politics

For a brief moment in 2017, Anthony Scaramucci became a unit of time — his roughly 11-day stint as White House communications director was so fleeting that it entered the political lexicon. Nearly a decade on, he has proved more durable than the joke. The Trump loyalist-turned-critic, Wall Street financier and podcast host remains a fixture in American political culture. He is still parsing the president he once backed and the bets — on figures like Sam Bankman-Fried and on crypto — that have shaped his career.

“We’re six months out from the midterms. I’m curious to get your reading of the political landscape and what you think is going to happen in November.

November’s still a long time off, so it’s very hard to make predictions. 

If you look at Kalshi, it looks like the Democrats will win the House, 1 but the big problem in American politics is [gerrymandering]. Political leaders have the opportunity to redistrict or to cut the congressional districts in a way that could favor their party. We have 435 congressional districts. Approximately 8% of those are up for contest. I think that’s unfair to the American people. 

1 It’s interesting that Scaramucci turns to prediction markets over opinion polls — these platforms have grown in prominence, but face scrutiny over [concerns] about insider betting. Meanwhile, redistricting remains a live fight, with recent escalation driven by a Supreme Court [rollback].

I would just say this rhetorically: Are we in a real democracy where the politicians are picking the voters? I thought the voters were supposed to pick the politicians. We’re in sore need of reform.”

“Could the Democrats end up taking the Senate as well as the House, or are you cautious on that? 

I’m a little bit more cautious on that because [of] the red states that have less population in them. If you’re telling me [James Talarico]) is going to turn the state of Texas purple, where there’ll be one Republican and one Democrat from the state, that’ll be a watershed in American politics. 2”

“These machines, they have created a cartel. They have a duopoly now. 

The two parties, you mean.

The two parties, yeah. They control the landscape. They’ve tightened up their ability to get incumbents reelected. Just imagine you and I opening up a restaurant and our food is terrible. We’re getting one-star Yelp ratings, but we can never get the restaurant closed. We always stay as the two chefs in the restaurant. That’s what’s going on in Washington right now.”

“You are still a registered Republican, right?

I am. Donald Trump hijacked that party. He decapitated what was once known as the Republican Party and did this M&A transaction where he installed this right-wing populist party. It’s called the Republican Party, but it’s really the MAGA party and the personality cult of Donald Trump. When his political personality extinguishes, sometime in 2028, there will be an ideological battle for that party again.”

“Why are you not more active in trying to find that next Republican? You voted for Biden and then Harris in the last two presidential elections.

Trump is too dangerous. It’s funny, all my Wall Street buddies voted for him and now they’re regretting the fact.”

“Are they all regretting that they voted for him?

Most people are.

A lot of them have done well out of the markets.

I’m of the belief that prices are higher. We have an oil crisis. He imposed illegal tariffs, which raised the pricing umbrella for all the lower-middle-income people that voted for him. ”

“He’s put us in a very vulnerable state as a country and an economy. If you want to make the case that the banks have record profits in the short term, sure — but he’s also suing some of the banking executives. 

You are losing the predictive capability of our justice system — what our civil rights are, what our free speech rights are. It’s very, very bad for business. ”

“It’s early. We have to get through the midterms. 

One of the biggest things you need to be president is name recognition. Remember the electorate you’re dealing with. People that are watching your show are very sophisticated. The average voter is really not. 

I think the war is going to hurt people that are close to Donald Trump. [Marco] Rubio and [JD] Vance are going to be victimized by Trump in ways they haven’t totally predicted yet. He’s already started with Vance, with the [attack](on the Pope, because he knows Vance has a [book] coming out on his conversion to Catholicism. 

He doesn’t want to build Vance up into the next president?

No, of course not.

You have to understand the nature of Donald Trump. He wants the Democrats to succeed him, with 100% certainty. 5 We [still] try to normalize him: He’s a Republican, he’ll want a Republican to succeed him. He’ll want Vance or Rubio. He doesn’t want those guys to succeed him. ”

“Let’s say he has a successful remaining two years of his presidency — which seems unlikely. He wouldn’t want those guys taking credit for anything that happened in the administration. 

You met him years ago, didn’t you? In the ’90s in New York.

He would not have remembered that. I was a young man working at Goldman Sachs. My boss took me to see him during the casino restructuring and some of the bankruptcies. [Trump] was looking for financing. 

I looked up to him. I read The Art of the Deal. The rappers sang songs about Donald Trump. We admired his bravado, his risk-taking and image-making. 

Years later, I was working at CNBC as [a] paid contributor. I got invited to the Apprentice parties, we did a couple of fundraising events together and then we started to develop a relationship.”

“In March of 2015, Donald Trump called me. I had breakfast with him. He said, I’m running for president. I looked at him like he was crazy. I said, That’s just like a publicity stunt. He said, Oh no, everybody thinks that, that’s why I’m so low in the polls. But when I announce I’m running, I’m going to go right to the top of the polls. When Jeb comes out of the race, will you come work for me? Right then and there, I shook his hand. Jeb got knocked outta the race in South Carolina, Trump called me, we did our first event in Albuquerque, New Mexico. That’s when I got MAGA fever.

What was MAGA fever to me? Donald Trump was talking to my dad. My dad was born in 1935 in a coal-mining town in northeastern Pennsylvania. He wasn’t college-educated. He went on to become a crane operator on Long Island, spent 41 years in the union, but he had a high-paying job. We had a tiny little house and we lived a good part of the American dream. I would never dishonor my dad by telling you we grew up poor. 

“That once economically aspirational, blue-collar family doesn’t exist in America anymore. These families went from economically aspirational to economically desperational. We blighted these towns. Trump sees something about America that we need to fix.

“Seeing how hard your father worked, and the community around you — had you never thought along these lines before you saw Donald Trump and voters respond to him?

I left that neighborhood. I went to Tufts University, Harvard Law School and Goldman Sachs. I built my own hedge fund business. I got invited to the World Economic Forum. I started hanging out in the salons of the wealthy. You pick up the collective biases of those people.

You forgot where you came from.

Right. There was a man [Trump] that lived adjacent to the Tiffany store on Fifth Avenue, in a triplex apartment that looked like Louis IV smoked crystal meth and decorated. He saw the problems in the neighborhood I grew up in. I missed it.”

“They’re in a circular firing squad. They treat [Newsom] like he’s further to the right than [former Hungarian Prime Minister] Victor Orban.

Cut it out, guys. Focus on principle. Stop attacking each other. Line up. Republicans line up. Ted Cruz wanted to strangle Donald Trump. He lined up with him. You have got to learn to do that in politics. 

But you don’t really like that, about those who’ve lined up under Donald Trump.

“I don’t like it because they’re hurting the country. I don’t like it because they’re subverting the Constitution. If you told me Donald Trump was a transformational, healing, regenerative leader seeking an American renewal and was going to reform America and make it better, of course I’d like it. 

I am optimistic, by the way. I predict you will see a very surprising American renewal, because it’s a very young country. It doesn’t have an anchored culture. It’s an experiment. 

Renewal on the left or the right?

I’m not sure yet. Eighty years after the Revolutionary War, we had the Civil War. Eighty years after that, we had the Great Depression, and the Second World War. Eighty years out from that war, this country is getting dunked. 

We’ve lost our generational memory about the institutions and the processes that matter. Now we need a leader to come in and explain that to the people and say, We have to return to the process. 

Trump is helping us do that, by the way, because he’s so out there doing the opposite that people instinctively know, This is not right. This is why the approval ratings are way down. Trump is forcing the American people to have a moral and cultural reckoning. Every time we’ve done that, we’ve sought redemption and renewal. I predict that that will happen. ”