8. Rich Gannon
Gannon had a difficult start to his NFL career. The quarterback failed to fully convince in Minnesota or Kansas City before joining the Raiders. Indeed, his Chiefs coach benched him in the postseason because he didn’t trust him. But Gannon became a bonafide starter in Oakland and even won the 2002 MVP award.
The Raiders made it to the Super Bowl that season. Their fans have one memory of that season and it’s not a good one. Gannon threw multiple interceptions against the Bucs (via Missoulian). Meanwhile, Tampa sacked him five times as he suffered a nightmare. He indeed lacked protection on the day but it was still a terrible performance. This event stained his entire legacy.