Jameis Winston has generated his wealth primarily through his lucrative contracts with NFL teams. In 2015, he signed a four-year contract with the Tampa Bay Buccaneers worth $23.35 million, with a signing bonus of $16.7 million. In 2020, he signed a one-year contract with the New Orleans Saints worth $1.1 million. His current contract with the Cleveland Browns is worth $5.5 million for one year.