The Journal. - The 'Princess of Darkness' Raising Millions for Trump

Episode Date: August 6, 2026

Almost every night in the White House, President Donald Trump calls his fundraiser, Meredith O’Rourke, for an update. Together, they have raised more than $800 million since Trump’s second inauguration. WSJ’s Josh Dawsey and Dana Mattioli unspool their investigation into the president’s unprecedented fundraising and the political operative behind it. Jessica Mendoza hosts. Further Listening: - The Crypto President: Part 1 - The Crypto President: Part 2 Sign up for WSJ’s free What’s News newsletter. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever since President Donald Trump returned to office last year, he's been advocating for all kinds of special projects. Things like a ballroom in the White House. This is going to be probably the finest ballroom ever built. Or his presidential library for when his term ends. It's going to be most likely a hotel. You know, this concept could be office, but it's most likely going to be a hotel

with a beautiful building underneath and a 747 airfield. Force One in the lobby. There's also his recent Freedom 250 celebration in D.C. to commemorate the nation's 250th anniversary. We'll see the iconic Washington monument illuminated with festive birthday lights to honor the start of this historic anniversary year. These projects all run into the millions of dollars, and a team of Wall Street

Journal reporters has been looking into the fundraising efforts that are making them possible. Here's our colleague, Josh Dossie. Most presidents in their second term in office are not fundraising nonstop like this. It just hasn't been done before. The president's put together this unprecedented apparatus to raise money for all sorts of causes and was really relying on corporate America for much of this money. And as far as you know, how much money has the president raised since returning to office? we were able to piece together at least $800 million,

that he's raised through different vehicles, be it at the ballroom or the library, and some of these are really sizable checks. That's our colleague Dana Madioli, who's also been looking into Trump's fundraising. Many of these companies writing checks have, you know, business before the government. They're seeking federal contracts. They might have regulatory decisions coming down the pike as it relates to antitrust. You know, they are lobbying on different things like appropriations.

And they all know that President Trump is watching who is cutting checks and who isn't. As the Wall Street Journal team kept digging, a picture started to form of Trump's round-the-clock fundraising machine. One that involves high-profile companies and hundreds of millions of dollars. At the center of it is a powerful political operative, whom Trump himself has dubbed the Princess of Darkness. Welcome to The Journal, our show about money, business, and power. I'm Jessica Mendoza. It's Thursday, August 6th. Coming up on the show, a look inside Trump's massive fundraising operation. This episode is brought to you by Accenture.

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Whether you're headed to a music festival or a cottage getaway, you can access hundreds of apps on Google Play right from your center display. explore OnStar Tech Today at OnStar.CA and discover how to take your summer to the next level. OnStar. Better never stops. Trump wasn't always big on fundraising. In fact, when he first entered politics, he campaigned against it. I mean, the creed of core was drain the swamp. If I'm elected president, we are going to drain the swamp in Washington, D.C. And there were these forceful chants at rallies.

the things that the president said in his insurgent 2016 campaign, fewer of them drew the excitement and the palpable enthusiasm from the crowd than this drained the swamp. This outsider message that we're coming into Washington, we're taking on the entrenched interests, we're taking on the lobbyists, we're taking on all the big donors, no longer are you going to have these kinds of creatures controlling America. When he was running for president for the first term, he called political action committee is a scam. And he said he was going to return all the money associated with these outside packs back to the donors, even though this money would have been in support of him. It wasn't just rhetoric. Throughout his first term, Trump resisted having to deal with donors.

And this was his stance for years. I mean, his AIDS, even in the 2020 campaign, sometimes had to cajole in bed to get him to attend some of these events. And he would be complaining, like, why do I have to take photos with all of these people? and then he would give a speech and we, then he would be miserable. And I had several of his eight described to me him being on Air Force One and just complaining relentlessly

about having to do all of these fundraisers. But in the lead-up to the 2024 election, Trump's attitude started to change. Around that time, Susie Wiles, now his chief of staff, convinced him to spend more time talking to donors. Susie convinced him to do call time. And call time is hours that politicians spend every week on the phone calling people asking them for money, right?

Just calling them. Sitting there on a computer, ring, ring, ring, can you give me this? Can you give me this? And so Susie convinced the president to start doing call time every week, a few hours. And then he realized that some of these people, if you made these audacious ask, he said, I want two and a half million dollars. I want five million dollars. Some of these people would say yes. and he suddenly began sort of enjoying the pursuit of getting this money.

