Dark One Deals

Throughout the realms, Rumplestiltskin became known as a being of great power and fear, able to grant a person's deepest wishes and darkest desires with Magical Deals that proved to be worse than he would initially proclaim. These deals appear to transcend into the Storybrooke reality as well, with Rumplestiltskin's counterpart Mr. Gold retaining a similar disposition for swindling people in desperate situations. In either reality, it appears that Rumplestiltskin always benefits in the long term through his deals, despite short term set-backs brought about by certain individuals. He has only broken one deal as Rumplestiltskin, a second deal as Mr. Gold, and a third deal, that was considered invalid.

Fairytale Deals

Baelfire's Happiness in Exchange for his Powers

Baelfire is unhappy with the Dark One for a father. Rumplestiltskin murders villagers, which scares Baelfire and leads to his estrangement from most of the other children. Rumplestiltskin explains that the only way for him to give up his powers is to be killed with the Dark One's dagger. He and Baelfire make a deal that if Baelfire can find a way for Rumplestiltskin to safely give up his powers, he will do it. Baelfire meets with the Blue Fairy and she gives him a magic bean which will take them to a world without magic. Baelfire takes his father into the woods and throws the bean on the ground. A portal opens up and Baelfire starts to enter; however, Rumplestiltskin cannot bring himself to do so. Baelfire calls his father a coward before he falls into the portal. Rumplestiltskin is upset afterwards and regrets this decision with all his heart. (Note: This is the first deal Rumplestiltskin has broken). ("The Stranger")

The Magic Bean in Exchange for William Smee's Youth

While sitting at a table in a tavern, Rumplestiltskin is approached by a man who introduces himself as William Smee. He, after hearing of Rumplestiltskin's power, backstory and reputation, offered him a magic bean that has the ability to travel between worlds. When Rumplestiltskin replied he had been told they no longer existed in this land, Smee replied that this bean was from another. Rumplestiltskin immediately asked what Smee wanted in return. When Smee said he wanted eternal life, Rumplestiltskin replied that it was not possible. However, he can make Smee's "clock" go in reverse back to his youth, giving him extra years. However, Rumplestiltskin threatened that if Smee tricked him, he would make the "clock" go forward, turning him to dust. This deal is later considered invalid due to Smee being kidnapped by Captain Hook and Milah's crew and having the bean taken from him. ("The Crocodile")

The Magic Bean in Exchange for Milah and Killian Jones's Life

When the supposedly dead Milah arrived before Rumplestiltskin ripped Captain Hook's heart out, she revealed that she had taken Smee and his magical bean captive. When Rumplestiltskin asked what she wanted, she asked to exchange the bean for her and Killian's life. The next day, when Rumplestiltskin went to their ship to collect, he told her that although he understood why she left him, he asked why she ever left their son. She said that she let her misery cloud her judgment. Rumplestiltskin asked why she was so miserable, to which she finally admitted that she never loved him. Angered by this, Rumplestiltskin ripped her heart out and killed her by crushing it into dust after Milah admitted her love for Killian. Enraged, Killian drove a hook into Rumplestiltskin, but to no effect. Rumplestiltskin said that despite this, he would not kill him, wanting him to suffer as he had. Instead Rumplestiltskin severs the hand holding the magic bean that Killian was holding. It is later revealed that the hand that Rumplestiltskin cut out did not hold the bean, and he had been deceived. (Note: Rumplestiltskin didn't break this deal because he killed Milah, so he didn't receive the Magic Bean). ("The Crocodile")

Marionette Potion in Exchange for its Victims

Rumplestiltskin had a business relationship with Jiminy Cricket, who would bring him possessions stolen by his parents during their travels as puppeteers in exchange for Rumplestiltskin's gold thread. One day, sensing that Jiminy had become disillusioned with being forced into a life of deceit and thievery, Rumplestiltskin offered him the chance to escape by giving him a magic potion that would take care of his parents for good. In return, Rumplestiltskin only asked that he be given Jiminy's parents after they had taken the potion, as it would count as his fee. However, Jiminy's plan backfired when his parents switched Rumplestiltskin's potion with a bottle of rainwater they had planned to give to another swindled couple. After learning that the couple had been turned into marionettes through the potion, Jiminy left his parents and made another deal with the Blue Fairy to become a cricket in order to mentor the couple's now orphaned son, Geppetto. Meanwhile, Rumplestiltskin, true to his word, took possession of the marionettes, who were later shown to be owned by Mr. Gold in his pawn shop in Storybrooke. ("That Still Small Voice")

