|“||Seriously, I'm proud of you. And you're gonna knock em dead on Monday; you're gonna get that full ride. I know it.||”|
Little is known about Jessica's past or where she came from. She was likely a college student when Sam's best friend Brady introduced them. Neither were aware that Brady was actually possessed by a demon and was putting them together for Azazel's purposes. A year and a half before the pilot episode of the series, Jessica and Sam Winchester became a couple and began living together.Despite loving each other deeply, Jessica never got to know about Sam's family secrets, or that Sam had been dreaming about her death prior. When Dean Winchester, Sam's older brother, visited to bring Sam along to look for their father, Jessica worried that Sam would lose his chance in university by following his brother, but Sam reassured her that he would be back before Monday.
During the end of the weekend, Jessica made cookies as a welcome present for Sam, before she was killed in the same way that Mary Winchester was killed; sliced across the stomach on the ceiling. When Sam saw Jessica, she seemed to still be alive, but soon burst into flames. The Winchesters believed that the demon that killed their mother, Azazel, did it, but Brady later told them it was him on Azazel's orders in order to push Sam back into hunting.
Jessica's death is what makes Sam go back to the hunting life in order to find Azazel and avenge her death. She is often the topic of choice whenever Sam is feeling down or becomes attracted to another woman in the first two seasons. Weeks after her death, Sam has nightmares about her all the time, making him sleep as little as possible. In "Home", Sam reveals to Dean that he had visions of Jessica's death before it happened, blaming himself for not telling her or doing something about it. This is also the secret that he used to summon Bloody Mary in the episode "Bloody Mary". After this episode, though, Sam's nightmare seems to dim, and he is finally able to move on with his life in the episode "Heart".
In Dean's wish-world in "What Is And What Should Never Be", Jessica is still alive, and she and Sam are engaged. This is followed up with the fact that, in "Devil's Trap", Azazel mentions to Dean that Sam was shopping for engagement rings and intended to marry Jessica before Dean came to visit him.
In "Free to Be You and Me", Lucifer communicates in Sam's dreams through an illusion of Jessica, telling him how he cannot run from who he is and that it was that which got her killed. Eventually, however, Lucifer ceases this form and changes back to Nick's shape.
In "The Devil You Know", Dean captures a powerful demon going by the name Brady while searching for Pestilence. The demon is revealed to be possessing Sam's best friend from Stanford, having taken possession of Brady to get close to Sam. Sam realizes that Brady is Jess' true killer and not Azazel as was previously believed. Brady confirms this, telling Sam he brought him and Jess together and then killed her on Azazel's orders to push him back into hunting as the demons needed him hunting monsters. Sam nearly kills Brady for Jess' murder, but ultimately relents as they need the information he has. After getting the information needed, Sam kills Brady with Ruby's demon-killing knife and finally avenges Jess' death.
Jessica was a cheerful and optimistic woman who encouraged Sam to do good academically. She also had a sense of humor, telling Sam that without her, he would "crash and burn". Jessica loved Sam dearly and often expressed concern for his well-being, his happiness, and his future.
When Sam left to join Dean in what was supposed to be a temporary trip, Jessica expressed sadness due to her concern, which was made worse since Sam did not reveal to her the truth behind Dean's hunting. Jessica mentioned how she wanted to know more about Sam's past, and while she was generally okay with not knowing much about it, she was visibly unhappy at Sam's seemingly lack of trust.
Nevertheless, in her final moments, Jessica was eager and ready to welcome Sam back home, baking him cookies while she waited. In her final hour, Jessica gazed upon Sam from the ceiling, watching him as he returned home clueless about what had happened to her until he felt her blood drip onto him. Jessica was visibly in pain until she burst into flames, never to know that her relationship with Sam was doomed from the beginning.
Physical Appearance Edit
Jessica was a blonde woman of average height. Her hair reached her mid-back and was sometimes kept in curls. She is never shown tying it up, always let loose. In one of her first appearances, Jessica wore a nurse outfit for Halloween and was later shown in her pajamas, consisting of a gray shirt and blue shorts. After her death, Jessica always appeared in her white night gown, the dress she died in. The only exception is her counterpart in Dean's dream caused by the djinn. This version of Jessica also wore an engagement ring, something Sam never managed to give to the real Jessica.
- Season 5
- Season 12
- Jessica seemed to be a student at Stanford like Sam, but it is not known what she was studying.
- Jessica shares her birthday, January 24, 1984, with Dean. In an interview, Eric Kripke said that January 24 is his wife's birthday, and "It's kinda my Valentine".
- The studio bosses wanted Kripke to write Jessica as an ongoing character, but Kripke thought it would not work and suggested killing her off, which they liked. The studio then urged Kripke to make Jessica an evil demon character who was planted into Sam's life with purpose, and whose betrayal drives him on the road as he realizes demons are closer to him than he thought. This was used in Season 5 with Brady and Lucifer's revelation of people he knew in his childhood being affiliated with demons.
- Jessica has a slightly larger role in the Anime series, though her fate remains unchanged. She is also said to be a law school student.
- Jessica's line of 'crash and burn' is ironic, as she was burned alive.
- Both Mary and Jess' deaths were similar: they were both wearing a white nightgown; Sam was lying underneath them as they died; both were killed in the same manner; they both wore white nightgowns at the time of their death; and Prince of Hell Azazel influenced both deaths.