8. Jack Swagger
This next entry is one of two that falls squarely in the "extremely bad timing" category. In February of 2013, Jack Swagger had just made his return to WWE after being out for 5 months. He was being pushed into a a good position, winning a WrestleMania title shot against Alberto Del Rio thanks to his victory at Elimination Chamber. He had just debuted his Real American character alongside new manager Zeb Colter and was riding a nice wave of momentum. The pair was also involved in some mainstream publicity when they engaged in a war of words with conservative commentator Glenn Beck over the content and tone of their onscreen personas. But on February 19th, all that went down the tubes when the former NCAA All-American was arrested for DUI, after police found marijuana in his car and Swagger failed a field sobriety test, admitting his usage to the police officer. Jack went on to lose his WrestleMania championship match to Del Rio, and then subsequently tapped out in a handicap match when he and Colter challenged Del Rio the following night. One can't help but wonder the different trajectory Swagger's career may have taken had he been able to just say no.