Teaching Queen Regina Magic in Exchange for an Unspoken Action from Her

Rumplestiltskin first encountered Regina when she was desperately trying to escape from her mother's clutch. He gave Regina the Looking Glass which she later pushed Cora into (with a little of his "encouragement"). Shortly after, Regina meets up with Rumplestiltskin and gives him back the book that her mother stole from him. She then tells him that she cannot use magic because of how much she loved it. Rumplestiltskin says he could teach her many things. Regina agrees, telling him that she will not turn out like her mother. In exchange, he only states that someday she will do a favor for him. ("We Are Both")

An Enchanted Heart in Exchange for Queen Regina's Heartbreak

When Victor Frankenstein is about to return to his realm, he asked if his end of the deal is complete. The Mad Hatter replied that the deal is only complete when "he", Rumplestiltskin, said so. It is revealed that Victor didn't try to bring back Daniel at all, as the enchanted heart he supposedly used was still intact and was intended to be used on Victor's brother. When Victor asked if Rumplestiltskin was satisfied with the result, Rumplestiltskin replied that Regina did seem heartbroken and used magic for evil for the first time. ("The Doctor")

Prince Charming in Exchange for the Location of a Fairy Godmother

King George was childless and wanted a son. Rumplestiltskin gave King George a peasant infant to raise as his son in exchange for an unidentified "pittance". Many years later, the son is killed in a duel, after he had agreed to slay a dragon in the kingdom of Midas in return for gold that George's kingdom desperately needs. When King George asks Rumplestiltskin for help, Rumplestiltskin brings him the son's twin brother in exchange for the location of a Fairy Godmother, elaborating that her death in "The Price of Gold" happened as a result of this particular deal. Later, the twin brother takes on the identity of his slain brother: Prince James. ("The Shepherd")

Protection from the Ogres in Exchange for Belle

Rumplestiltskin made a deal with Belle that she should forever be caretaker of his estate in return for protecting her father's kingdom from the ogres. Through her stay in his castle, Belle learned that Rumplestiltskin had once had a son who shared his kingdom, but now had left him all alone, causing him to seek company which Belle could provide. Rumplestiltskin later broke this deal himself, releasing Belle from their arrangement after suspecting that she was in league with the Evil Queen planning usurp his power. This assumption turned out to be false. The Evil Queen had manipulated Belle into kissing Rumplestiltskin and having him be cured of his evil by the magic of true love, a spell which Rumplestiltskin resisted, believing himself to be unlovable, and still needing his magic in order to find his long-lost son. ("Skin Deep")

The Story about How Rumplestiltskin's Son left him in Exchange for Belle coming Back with Straw

Rumplestiltskin didn't want to talk about Baelfire, and he was starting to feel something for Belle, so he set her free, and said that if she came back then he would tell her Baelfire's story. He didn't expect Belle to come back, but when he noticed she came back because of the Evil Queen, he got mad and tell her she had to leave. It was later, in Storybrooke's Library that Mr. Gold completed his part of the deal by telling Belle the story he'd promised. ("Skin Deep")("The Crocodile")

Potion of Forgetfulness in Exchange for a Lock of Snow White's Hair

Rumplestiltskin made a deal with Snow White in exchange for a potion which would allow her to forget her memories of Prince Charming so that he would be able to fulfill his responsibilities to his father's kingdom. Rumplestiltskin only asked for a lock of Snow White's hair in return, which he later used to bottle "true love" by placing it in a bottle with Prince Charming's hair. ("7:15 A.M.")

Snow White's Location in Exchange for Prince Charming's Cloak

Prince Charming demands Rumplestiltskin tell him where Snow White is upon learning of Snow White bloodthirsty acts against the Queen. He agrees, but only if he will give him his cloak, claiming it is drafty in his castle. Prince Charming takes off his cloak and Rumplestiltskin show him a map of where Snow White is. Prince Charming leaves and Rumplestiltskin picks up the cloak, smells it then leaves. He later pulls hair from the cloak and puts it in a bottle with Snow White White's hair to form a true love potion. ("Heart of Darkness")

