|Status||Deceased (killed by Dean)|
|Occupation||Man of Letters (former Initiate)|
|Affiliation:||Men of Letters (formerly)|
|Portrayed by:||Alaina Huffman|
Josie was an initiate for the Men of Letters. She worked closely with Henry Winchester, even up to their final test prior to their initiation to become full-fledged Men of Letters. In 1958, they investigated events in St. Bonaventure Convent which involved the Knight of Hell Abaddon and a few demons. Although they managed to exorcise two of the demons, Henry and Josie later proved to be incapable of defeating the Knight as Abaddon was immune to exorcisms. As Abaddon stated her intent to possess Henry to study and destroy the Men of Letters, Josie offered herself instead. Abaddon claimed this was because Josie loved Henry. The Knight mocked Josie, claiming that Henry loved her as well, but only as a sister. Soon after, Josie was possessed by Abaddon. Abaddon then used Josie to successfully infiltrate and destroy the Men of Letters.
After slaughtering the Men of Letters, using Josie's initation to get close to the elders, Abaddon, still possessing Josie, followed Henry through time to 2013 where she was promptly stabbed by Dean with the Demon-killing knife. However, Abaddon survived and continued her pursuit of the Winchesters. At one point, she abandoned Josie for Larry Ganem's wife, but returned to Josie's body after killing the Ganems and capturing Sam. Henry and Dean lured Abaddon into a trap where Henry shot a devil's trap bullet into her head, trapping Abaddon in Josie's body as they couldn't kill her and then cut her up into pieces and buried them separately.
Later, while searching through the Men of Letters' archives, Sam and Dean found a film made by Josie for the order, chronicling the efforts by two priests, Father Max Thompson and Father Simon to cure a demon. The effort failed, but Max Thompson eventually succeeded in completing the ritual.
Deciding to use Abaddon to complete the third trial, Sam and Dean put her and thus Josie back together, keeping her hands off for safety. The Knight of Hell then revealed she learned about Josie and the Men of Letters from Thompson himself, moments before his death and used Josie as a result to seek out and kill the Men of Letters. However, before Sam and Dean could cure Abaddon, she managed to control Josie's hands to reach into her mouth and pull out the devil's trap bullet they had used to trap her, allowing Abaddon to escape.
Despite being set on fire, Josie didn't burn to ash, allowing a demon to recover her charred remains and perform a ritual to restore her. This allowed Abaddon to resume her possession of Josie. Whether or not Josie herself was still alive is unknown, although it is highly unlikely, as demons do not require the consent of their human hosts and could even possess a corpse for years. Abaddon then proceeded to use Josie as her continuous vessel during her crusade to takeover Hell. If she was resurrected, she is killed again and for good when Dean kills Abaddon with The First Blade while she is still possessing Josie's body. Dean then stabs Abaddon (and thus Josie) several more times even after they are dead under the Mark of Cain's influence.
- As Henry apologized to Josie after discussing something about having a family and the risk they were exposed to, it is possible that Josie was an orphan or was the only surviving member of her family.
- Despite knowing that Henry was married Josie was in love with Henry even though he didn't share the same feelings, even allowing Abaddon to possess her and put the other Men of Letters at risk.
- Unlike other demons, Abaddon showed a fondness for using Josie as her vessel, restoring her to act as her vessel once more after her body was destroyed by Holy Fire and using a different demon to do it rather than possessing someone else to do it herself. She indicated that like Dean, Josie was "worthy" of being possessed by her. Abaddon was the only demon that showed this kind of attachment to a vessel: Ruby, Meg and Crowley had a preferred vessel too but unlike Abaddon and Josie, they never restored the vessel after it was destroyed.
- It's unclear if Josie was actually alive or not in season 9: demons can possess corpses so Abaddon may have just restored her body and not her life. However, it wasn't made clear one way or the other.
- Josie may have actually been dead before Abaddon abandoned her body due to Holy Fire: Dean stabbed her with the Demon-killing knife and though it didn't kill Abaddon, she did leave Josie's body for Larry Ganem's wife for a brief time and as shown with Meg, the wounds demon vessels receive return when the demon possessing them is exorcised or leaves. However, Crowley appears to be able to heal his vessel's wounds completely and Abaddon is more powerful so it is unclear.
- Season 8
- Season 9