview, the Biden administration had to do cleanup. It is actually a little surprising given that JD Vance had a very rough first week of his launch, but he really turned it around.

By the end, he was doing the most interviews of all four nominees, presidential and vice presidential. He was really giving it to the liberal media when they were asking him biased questions and kind of proved himself in the crucible of the campaign in a way that Kamala was never able to do.

Ari: So it is literally just The Apprentice happening before our eyes. There was that story before Vance was picked for VP that Trump sent motorcades to every possible person they were considering.

It was this whole spectacle. It is funny to see Trump still thinking in that theatrical, Apprentice-like way, even now in the White House.

Tevi Troy: In many ways, his administration is kind of like Thunderdome, right? Two men enter, one man leaves.

You just see it play out. In the first term, and I wrote a book about infighting in the White House called Fight House, Trump said, "I like conflict." He is willing to let his advisors fight it out and see what happens.