Trump's 'princess of darkness' fed up with his $50M shakedowns: report

President Donald Trump's "princess of darkness" is privately complaining about his increasing demands for more and larger donations from corporations, according to a new report.

The president is in almost nightly contact with Meredith O'Rourke, pressuring her to bring in more money and telling her which donors or companies to hit up next, the Wall Street Journal reported Friday.

Trump has transformed fundraising into a highly personalized operation with himself at the center, keeping track of which donors have given and how much, and regularly pressing O'Rourke to demand larger checks than she originally planned to request, according to the Journal.

The asks are staggering. Some donors receive requests for $5 million, while others face demands for $50 million. Trump provides O'Rourke with specific names to contact, often including people he recently met with in the Oval Office.

O'Rourke has relayed Trump's directives to companies with remarkable bluntness: "This is very important to the president. He's asked me to call you and ask you for this donation." In some calls, she references Trump as "the boss," saying "the boss wants this money."

Trump's nickname for her reveals his assessment of her effectiveness. He calls O'Rourke the "princess of darkness" because she is such a "killer" with donors—a compliment that masks the discomfort her role has created, with the Journal adding, "The president closely tracks who gives, aides said, repeatedly assigning O’Rourke with big asks that she has told others make her uncomfortable."

The fundraising operation reflects a pattern of relentless extraction. When donors give millions and receive calls thanking them, they expect gratitude. Instead, they hear new requests for additional money. In one documented case, an executive was asked to cut a $1 million check just days after attending a thank you dinner for a separate multimillion-dollar donation to Trump's ballroom.

The operation has generated extraordinary sums. Since returning to office, Trump has raised more than $800 million through various political and legacy projects, according to Wall Street Journal analysis.