|Status||Deceased (killed by Sam)|
|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. Benovent Convent which involved the Knight of Hell Abaddon and a few demons. Although initially successful in casting out some of the demons, Henry and Josie later proved to be incapable of defeating the Knight. 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. From then on, it was unknown whether she was aware of Abaddon's actions, including the murder of the Men of Letters.
Using her, Abaddon chased after Henry, although he managed to escape with the secret key to the Men of Letters' headquarters. Abaddon continued to use her body and Josie had to suffer being cut up into pieces for Abaddon to be stopped.
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. 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.
The body of Josie Sands was restored by a ritual. 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.
- 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.