In a March 2004 interview with USA Today, Ross said that he has known Trump since the 1970s, when he was a lawyer in a firm with which Trump was negotiating a deal. They became friends, and Ross represented Trump in several major real estate deals in the 1980s and 1990s. In 1996, when Ross had become bored with his legal practice, Trump offered Ross a job.
Ross said of his boss, "I think I know his mind as well as anybody else. I know what he wants. He gives it to me, and I can take it from there. He does not micro-manage. He deals in broad strokes. I love it." Trump said of Ross, "He's tough, firm but fair, a very brilliant lawyer, and I trust his judgment."