Jon Gruden has a net worth of $30 million. As an ESPN commentator Gruden earned $6.5 million per year. When he returned to Oakland in 2018 as a head coach, he signed a contract that pays $10 million per year. In September 2015, it was revealed that Gruden is the highest paid personality on ESPN. His highest NFL coaching salary prior to returning 2018 was the $4 million per year he earned from Tampa Bay.
Gruden graduated with a degree in communications in 1985 and was later hired as a graduate assistant coach at the University of Tennessee during the 1985-1986 season. He spent two years as the quarterbacks coach at Southeast Missouri State. Gruden then moved to the University of the Pacific in 1989 as offensive assistant as the tight ends coach, where he coached Scott Lubow, who was second team All Conference. In 1990, Gruden was a special assistant with the San Francisco 49ers under quarterback coach Mike Holmgren. In March 1991, Gruden became the wide receivers coach for the University of Pittsburgh under Paul Hackett. Between 1986 and 1997, Gruden served as an assistant and/or coach for the University of Tennessee, Southeast Missouri State, University of the Pacific, San Francisco 49ers, University of Pittsburgh, Green Bay Packers and Philadelphia Eagles. His first job as Head Coach was with the Oakland Raiders 1998-2001. In May 2009, Gruden was hired by ESPN to serve as a color analyst on its Monday Night Football telecasts, replacing Tony Kornheiser. In 2018 he was re-hired as head coach of the Raiders.