Bane Jessup was a dangerous and charming mob boss and a temporary love interest of Prue Halliwell. In 2000 he worked with the demon Barbas to kill thirteen witches and was later sent to jail. He escaped later that year when he was targeted by the demon Litvack. After vanquishing Litvack, Bane willingly returned to prison. While a dangerous criminal, Bane also seemed to possess a kinder side, as shown when he forgave a man who failed him, and in the fact that he truly cared about Prue. He also admitted that he didn't choose this life for himself, stating that he had other dreams.