Will and his younger sister, Penelope, grow up close, but after she dies from drowning, he is unable to move on from her death. On the outskirts of the Emerald City of Oz, he ends up restrained by a guard, who is knocked out once a portal door lands on him. From the door, Robin Hood steps out and frees Will. Robin Hood explains his intentions of stealing an elixir of the wounded heart from the Wicked Witch, which he needs to secure his as well as his wife's future. Wishing to use the elixir to alleviate his heartbreak over Penelope's death, Will asks Robin Hood to fetch him some in exchange for not telling the guard about him breaking into the Emerald Palace. Since Robin Hood also requires a disguise to get into the Emerald Palace, Will helps strip the uniform from the unconscious guard. Later, Robin Hood returns, having only gotten one vial of elixir, but he lies about not acquiring any of it. Believing he failed in his mission, Will praises his courage for making the effort and assures him that his wife will understand even if he didn't succeed. Akin to Robin Hood and his wife, he relates how his own sister was once the person who understood him best, but that ended when she died. Realizing Will needs the elixir more than him, Robin Hood hugs him in farewell and secretly slips the vial in the latter's pocket. Only after Robin Hood has left through the portal, Will finds the elixir, much to his surprise. ("Heart of Gold")
In the Enchanted Forest, Will and his love, Anastasia, want to find a way to another world. After helping Robin Hood's band of Merry Men steal riches from a wealthy man on the road, he is accepted into the group. He suggests the next looting location in Maleficent's castle, which has enough gold to feed the entire kingdom. Robin Hood refuses, but is tempted into accepting due to the gold they will receive to help the poor as well as Maleficent's current absence from the castle. With the plan is set into motion, Will rushes back home to Anastasia to inform her everything went smoothly and they will be getting what they need from the castle. At some point before or after this, Will meets Robin Hood's love, Maid Marian. He inquiries why she gave up everything to be with Robin Hood, and Marian states her belief in the good in his heart and that true love is worth fighting for. In the castle, although Robin Hood warns they'll only take the gold, Will secretly takes a looking glass. After the gold is procured, the Merry Men celebrate at camp, but Maleficent's voice demands they return a stolen item or face the consequences. Robin Hood calls the culprit out, but Will guiltily remains silent. At night, he tries slipping away when Robin Hood confronts him about his theft. Robin Hood allows him to go as he believes the worst punishment for Will's actions will come in the near future. Returning home, Will and Anastasia open a portal with the looking glass. On Anastasia's decision to go to Wonderland, they prepare to jump in. ("Forget Me Not", "The Snow Queen")
Seconds later, their leave is delayed by Anastasia's mother, who is strongly against her daughter throwing away a life of privilege for Will, a noted thief, and choosing him as her partner. Knave interjects to say he's not a thief anymore. To her mother, Anastasia is a failure and states if she were to come home, it'd be by taking on cleaning of the chamber pots. Will comforts a hurt Anastasia and affirms he will build a life for the both of them because of his love for her, and not because he wishes her to be different. Anastasia promptly leaves with him into the portal to Wonderland, but they end up poor and scourging for berries. A wagon passes on the road with an abundance of fresh baked goods for the royal ball, to which they both attend by stealing clothes and forging invitations into the castle. Will steals food, hiding it in his clothes, when he is thrown out by the guards for a forged invitation, as Anastasia is hauled out as well for wearing a stolen gown. Some time passes, and they are at another pitfall. Will is uneasy at Anastasia's suggestion that they steal the castle's crown jewels, but she insists they are poor and need the money. Anastasia intends to grab the jewels and drop them down to him, and then they will return home via the looking glass to sell the goods. Later, while Will is waiting for her to finish nabbing the jewels, he sees the Red King announce his new Queen. Stunned, he watches as Anastasia herself, garbed in fine clothes and a red crown, walks onto the balcony to greet the public. Will briefly catches her eye, but then she pretends not to see him. ("Heart of Stone")
The night prior to royal wedding ceremony, he hops into the castle from the balcony to get answers from Anastasia for her previous actions. Though he has hopes it's a con to gain the throne and riches before she leaves for home with him, Anastasia claims to be doing what is best for him as well as herself. While reminding her of all the good times they had together, the guards burst in to apprehend him. Before escaping down the balcony, Will requests Anastasia to come to their old wagon and run away with him. The next morning, instead of Anastasia, the Queen of Hearts shows up at the wagon to inform him that his former flame will not be arriving. Crushed, Will asks her to take out his heart, desperate to alleviate the heartache, even though he won't ever be able to love again. After the request is fulfilled, he leaves the wagon with his belongings as she pockets his heart. ("Heart of the Matter")
Soon after, Will begins working in service to the Queen of Hearts as the Knave of Hearts. He has little choice in disobeying her since she possesses his heart and thus has full command over him. Out on patrol in the woods, he and the other soldiers are hunting down the "most dangerous criminal in Wonderland". As Knave is chasing the suspect, he is caught at sword-point. The criminal turns out to be a young girl, Alice, though she claims the wanted charges against her are false. He lets her walk away, but promises they will meet again. Knave tracks her down, but lands into Alice's net trap. Alice insists that her only offense is attempted thievery of a weeping willow flower from the Queen of Hearts' garden, which he believes. However, due to the Queen's control on his heart, he still wants to kill her. When he admits his lack of free-will, Alice goes to steal his heart from the Queen's vault and later uses it to command him to stop trying to harm her. As a favor, Knave agrees to help her find proof of Wonderland and they have a drinking contest at a tavern. Their friendship deepens when he tells her about his sister, Penelope, who died young. Feeling guilty about using him, Alice returns his heart; deciding to find proof alone. Knave accepts her decision, but he helps anyway and procures the White Rabbit for her. In the Queen's maze, he stays behind to distract incoming guards while Alice flees, home-bound, with the White Rabbit in a bag. ("To Catch a Thief")
Despite regaining his heart, Knave cannot bring himself to put it back in as he fears re-experiencing the pain of Anastasia's betrayal. Now freed from the Queen of Hearts, he befriends a homeless girl named Elizabeth and shelters her from the streets. They find work under the Caterpillar as his Collectors. Will eventually trusts her enough to open up about Anastasia, and Elizabeth secretly falls in love with him. Over the course of his employment, Will accumulates many monetary debts that he owes the Caterpillar, which are not repaid. ("The Serpent", "Nothing to Fear")
When the Evil Queen of the Enchanted Forest casts a curse, Will is engulfed by it and taken away to another realm.