#3 Jake ‘The Snake’ Roberts
One of the few men in WWE history to win a Wrestlemania match after one month of his debut, Jake’s on-screen creepy, villainous character was a hit with the fans across the States, leading to increasing levels of popularity.
After a few short-term stints at wrestling promotions across the country, he returned to the WWE through their sponsored drug rehabilitation program in 2007. He was enrolled in the program due to constant drug and alcohol struggles, which left his bank account in tatters.
Family members close to the legend said that he even contemplated suicide during these tough times. To makes matters worse, Roberts was reportedly diagnosed with cancer.
However, it was Diamond Dallas Page that would come to the aid of Roberts by taking him into his home rent-free to finally get him to overcome his addiction urges. Today, Roberts is in the WWE Hall of Fame after years of recovery but his finances are still on the rocks.