Hiding A Bottle of True Love in Exchange for An Enchanted Ring

Prince Charming escapes imprisonment in the Evil Queen's castle, but finds himself lost in the Infinite Forest. Rumplestiltskin comes making an offer to him that will help him get to Snow White. He took Prince Charming's mother's ring and enchanted it so that closer he is to Snow White, the brighter it will glow. He won't give it to Prince Charming without a price. Prince Charming must take Rumplestiltskin's bottle of true love, which was enclosed in a golden egg, and hide it in the belly of a beast. Prince Charming takes the egg and fights a witch named Maleficent, who shape shifts into a dragon. He is able to throw the egg into her body just behind the flap of her ear before he makes his getaway from the beast. Satisfied with the terms of the deal meant, Rumplestiltskin gives Prince Charming the enchanted ring, and even sets him up in princely clothes as he rides off on horseback to find Snow White. ("A Land Without Magic")

Cinderella's Night at the Ball in Exchange for her Firstborn

Rumplestiltskin destroys Cinderella's Fairy Godmother just after she appears to soon-to-be-princess, stealing the Fairy Godmother's wand in turn. In exchange for something "precious" to Cinderella—which turned out to be her firstborn child—he uses the wand to bless her with a magical night at Prince Thomas' ball. He returns to claim his prize from the regretful pregnant Cinderella. ("The Price of Gold")

Information About the Curse in Exchange for the Name of Snow White's unborn Child

Snow White and Prince Charming come to Rumplestiltskin to get information about the curse. He tells them that they have to get their child to safety and that it will return on its 28th birthday. In exchange, Snow White tells him that the name of her unborn child is Emma. ("Pilot")

Information about How to Cast the Dark Curse in Exchange for Riches, Comfort and Obedience

In exchange for the secret to completing the Evil Queen's Dark Curse, Rumplestiltskin demanded riches and comfort in the world without magic the curse would take them to, and that the Evil Queen has to give him anything he asks for as long as he says "please". ("The Thing You Love Most")

Storybrooke Deals

Ashley's Child in Exchange for a Large Sum of Money

Mitchell Herman arranged for Ashley Boyd's child to be taken by Mr. Gold for a large sum on money. Mr. Gold eventually broke this deal as part of a new deal with Emma.

Ashley's Release from Her Deal in Exchange for a Favor from Emma

In Storybrooke, when Ashley Boyd's first child was about to be born, Mr. Gold returned to claim his payment. Ashley is discouraged by all the citizens of Storybrooke that she can't raise her child alone as she is too young and is not ready. Her boyfriend, Sean Herman, who fathered the child, is forbidden by his father to see her. She refuses to give up the child and is determined to change her life to keep her child, under the influence of Emma Swan. Ashley gives birth to her daughter, Alexandra, and Emma makes a new deal with Mr. Gold that if Ashley got to keep her baby, Emma would owe him a favor, but we do not know what it is yet. After Emma has made the deal, Sean returns to Ashley to help take care of the baby, symbolizing that Rumplestiltskin's deal has been honored by the bail bondsman, Emma Swan. While being held in prison, Mr. Gold is still very aware of the deal they made, and tells Emma that he will ask for something important when the time comes. ("The Price of Gold")

Emma Swan's Allegiance After Being Elected Sheriff of Storybrooke

During Storybrooke's election for a new sheriff, Mr. Gold approached Emma Swan with a proposal for political support and financial backing during her campaign. Emma, angered by Regina's constant attempts at trying to force her out of town, tentatively accepted Gold's deal, believing him to be the lesser of two evils. However, after learning that Gold staged a firebombing in the Storybrooke city hall in order to paint Emma as a selfless hero, Emma turned on him during a public debate with Sydney Glass, thus nullifying their arrangement. However, it is learned after Emma is elected that Gold had always planned for her to betray him, realizing that standing up to him publicly was a greater feat than standing up to Regina as it painted her as being brave and selfless. Either way, Gold reminded Emma that she still owed him his favor from the episode "The Price of Gold", and thus, actually had no choice in the matter when it came to bargaining her allegiance, as it was something Gold already owned. ("Desperate Souls")

A Plot of Land in Storybrooke's Forest for Fifty-Thousand Dollars

After negotiating with Regina for the land necessary to construct a children's playground, Mr. Gold sells her a small plot in Storybrooke's forest, stating that he owns a sizable amount of acreage surrounding the town. At the time, Emma Swan and Sydney Glass suspected Gold's payment was embezzled from the town by Regina so that she could construct a second home, but it turns out the whole deal was a ruse so that Regina would be able to deflect public suspicion from her shadier actions and have a legitimate reason to keep Henry from spending time with Emma. Wanting to keep his business transactions private, Gold never asked what Regina wanted the land for, but probably suspected her intentions nonetheless. ("Desperate Souls")