Of course, it's normal for candidates to raise money during campaigns. And to be clear, no laws prohibit presidents from raising unlimited sums of money for nonprofits, like the ones used for the ballroom in Trump's presidential library, his super PAC or political issue committees. Nor are they required to disclose who their donors are for most of these transactions. But the amounts Trump is pulling in are under. heard of. More than $800 million since returning to the White House. A lot of the money he's raised goes to political organizations that support him, including about $400 million to a super PAC his allies

have created. He's got this MAGA Inc. pack that lots of different billionaires, companies, individuals support that has a giant war chest that he's very much actively fundraising for. He sends out emails to his donor base. So he's really done a 180 on this and embraced it big time. The money he's raised also goes to nonprofits that then fund issues and projects that Trump supports. One organization that's received millions is securing American greatness, a political committee that highlights conservative issues such as lowering taxes and reducing crime. Another nonprofit, called the Trust for the National Mall, is helping fund Trump's ballroom project.

It's collected more than $34 million since the 2024 election. He's raising money for this ballroom that he's building at the White House. He's raising money for various other construction projects around Washington. He's raising money for his library. That's going to be a 50-story-tall skyscraper in Miami that he is building, not a traditional presidential library, right? He has a garden of heroes that he's building, a statue garden. He's working on a golf course in Washington.

I mean, someone told me that if you want to give money to Trump, there's basically a menu of options, like you would see at a restaurant. Like, do you want to give it here? Do you want to give it here? Do you want to give it here? He's created so many different funds and committees that, you know, you can give to almost anything. A spokeswoman for the president said he is the, quote,

most successful fundraiser in modern political history and that Trump plans to use the money to help Republicans in the midterms and continue advancing private sector initiatives. She said, quote, one thing has never changed. President Trump can't be bought. Let's talk about some of the companies that have donated to Trump. One of the ones that comes to mind is META. Can you talk about META's relationship with the administration, like how it has developed since Trump was reelected? Trump really had a grudge with them about the 2020 election where he alleged that they had interfered in a way that resulted in the outcome of that election. So, you know, META had been very nervous heading into this administration. Given that Mark Zuckerberg, the CEO of Meadow, was such a target of the president's ire. And they've gone to great pains to try to repair that relationship.

And what we were able to learn is that in addition to the $22 million payment that they made to the presidential library through a legal settlement that they settled, they also recently gave $10 million to that Trump-aligned C-4 securing American greatness. These days, Zuckerberg is a regular guest at Trump's fundraising event. So is OpenAI CEO Sam Altman. Last year, OpenAI co-founder and President Greg Brockman and his wife also personally contributed $25 million to Trump's SuperPack. And they're not the only ones. There are a ton of other donors, corporate donors, named in your story. Can you just name a few and the projects that they've donated to? Yeah, we were able to reveal through the story in our reporting that Apple gave a $25 million check for the,

White House Ballroom Project. Microsoft gave around $10 million to that project, and Amazon shipped in around $5 million. SoftBank donated $50 million to the presidential library. And then there were other initiatives that we learned about, too. Freedom 250, which was an organization set up to fundraise for the nation's 250th birthday, raised over $50 million from corporate sponsors. TikTok gave $2 million to that. We learned that Oracle and ExxonMobil also gave more than $1 million to that event. And when

it comes to which of the president's causes to give to and how much, all these companies often have to go through one person. Trump's chief fundraiser. Her name is Meredith O'Rourke. I nicknames the Princess of Darkness and the president

calls her risk because she's such a quote-unquote killer with donors. I spoke to a lot of people at the companies that interact with her. And they all say that she's really charming, very persistent, and she's someone when you see her number come up on your cell phone, you have to answer. Why so much of corporate America has to answer O'Rourke's calls is after the break. Hey, y'all, it's Kelly Clarkson with Wayfair. Ever order furniture online and wonder, what if? Like, what if it doesn't hold up? That sofa was four days old. You should have ordered

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and power your next move tomorrow. Meredith O'Rourke has worked with Trump since the first time he ran for president. During the 2016 and 2020 elections, her deep connections to donors in Florida made her a key ally in that state. She got to know a lot of Trump's operatives and allies from Florida,

much of the White House now, from his chief of staff to lots of his top aides, all hell from Florida. And she was a prominent Florida fundraiser. And then in 2024, she sort of became his chief fundraiser. She followed him around the country. She orchestrated events everywhere for him. And then after he won,

she was sort of planning to slow down fundraising for a while. And the president said, no, I want you. sort of strike while the iron is hot. So for the last year and a half, she's been a key figure in his inner circle. O'Rourke is not a government employee, but she often sits in on meetings

between Trump and corporate executives, taking notes, according to Wall Street Journal reporting. She also travels with top officials in Air Force One. On social media, she's described Trump as a mentor. And Trump and O'Rourke check in frequently about their fundraising progress. Almost every night, the two speak on the phone

about which companies are cutting checks, and which aren't. One public company chairman told me you're either on the naughty list or the nice list because he's watching who is giving. According to people with knowledge of their calls, Trump tells O'Rourke how much money to ask for. For some donors, the ask is $5 million.

