14. Jeff Hardy
Jeff Hardy's WWE career never hit the heights it could have because of his troubles with drugs. And shortly after he left the company in 2009, police seized his house and arrested him on charges of drug trafficking. What they found were masses of controlled prescription pills - including Vicodin and Soma pills - as well as anabolic steroids, traces of cocaine and other drugs. Within a couple of years, Hardy pleaded guilty to the charges and was thrown in prison for ten days. He was also given 30 months of probation and a fine of $100,000. Both Hardy brothers have had their run-ins with the law (as you'll see later on) and the bad luck has struck Jeff again recently; after he broke his leg in a dirt bike accident last month.