In 1990, Jon began his career in the National Football League when he landed a job with the San Francisco 49ers as an offensive assistant. Able to work side by side with the likes of George Seifert, Mike Holmgren and Ray Rhodes, Jon became a "West Coast Offense" man.
The following year, Jon took a one-year hiatus from the NFL to become the wide receivers coach for the University of Pittsburgh under legendary head coach Paul Hackett.
When Mike Holmgren left the 49ers in 1992 to coach the Packers, he fulfilled a promise and called upon Jon to become his offensive assistant. In 1993, Gruden was promoted to receivers coach.
After three years with Green Bay, yet another former 49ers coach called Jon. From 1995 to '97, 31 year old Jon served under Ray Rhodes with the Philadelphia Eagles as the league's youngest offensive coordinator, where he learned to deal with the egos of Randall Cunningham and Ricky Watters (practice for Keyshawn?). In his three seasons with the Eagles, his offense never finished worse than fifth in the NFC in rushing, and lead the conference in passing in 1996.
In 1998, Jon became the third youngest head coach in the 40-year history of the Oakland Raiders. Since moving back to Oakland following the 1994 season, the Raiders had not had a winning season. Jon quickly changed that, however, as the Silver and Black improved to 8-8 his first two seasons, and winning the AFC West the next two seasons.
In his first season in Oakland, Raiders running back Harvey Williams took note of Gruden's arched eyebrow and lop-sided grin, and dubbed him "Chucky" after noticing a resemblance with the evil doll in the horror flick "Child's Play".
Maybe it was his four years in California that earned him the exposure, but in 2001, People Magazine named Jon Gruden as one of their 50 Most Beautiful People. Knowing he would be the butt of jokes, Jon grinned and yelled, "You don't like it? Well, I don't give a s***, because I'm one of the m***** f****** most beautiful people on this planet!"
On January 14, 2002, the Tampa Bay Buccaneers fired head coach Tony Dungy. It only took just over a week for Dungy to find another head coaching job as the Indianapolis Colts hired him to replace Jim Mora. After failed attempts to hire Bill Parcells, the Tampa Bay Buccaneers lured Gruden away from the Raiders and named him the Buccaneers seventh head coach on February 18, 2002. It wasn't cheap though. The Buccaneers gave up their first and second-round draft picks this year, their first-round pick next season and their second-round pick in 2004. Also, the Buccaneers have to pay the Raiders $8 million over the next three years.
But, it seems to be a win-win-win situation. The Raiders are pleased with the compensation received, the Colts are happy with their new coach and of course, the Bucs are looking forward to much success with their new coach. All three teams reached the post-season in 2002. The Bucs, at 12-4, finished with their best record in franchise history, the Raiders, at 11-5, had the best record in the AFC and earned home-field advantage and the Colts, at 10-6, returned to the playoffs following a disappointing 6-10 season in 2001. The Bucs and Raiders won their respective conferences to face each other in Super Bowl XXXVII. The Buccaneers routed the Raiders 48-21 to bring the city of Tampa their first championship in any professional major league sport.
Gruden's father, Jim, is now a regional scout for the San Francisco 49ers. His brother, Jay, played Arena Football with the Tampa Bay Storm, winning four championships, and is now the head coach of the AFL's Orlando Predators, winning championships in 1998 and 2000. Sherry Gruden, Jay's wife, worked in marketing for the Buccaneers from 1993 to '96. Jon and Cindy Gruden have three sons, Jon II, Michael and Jayson.