|“||Did you ever think that maybe I loved being possessed? Did you? I loved the connection, the power... and I loved him. Love of my life, actually.||”|
4 Years AgoJeffrey was possessed by a demon that knew Lilith's location, and Sam and Dean tortured him for information. The demon refused to give the brothers information, the demon lets Jeffrey out momentarily to stop Sam and Dean from hurting him. The Winchesters explain to him that they need information from the demon and to get it they will have to inflict great pain and injury. Jeffrey gives them full permission, the demon returns, and Sam and Dean extract the information and exorcise 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.
|“||I was nothing before he found me. A shadow. Too scared to do what I was brought here to do, too timid to live up to my true potential.||”|
Jeffrey got the idea to summon the demon back, which prompts him to visit 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 exorcised the demon. So Jeffrey begins killing women in order to draw Sam and Dean out. He also makes sure that Nora sends Sam and Dean to him.
Sam and Dean do follow the trail and visit Jeffrey in search of the demon. Sam stays to watch a potential victim while Dean goes with Jeffrey. Jeffrey takes Dean to a warehouse and knocks him 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, knocking him to the ground, telling him that he's learned all that the demon needs to teach him and can act on his own now.
Sam and Nora arrive at that point and trick the demon into a devil's trap. Enraged at the demon's actions, Jeffrey charges him with the demon-killing knife while he's vulnerable, forcing Dean to shoot Jeffrey twice in the chest to save Nora's son, killing Jeffrey. The demon is exorcised afterwards, saving Nora's son, but it taunts them that Jeffrey will be "back in black."
|“||There's a sound that comes from their brains, you know that? Only I can hear it. Like a evil little steam whistle.||”|
Jeffrey was an insane, sociopathic individual even before he was possessed; he claimed to be able to hear sounds coming from his (eventual) murder victims. Once he was possessed, the demon worked his way through Jeffrey's list to "motivate" him.
After the demon was exorcised, Jeffrey sought a way to return him, claiming he loved the demon and loved being possessed by him, going so far as to kill the women on his list by himself to get Dean's attention. He also had no qualms in cutting off the ear of a child and sending it to his mother as a threat to her.
- Jeffrey is the first human on the show seen to actually enjoy being possessed by a demon.
- Based on comments made by the demon that previously possessed him, Jeffrey's soul likely goes to Hell and will eventually become a demon himself.
- Jeffrey's desire to be possessed again mirrors Nick's connection to Lucifer in Season 14.