Getty Dallas Cowboys quarterback Dak Prescott. There has never been a player in NFL history like Dallas Cowboys quarterback Dak Prescott when it comes to making money. In terms of getting the bag, Prescott’s path from a fourth round pick in the 2016 NFL draft to signing the richest NFL contract of all time — twice — is probably something that should be studied in business schools. To recap, Prescott became the NFL’s first player to make $40 million per year when he signed a 4-year, $160 million