Oakland Raiders head coach Jon Gruden has no doubt had success in his NFL career, winning a Super Bowl title in 2002, and making five playoff appearances in his career. Some would say that winning a Super Bowl title would be enough to consider you a great NFL coach, but not everybody agrees with that statement.
When Jon Gruden first became a head coach in 1998, he took a team that was 4-12 in the previous season to a 8-8 record. Gruden once again went 8-8 in 1999, and finally broke through in 2000, where his Raiders lost in the AFC Championship to the Baltimore Ravens.