Jameis Winston's Contract Projections Jameis Winston is going into free agency with an increase in his market value well above the contract he signed with New Orleans in 2020. What could a new contract look like for Winston in 2021? Author: Feb 6, 2021 Last offseason, Jameis Winston signed a 1-year, $1.1 million deal to join the New Orleans Saints as a backup quarterback. Winston cited that he joined New Orleans, opposed to other teams, to learn from Sean Payton and Drew Brees after a rollercoaster beginning to his career in Tampa Bay Buccaneers. “Well, we have a Hall of Fame quarterback (Drew Brees) and a future Hall of Fame coach (Sean Payton). That is very intriguing for a young quarterback like myself.”