Monetary Loan For Moe French

On the day before St. Valentine's Day, Mr. Gold sought to collect on a loan for an undetermined amount of money that he had given to Moe French in order to support his fledgling florist business. Knowing that French didn't have the liquid capital necessary to pay back the loan on time, Gold repossessed French's delivery van with over $1000 of fresh-cut roses in the back. After ignoring French's pleas that this was no way to do business, Gold warned him not to make such bad business decisions in the future. ("Skin Deep")

Mr. Gold's True Name in Exchange for a Chipped Teacup

After being arrested and held by Emma Swan for assaulting Moe French, Mr. Gold bargained with a visiting Regina for the possession of an item Regina procured in an burglary carried out by Moe under Regina's manipulations. As such, Regina agreed to would give back what she took in exchange for Gold's true name. Admitting defeat, Gold tells her his name is Rumplestiltskin, revealing that he remembers everything from his previous life. Regina then gives back the teacup that Belle chipped, Rumplestiltskin's only memento of Belle. After this exchange, Gold tells Regina that this changes nothing as he still has more power than she does in Storybrooke. Although this is true, it is revealed that Regina is holding Belle's Storybrooke counterpart hostage in what appears to be the mental ward of Storybrooke's hospital. ("Skin Deep")

Being Mary Margaret's Lawyer due to being "Invested" in her Future

After Regina frames Mary Margaret for Kathryn's murder, Mr. Gold offers his services as a lawyer to help out. When questioned why he was helping without asking for anything in return, he said he was invested in her future, something his counterpart Rumplestiltskin said to Snow White White previously. ("Heart of Darkness")

Assisting in Revealing that Regina Framed Mary Margaret

At wits end with how Regina has always countered her except for the Sheriff election, Emma asked Mr. Gold for help. When asked if she was willing to go as far as it takes to prove Regina to be corrupt, Emma answered that she was willing to go even farther. Mr. Gold agreed to help, saying that Emma is powerful in her own way. ("Heart of Darkness")

Helping Regina Make Mary Margaret Look Guilty in Exchange for Her to Convince the Jury to Drop the Charge of Moe French's Case

This deal was made by Regina out of desperation to have revenge on Snow White for giving away her secret back in Fairytale Land. Though it was successful at first, Mary Margaret was convinced to return to her cell by Emma. Mr. Gold told Regina that she still could get her revenge, it was only a matter of time. It is revealed in The Stable Boy that Mr. Gold asked for Regina's help to get the charges against him dropped to which he offers a plan to frame Mary Margaret. ("Heart of Darkness")

A Person-Finding Potion and No Interference in Exchange for "Peace"

This deal was made by David Nolan in order to find The Mad Hatter in order to fix his hat to travel to Fairytale Land. In exchange, Mr. Gold asked David to leave him alone. He agreed with the condition that they would both stay out of each other's way. ("We Are Both")

Cora's Old Spell Book in Exchange for Regina's Silence about Fairytale Land's Existence

When Gold found Regina in his shop, he asked her to leave by saying "Please". After discovering his words had no power anymore, Regina threatened to expose the existence of the Enchanted Kingdom, namely that it still exists. In return for her silence, she asks for her mother's old spell book, the one that was given to her by Rumplestiltskin. He reluctantly agrees, but as she was leaving the shop he commented that he was wrong when he first thought that Regina didn't look like her mother, feeding Regina's fears. Regina later broke this deal when she told David that the Enchanted Forest still existed, though Mr. Gold did not take back the book. ("We Are Both")

Dr. Whale's Arm Reattached in Exchange for Dr. Whale Saying "I Need Magic."

When Dr. Whale resurrected Daniel as a monster, he ripped Dr. Whale's left arm off. Regina goes looking for Dr. Whale after seeing Daniel in the streets and finds him in his operating room. She finds Whale's dismembered arm on a table and the rest of him hiding beneath it. Regina gets Whale to the Storybrooke Hospital. Prince Charming walks into the hospital demanding to know what happened. Regina says she doesn't know, she found him in his lab with his arm missing. Later in the episode, Dr. Whale walks to Rumplestiltskin's shop with a cooler on his right shoulder. When Rumplestiltskin asks what he wants, Dr. Whale opens the cooler which has his arm inside, and says he wants his arm reattached. Mr. Gold tells Dr. Whale to say "I need magic", referencing Victor (Whale) saying that science was more powerful while they were in the Fairy-Tale World. When Whale reluctantly does, his arm is magically back on his body. ​("The Doctor")