4 Years Ago
Jeffrey was possessed by a demon that knew Lilith's location, and Sam and Dean tortured him for information. The demon refused to give the information, so he let Jeffrey out momentarily. The Winchesters explain to him that they need information from the demon. The demon returns, and Sam and Dean extract the information and exorcize the demon. Sam and Dean drop Jeffrey off at the emergency room and Dean reminds him not to say anything. Over the years, Jeffrey missed the demon and got involved with alcohol, but was saved by a rehab counselor.
Jeffrey got the idea to summon the demon back, so he visits Nora asking for a summoning spell. She turns him down, so Jeffrey kidnaps her son from his dorm and blackmails her into giving him a spell. The spell doesn't work and Jeffrey sends Nora her son's ear, demanding another spell. Nora finds another one that requires the blood of the person who exorcized the demon. So Jeffrey begins killing women in order to draw Sam and Dean out. He also makes sure that Nora send Sam and Dean to him.
Sam and Dean do follow the trail and visit Jeffery in search of the demon. Sam goes to watch a potential victim, and Dean goes with Jeffrey. Jeffery takes Dean to a warehouse and knocks Dean out. He reveals to Dean that he loved being possessed and plans to summon the demon again. Jeffrey performs the summoning, but the demon goes into Nora's son instead of Jeffrey. Jeffrey asks the demon to possess him again, but the demon refuses. As Jeffrey is about to attack again, Dean shoots Jeffrey.