4. Marques Tuiasosopo
Believe it or not, Marques Tuiasosopo had one of the shortest and one of the worst careers in Raiders' history. It all started when he was drafted by the Raiders in 2001 and while he would remain on the sideline for around two years, he would finally get significant playing time during a Monday Night football game in 2003 where he threw 226 yards in the second half.
While that might not sound like much, it was enough to secure him the starting job for the first time in his NFL career, which meant he would finally have his chance to show what he could do. Interestingly enough, all he could do was throw for 65 yards, one interception and manage to get injured before the end of the game, making him one of the worst quarterbacks in Raiders' history.