Carson Palmer
The Raiders went all-in on JaMarcus Russell in 2007 and he became arguably the worst draft bust in NFL history. This left them treading water for a couple of seasons as they tried to find another franchise quarterback. Finally, they pursued Carson Palmer as they lured him from the Bengals. They swapped first and second-round picks for the signal-caller (via Bleacher Report).

It made sense on paper because Palmer worked with Raiders Head Coach Hue Jackson at USC. They also knew each other from Cincinnati when Jackson was their wideouts coach. In the end, it didn’t matter because Jackson received his pink slip after a season. Palmer only lasted one more before he had an Indian summer in Arizona.