Before First Curse
Robert gets married to Ruth, with whom he has twin sons, named David and James. However, their livelihood on the farm is crushed by poverty. A wizard named Rumplestiltskin offers them a large amount of money for one of their sons, who will be given to a barren king and queen. To save themselves from their destitute situation, Ruth and her husband give up James.
As they raise David, the couple constantly quarrel about Robert's drinking problems. Despite his apparent dependency on alcohol, the man is genuine about changing for the better. He promises that, when he returns from a two week journey to bring supplies onto their farm, his addiction will be gone. As the man leaves for his trip, David wraps a coin as a good-luck charm around his father's wrist. On the fourteenth day, Ruth and David receive word that Robert died after he got drunk at a tavern and fell into a ravine on his journey home.
Years later, David shares his father's history with his new friend Joan.
Eventually, James dies and Rumplestiltskin persuades David to replace his twin. Surprised to learn he had a brother, the shepherd is told by his mother that his father regretted giving the baby up immediately after the decision was made and took it to his grave.
After First Curse
When David confronts Regina about the fate of Emma Swan and Mary Margaret, his family who just fell through a portal to the Enchanted Forest, the mayor feigns ignorance and mocks David for posing as a prince while he is nothing more than the son of a shepherd.
Before Third Curse
In Camelot, David confides in King Arthur his old dreams of changing the world, to which he was led by the will of being different from his father, who drank his life away, and brother, who accomplished nothing but evil.
After Third Curse
Having retrieved from Rumplestiltskin the coin David once had given his father, the Evil Queen meets with David about it. David claims he's made peace with his father's death. But Regina's evil half suggests that what happened might have not been an accident. Making a deal with Mr. Gold, Rumplestiltskin's cursed persona, David delivers a tape to Belle and gains information about the true nature of his father's death. He later shares this revelation with Snow White. The man did not die in an accident, but, rather, was stabbed by an unknown person. He contemplates that the killer is out there somewhere, but Snow encourages her husband to leave the past behind by accepting that his father at least kept his vow to not drink again. David agrees not to seek vengeance, but he ultimately changes his mind and keeps the information, unbeknownst to Snow.
Celebrating Emma surviving her battle with Gideon, David is haunted by his father's ghost who urges that he must know the truth. With Hook and August's help, David delves into what really happened all those years ago and discovers his father never went on a supply run as he said. He instead went out to find James, who was trying to escape the miserable royal life he was adopted into, and reunite his broken family. Robert tracked his young son to Pleasure Island and was sober throughout his journey, despite the place's temptations. Having a good hunch of the killer's identity and knowing his location, David heads to the hospital after restraining an interfering Hook. At the asylum, he confronts Albert Spencer, the cursed and incarcerated counterpart of King George. Spencer reveals that Robert had been offered a great reward for finding James, but he refused and was sentenced to death while making it look like an accident. He smugly infers that the shepherd had great prospects for his family if he had succeeded, only to believed to have died a drunken failure. Enraged, David tosses a knife at the wretched man's feet and tries to kill him to avenge his father. Fortunately, Hook arrives before he can slit the corrupt despot's neck, re-imprisoning him. He eases David's bloodlust and fears of losing his family by reminding him of his father's honorable actions. Finally able to make peace and move on with a newfound respect for his father, David throws the coin into the harbor and Robert's pleased spirit departs.
However, Hook realises, from the story pages August retrieved, that he really killed Robert. This discovery troubles him, as he intends to propose to Emma, Robert's granddaughter. He tries to bury his action, but Emma catches him in the act. She's hurt that he tried to hid the incident. He thinks about leaving with his old friend, Captain Nemo, but changes his mind. However, Gideon traps him aboard and makes the Nautilus set sail so he can't help Emma. Eventually making it back to Storybrooke, Hook apologises to Emma for not admitting his murder of her grandfather sooner. After waking David and Snow, he does the same with the former. David forgives him, knowing Hook was different person back then and has changed since.
- "The Shepherd" (First mentioned)
- "Broken" (Mentioned only)
- "White Out" (Mentioned only)
- "Siege Perilous" (Mentioned only)
- "A Bitter Draught" (Mentioned only)
- "The Other Shoe" (Mentioned only)
- "Murder Most Foul" (First appearance)
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