Jackson has one of the most interesting stories on this list. The quarterback is a divisive figure because some people think he’s one of the NFL’s most overrated players. But the former MVP saw Patrick Mahomes’ contract and wanted a massive deal too. However, the Ravens resisted meeting his demands.
Many people called him naive because he went into negotiations without an agent. In the end, Jackson proved that he was a brilliant businessman because he achieved a five-year, $260 million extension. This also made him the highest-paid NFL player on a per-year basis (via CBS News).