|Episode(s)||9.04 Slumber Party|
Dorothy is a hunter, and the daughter of American author L. Frank Baum who was one of the Men of Letters. She followed him on one of his trips and got trapped in Oz where she worked with three freedom fighters who were turned into the Tin Man, Cowardly Lion and the Scarecrow against the Wicked Witch of the West. She was killed at some point by the Witch but resurrected and thanks to the Good Witch of the North, was made immune to the Witch's power to kill. At some point she returned to Earth with the head of the Tin Man who had been killed and her father wrote his series of books based on her adventures. After Charlie Bradbury killed the Witch, Dorothy returned to Oz with Charlie to free it. After winning the war for the Emerald City, Dorothy became Oz's new leader alongside the Wizard of Oz who, unknown to her, was evil. After Charlie killed the Wizard, Dorothy once again became safe from threats and Oz was finally, truly free.
In November of 1935, Dorothy arrives at the Men of Letters Bunker seeking help in killing the Wicked Witch of the West who she has captured and has proven immune to everything she has tried. While researching on possible ways to kill the Witch, the Witch frees herself of her bounds and takes possession of Peter Jenkins, who is quickly killed by James Haggerty. The Wicked Witch then gives chase to Dorothy who races to the Bunker's lab where she does a spell to bind herself and the Wicked Witch together and trap them both of in a jar.
Dorothy and the Wicked Witch are released in 2013, when Dean accidentally knocks over the jar, spilling the contents, which creates a web-like cocoon on the wall in the computer room. The Witch frees herself, but Dorothy is left trapped in the web until Dean, Sam and Charlie Bradbury find and release her. Dorothy is horrified as she knows that the Witch is free as well and explains what happened. Sam and Dean have her remain with Charlie to find a way to fight the Witch. Charlie explains to Dorothy what she found: Haggerty worked her disappearance every day until he retired and never gave up and while he couldn't find her, he did figure out how to fight the Witch: poppy extract which he made a deal with a fairy to get. Charlie and Dorothy head to the gun range to make poppy extract bullets as they can stun the Witch.
Meeting with the others, they reveal that they have learned from Crowley that the Witch is looking for a key which Dorothy recognizes as the Key to Oz. Dean found it sometime earlier so he and Charlie go to get it while Dorothy and Sam hunt the Witch. The Witch attacks the two, but Sam drives her off with a poppy bullet. Rushing to find the Witch, they find that she has the key and that Charlie is recovering from apparently being knocked out. As Sam and Dean hunt the Witch, Dorothy stays behind to take care of Charlie.
Talking with Charlie about what happened, Dorothy reveals to Charlie that she was in fact killed by the Witch and that Dorothy had been killed by her too. When Dorothy tells Charlie about her disgust with her father for writing the Oz books which aren't completely true and she believes were his way of dealing with his guilt, Charlie realizes that they were actually clues he was leaving for her on how to deal with the Witch. When Charlie mentions finding "something sharp" to use on the Witch, Dorothy realizes what they need and leads Charlie to the Bunker's garage.
In the garage, Dorothy finds her motorcycle still there even after over 75 years and finds the Ruby slippers which, as sharp magic from Oz, can kill the Wicked Witch. Sam and Dean arrive possessed by the Witch and reveal that instead of the Wicked Witch returning to Oz to rule, she is planning to bring her army to Earth to take over this world. Dorothy tosses Charlie the Slippers and tells her to go after the Witch while she holds off Sam and Dean. Dorothy is quickly overpowered and nearly killed, but Charlie kills the Witch just in time and Dorothy is saved. When a confused Sam and Dean wonder what happened, a proud Dorothy realizes Charlie must've done it.
Later, Dorothy decides to return to Oz to finish the rebellion against the Witch's forces and retrieve her dog and asks Dean to look after her motorcycle, agreeing to his request to drive it. As Dorothy prepares to leave, she offers Charlie the chance to join her, knowing that Charlie wants adventure and will be helpful. After Charlie agrees, Dorothy opens the door to Oz and the two step onto the Yellow Brick Road. Dorothy salutes Sam and Dean before walking off with Charlie.
After returning to Earth, Charlie reveals that she and Dorothy fought a war for the Emerald City and were losing so Charlie made a deal with the Wizard of Oz to split herself into her good and dark sides. Her dark side single-handedly won the war and Dorothy and the Wizard became the new leaders of Oz. Unknown to Dorothy and Charlie, the Wizard was evil and using Dorothy and her rebellion to gain power. After returning to Earth to stop her dark side, Charlie learned the truth from Clive Dillon who was the Wizard's own good side. Clive mortally wounded himself to summon the Wizard to Earth and then Charlie killed them both, saving Dorothy from him unknown to her. After the two Charlie's were reunited, Charlie was unable to return to Oz and Dorothy due to Dark Charlie breaking the Key to Oz, however, she was content in the knowledge that Dorothy was safe once more.
- Dorothy appears to be in her 20s in 1935, however The Wonderful Wizard of Oz was published May 17, 1900. According to writer Robbie Thompson, the reason for this discrepancy in age was to be explained with a line of dialogue detailing that time moves differently in Oz, however the line ended up getting cut from the episode. The line was eventually used by Charlie in 10.11 There's No Place Like Home.