WASHINGTON—Almost every night in the White House, President Trump calls his fundraiser, Meredith O’Rourke, for an update. Trump asks O’Rourke which companies and donors have cut checks and which haven’t, and for how much. He often asks her to make much larger financial requests than she was planning—for some donors the ask is $5 million, for others it is $50 million. And the president gives her names to call, often including people who have recently met with him, according to people with knowledge of the calls.  “This is very important to the president. He’s asked me to call you and…

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