19. Matthew Stafford
In 2017, the Detroit Lions tied up Stafford for five years by making him the then-highest paid player in the NFL. He signed a contract worth $135 million now that guaranteed him the starting quarterback role for the next half a decade. While Patrick Mahomes has changed the landscape for franchise quarterback contracts, this was huge news at the time.
But the reality is that Stafford wasn’t and isn’t worth that much cash. His record over the past few years against winning teams is atrocious. Stafford should have been a building block for the franchise, but instead, he took up salary cap space without helping the franchise move forward. Stafford isn’t in the same bracket as tier one quarterbacks like Mahomes, Lamar Jackson, or Deshaun Watson.