During his second term, President Donald Trump has raked in cash, soliciting hundreds of millions of dollars toward his political operation as well as his personal projects, such as the White House ballroom or his eventual presidential library. A new report from The Wall Street Journal takes a look at Trump’s extensive fundraising operation, including his often-successful attempts to get some of America’s most valuable companies to shower him and his causes with money. These efforts have been bolstered by Trump fundraiser Meredith O’Rourke, a veteran operative he reportedly calls the “princess of darkness.”
The Journal’s report opens up with a notable anecdote that demonstrates how close the president is to his fundraiser, revealing that Trump calls O’Rourke nearly every night seeking an update on the state of his fundraising operation:
Though O’Rourke isn’t officially employed by the federal government, the Journal notes that she’ll occasionally refer to the president as “the boss,” telling donors in phone calls, “the boss wants this money.”
In comparison, sources familiar with the president’s own comments reveal that Trump has his own nickname for O’Rourke, referring to her as the “princess of darkness” due to her being such a “killer” with donors.
O’Rourke has worked with Trump’s political operation since 2016, working as part of his first two presidential bids. The veteran political fundraiser in Florida was later chosen to lead the fundraising for Trump’s 2024 campaign, a move that prompted one of the report’s more eyebrow-raising anecdotes.
Sources tell the Journal that O’Rourke declined to fly between her northwestern Florida home and the Trump campaign’s Palm Beach headquarters and instead chose to drive six hours between the two locations, which allowed her to be reachable and to make donor calls throughout the lengthy car ride.
Per the Journal’s reporting, prospective donors are often fêted with candlelit dinners with Trump at the White House or Trump’s real-estate properties in Virginia or Florida, lavish events that cost $1 million a head. Attendees told the outlet that O’Rourke is frequently in attendance at the dinners and will relay the donors’ and the president’s remarks to other administration officials. The Journal describes the scene at some of the events, which have included OpenAI CEO Sam Altman and the CEO of Pfizer as guests: