8. Mark Rogowski
Criminal History: Rape, murder
Time Behind Bars: Currently serving a 31-year sentence
The San Diego skateboarding legend known as "Gator" went into a free fall when he was dumped by his then-girlfriend Brandi McClain. After the break-up, Rogowski broke into her home repeatedly and allegedly made several face-to-face threats against McClain's new boyfriend.
When McClain's friend, Jessica Bergsten (a woman Rogowski hadn't talked to in years), asked Rogowski to show her around San Diego, the professional skater obliged. After spending the day together, Rogowski brought Bergsten back to his apartment and, in a twisted act of revenge against his ex-girlfriend, beat, raped, and murdered Bergsten. Rogowski, currently being held at Men's Colony in California, has been in prison since '92 and will not be up for parole again until 2018.