Aaron Hernandez
New England Patriots tight end Aaron Hernandez was arrested in 2013 in connection with the murder of Odin Lloyd. He was later charged and sentenced to prison that was also close to his former playing field, Gillette Stadium. After more crimes surfaced against him, Hernandez committed suicide.
Montana Fishburne
Montana Fishburne made her Hollywood debut in a series of X-rated films. However, she probably should have read the contract a little closer, because the film didn't even pay her. It also drove a rift between her and her family, her father being The Matrix star Laurence Fishburne. She also did some time in prison.