26. Ray Perkins
Perkins enjoyed a coaching career that lasted for almost 30 years. His best success was with the University of Alabama, who he led to multiple bowl games. Meanwhile, he also enjoyed time in the NFL. Most of his work there was as an offensive coordinator for the likes of the Patriots and the Raiders. But he was also a two-time head coach. Perkins’ first spell was in charge of the Giants, then he took over at Tampa.
There’s no nice way to say that his tenure as Bucs’ head coach was nothing short of a disaster. He traded away Steve Young to use Vinny Testaverde as his starting quarterback. Meanwhile, his team suffered infamous chokes against the Raiders and the Cardinals. They led by 20 and 25 points respectively in both games but proceeded to lose. With an overall record of 19-41, Perkins definitely overstayed his welcome in Florida.