According to Celebrity Net Worth, Gruden’s first head coaching job in the NFL was with the Oakland Raiders (1998-2001), and from there he went on to coach the Tampa Bay Buccaneers (2002-2009), which he led to victory over his former team in Super Bowl XXXVII. After losing his position with the team in 2009, the former Buccaneers head coach went on to work for ESPN from 2009-2018. According to Sportscasting, Gruden was a commentator on Monday Night Football and used his experience as a quarterback and coach to host his QB Camp.

Jon Gruden’s complimentary careers helped him amass a net worth of as much as $30 million. For instance, he earned $6.5 million each year for his role with ESPN, which Forbes noted meant he was the highest paid on-air personality for the network at the time. Also, Celebrity Net Worth states, Gruden signed a 10-year, $100 million contract (which pays $10 million per year) when he re-signed as head coach of the Raiders (now Las Vegas) in 2018. Before this contract, Gruden’s highest paying coaching position in the NFL was with the Buccaneers, and his salary was $4 million per year.