For others, it's $50 million. He also gives her names to call, often including people who recently met with him. She'll call up heads of government relations, sometimes CEOs, and she'll say, you know, this is very, very important to the president. He's asked me to call you and ask for this donation. And then it sort of goes from there and they figure out which vehicle to bring it to. Is it the ballroom?

Is it the library? Is it Maga Inc.? Is it securing American greatness? But they all said, like, they have to pick up her call. In exchange for their donations, corporate leaders can get special Oval Office tours with the president or candlelight dinners at the White House or at one of Trump's properties like Mar-a-Lago. Business executives told me, the Wall Street Journal that this administration is much more transactional than prior ones. And several CEOs and board members said they believe there's a link between contributions and access to the president. There's definitely a market change between 2016 from corporate America and what we're seeing now.

If you remember in 2016, there were no high-profile CEOs behind the president during his inauguration. I think, like, the biggest CEO during that point was, like, the My Pillow guy, right? It wasn't Bezos and Zuckerberg and that echelon of people. They weren't writing big checks like we see now. And what is your reporting shown about why these big companies are now so much more willing to give money to the president? These really centralized government power in a lot of ways over regulations, over agencies, and sort of has gotten involved in big decisions that companies care a lot about. And so if you want to stay in his good favor, if you want to be invited to the other,

if you want to be in these meetings, if you want to be in the Rose Garden for these dinners, right? Mirate that work is a key person for you to give money to, to return her calls, and to make sure that she likes you, right? So part of her power here is that she's been designated by the President of the United States to hold this role that really few people have held ever.

Josh had some great reporting about tobacco executives meeting with Trump at a fundraiser and him collecting millions of dollars at that fundraiser. and then shortly thereafter, there were changes at the FDA about different flavor vaping devices. At the time, a White House spokesman said that the FDA's regulatory treatment of vapes is, quote, rooted in recent evidence that is found they can help adults quit smoking. Then, there's contractor Lockheed Martin. In the last couple of years, the company gave more than $10 million to America's 250th anniversary and to infrastructure projects in the D.C. area. that's according to people familiar with the matter.

A company spokesperson said, quote, Lockheed Martin has a long history of supporting projects in both the Washington, D.C. area, and across the country. The spokesperson added that its engagement with the government is guided by compliance standards and follows applicable laws and regulations. In June, the Pentagon awarded Lockheed Martin a defense contract worth up to $35 billion.

A few weeks later, Trump revealed that Lockheed has agreed to pay roughly $5 million toward a new helipad at the White House. Taking a quick step back, is there any type of oversight that looks at what the president does and how he fundraises? You know, we've said before that there aren't any laws that prevent the president from raising this kind of money. But as you said, you know, what Trump is doing is pretty unique. Traditionally, right, you would have a Department of Justice in the public integrity section. That's been all but decimated under this administration and this Department of Justice. I certainly think of Democrats win.

The House of Representatives, based on our reporting, they will be doing some oversight of this. And a lot of these publicly traded companies then could be forced to explain. What were you promised by the administration? What happened about fundraiser? Why did you go? Why did you cut that large check?

And that could be really uncomfortable. So after all your reporting, what do you guys make of Trump's success at fundraising? And the fact that so much of corporate America is now so willing to donate to the president and his causes. I mean, I think we're seeing corporate America act in a way that is just very uncharacteristic of how they typically act in other administrations.

I think if, you know, once Trump is out of office, I can't imagine seeing much of this behavior continue. I think he's such a different president in the way he interacts with companies and what he expects from them. And even, you know, what we've seen in terms of them settling lawsuits with this president, you know, lawsuits that people said were unfounded. I just think there's a different bending of the knee going on that we really haven't seen in some time.

A lot of these companies have made a pretty audacious short-term bet. But to do business with this administration, to have access to his president, we're going to give large checks. We're going to curry favor with him to a degree that really has not been done in weeks of political history with a sitting president. The question is whether or not that's a small, long-term bet for these companies or not. That's all for today, Thursday, August 6th.

The Journal is a co-production of Spotify and the Wall Street Journal. Additional reporting in this episode by Emily Glazer, Marianne, Annie Lindski, and Maggie Severn's. Thanks for listening. See you tomorrow. Want to talk ETS with the people behind them? Join me, Etienne Jean-Cabouchard, on the Upside Ticker Talk. We dive into what's moving markets with timely analysis,

trends, and answers to each. ETF questions you've actually been thinking about. Hit play on the upside ticker talk and elevate your ETF investing IQ. Hey, y'all. It's Kelly Clarkson with Wayfair. Ever order furniture online and wonder what if? Like, what if it doesn't hold up? That sofa was four days old. You should have ordered from Wayfair. With Wayfair, there's no what if. Just style you love and quality you can trust. Visit Wayfair.ca.