One line buried in the agreement may be cause for concern for James, according to a new report from The Daily Beast, which described the contact as "bizarre" and "shadier than it looks."

The contract includes a line that if the judgment is "affirmed" or the "appeal is dismissed," the defendants in the case "shall pay to Plaintiff...the sum directed to be paid by the Judgment plus interests and costs or any part of it as to which said Judgment is affirmed," without a guarantee the insurance company would pay.

This essentially means that Trump will be required to pay the judgment if he loses the appeal but leaves questions about whether the insurance would pay if he is unable, essentially leaving James in the same position as before Trump secured the bond, according to the report.