Dalmatian puppies run through the forest.
In the Characters' Past
In 1920s London, a young Cruella De Vil is being mistreated by her mother Madeline as she instructs her Dalmatians to chase her daughter, and is locked in the attic in the same setting that resembles the novel Flowers in the Attic. Fast forward to several years later, and that a reporter, who is revealed to the Author but is using a alias by the name of Issac, is paying a visit to the home pretending to seek out a story after having seen Cruella from the attic, only to have Madeline warning him to stay away. Unfortunately, Isaac returns and helps Cruella escape from the attic. He then takes Cruella out for a date that includes dinner and dancing. Cruella reveals to Isaac that the reason she was kept in the attic was that she witnessed her mother kill her father and her previous husbands; Isaac then reveals to Cruella that he was more than just a reporter and has the ability to use his pen and ink to create magical stories. Isaac proposes that they run away together, and uses his quill and ink to give Cruella her persuasion powers to control animals.
However, for Isaac, his future with Cruella would later take a unique twist that will put his future in danger. When Madeline pays a visit to see him, she tells him that Cruella had lied to him about what actually happened to her husbands: Cruella was the one who killed them, not Madeline, and was trying to prevent her from killing others. When Madeline returns home, Cruella was ready for her, and eventually kills her mother by controlling her Dalmatians and command them to attack her. Afterwards, Isaac realized his quill was missing, so he pays a visit to see Cruella and is stunned that she used him as a means to an end, and Cruella used the skin from her mother's dogs as fur for her signature coat. The confrontation lead the two to fight over the ink, which is then spilled on Cruella, transforming her into the infamous black & white infused-hair character. As Cruella is about to kill him, Issac uses his powers as the Author to make it so that Cruella can never kill anyone ever again by writing it down on a piece of paper.
As Cruella races off into the forest, she is stopped in her tracks by Maleficent, who now knows that she was the one who knew where Lily went after they were sucked into the portal back in the Enchanted Forest. As Maleficent transforms into a dragon, Cruella uses her breath to exhale green smoke and puts her frenemy to sleep, then comes up with a plan to go after the Author. Meanwhile Emma is still arguing with Mary Margaret and David when Regina informs them about Zelena, prompting her to see Belle, who in turn interrupts Gold's plan to make the Author write stories, which in turn prompts Gold to come to the well to see her, and he reveals that his heart is darkening and he will die, only to discover that Belle is being controlled by Regina, who is using it to make sure that Gold does not contact Zelena as Regina schemes to go to New York to confront her half-sister.
Cruella then pays a visit to Isaac to make up for lost time and to offer him a deal, as Gold does not know that they knew each other as Isaac catches on to her deception. And since Isaac knows that Cruella has no power to kill anyone, Cruella, who tells Isaac that she can ways to "Skin a author," finds a way to make it happen by kidnapping Henry by using a controlled Pongo, which she uses to force both Emma and Regina to do her bidding by making the mothers kill Isaac or else Cruella will kill Henry. Unfortunately, as Gold returns to the cabin, he tells Isaac that he knew about his past with Cruella and informs Isaac about the kidnapping, which Gold knows will lead to Emma's darkness. Isaac then hands Gold a note he kept from the club.
At the apartment, Emma, Regina, Hook, Mary Margaret and David discuss their plan of action but even this has Emma concerned. Regina, Emma and Hook searches the woods just in time for Henry to escape from Cruella (while playing Angry Birds), but as the three split up and only Regina and Hook are tricked, its Emma who finds Henry, but Cruella is threatening to throw Henry off of the cliff, then tempts Emma's patience to see if she will do it, reminding her that heroes never kill. At the same time Mary Margaret and David confront Isaac, who reveals that a chapter in Emma's future will involve Cruella and they race to stop her upon reading the note that revealed that Cruella is incapable of killing anyone. Unfortunately, they arrive just in time to see Emma use her powers and kill Cruella by knocking her off the cliff. As a terrified Henry cries in his mother's arms, Emma's face has changed to a sinister look, inferring that her heart is going black.
- Ginnifer Goodwin as Mary Margaret Blanchard
- Jennifer Morrison as Emma Swan
- Lana Parrilla as Regina Mills
- Josh Dallas as David Nolan
- Emilie de Ravin as Belle French
- Colin O'Donoghue as Hook
- Jared S. Gilmore as Henry Mills
- Robert Carlyle as Mr. Gold
- Kristin Bauer van Straten as Maleficent
- Patrick Fischler as Isaac
- Anna Galvin as Madeline
- Victoria Smurfit as Cruella De Vil
- Milli Wilkinson as Young Cruella
- The episode name is a reference to the The Rolling Stones' song "Sympathy for the Devil".
- Milli Wilkinson, who plays the young Cruella, also plays Alice's daughter in the Once Upon a Time in Wonderland series finale "And They Lived...".
- The song that Cruella hears on the radio is a jazz instrumental version of "Cruella De Vil", from the 1961 disney animated movie One Hundred and One Dalmatians.
- Madeline's car is similar in design and color to Cruella's car in 1961 Disney animated movie One Hundred and One Dalmatians.