Roy brought his son to Princeton-Plainsboro Teaching Hospital when all the doctors he saw about his son's illness failed to find a cause. He demanded that Gregory House be assigned to his case. Lisa Cuddy told him that House was unavailable and hid the fact that House's medical license was suspended. However, Roy insisted and Cuddy assigned the case to Eric Foreman, who was reluctant to act as attending if House was really going to be in charge.
Roy became convinced that the tragedies in his family were due to his great wealth and that karma was evening out the balance. He had already lost his wife and was convinced he was going to lose his son.
When House came up with a terminal diagnosis, Degos disease, Roy refused to accept it. Over the objections of his lawyers and Cuddy, he entered into a financial transaction that was likely to bankrupt him. House thought he was being stupid, but a few hours later, he finally realized Jack had a treatable condition. As his son regained consciousness, it was apparent neither one of them cared Roy was now broke.