His vendors call him a “career grifter.” His father’s creditors claim he’s a fraud and a serial extortionist who shakes people down with trumped-up threats of criminal charges. With these and other allegations piling up in court records along with judgments—against him, his wife and his businesses—for millions of dollars, his lawyers are abandoning him, saying he’s a deadbeat. All the while, he’s been living in one of the most luxurious mansions in the Bronx.

Meet Ivanka Trump’s longtime friend, matchmaker and business partner, Moshe Lax…

Trump’s relationship with Lax and the mountain of legal and financial troubles—reported here for the first time based on dozens of interviews and public records—raise serious questions about the first daughter’s judgment, even as she continues to serve as a powerful White House adviser. In response to detailed questions sent to the White House and the Trump Organization, White House spokesman Josh Raffel requested more information about this article but did not provide comment.