Fairytale 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.
The Dark Curse in Exchange for Riches and Comfort
In exchange for the secret to completing the Evil Queen's Dark Curse, Rumplestiltskin demanded riches and comfort in the real world of Storybrooke, and that the Evil Queen has to give him anything he asks for as long as he says "please." It is known that Rumplestiltskin's counterpart, Mr. Gold, remembers making this deal probably because it was initially his spell that he gave to the queen, and is shown he remembers after Regina demands his real name with which he answers "Rumplestiltskin".
Marionette Potion in Exchange for Jiminy Cricket's Parents
In the episode "That Still Small Voice", it is revealed that 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.
Cinderella's Night at the Ball in Exchange for her Firstborn
In "The Price of Gold", Rumplestiltskin destroys Cinderella's Fairy Godmother just afer 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.
Rumplestiltskin's Freedom in Exchange for Prince Thomas
When Cinderella confesses the terms of her deal with Rumplestiltskin to Prince Thomas, he concocted a plan to trap Rumplestiltskin. Thomas gets a red quill enchanted by the Blue Fairy that will freeze and neutralize the magic of anyone who uses it. Cinderella tells Rumplestiltskin that she wants to make a new deal with him. She tells Rumplestiltskin that she is pregnant with twins, and she will give both children to Rumplestiltskin in exchange for good crops in Thomas' kingdom, if Rumplestiltskin will sign a contract using the red quill. (The deal is a ruse; Cinderella is not pregnant with twins.) Rumplestiltskin warns Cinderella that she should not try to trick him because "all magic comes with a price," but he signs the contract nonetheless. The quill freezes Rumplestiltskin and he is imprisoned in the dwarves' mines. However, Prince Thomas mysteriously disappears. Rumplestiltskin tells Cinderella that the Prince wouldn't return to her until Rumplestiltskin's original deal was honored.
Prince Charming in Exchange for the Location of the Fairy Godmother
In the episode "The Shepherd", it is revealed that 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, 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 asked Rumplestiltskin for help, Rumplestiltskin brings him the son's twin brother in exchange for the location of the 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 Charming.
Potion of Forgetfulness in Exchange for a Lock of Snow White's Hair
In the episode 7:15 A.M. 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.
Protection from the Ogres in Exchange for Belle
In the episode "Skin Deep" Rumplestiltskin made a deal with Princess 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.
Snow White's Location in Exchange for Prince Charming's Cloak
In the episode "Heart of Darkness" 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. Charming takes off his cloak and Rumplestiltskin show him a map of where Snow is. 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's hair to form a true love potion.
Baelfire's Happiness in Exchange for his Powers
In the episode The Return, Baelfire wants his father to give up his powers. 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 afterwords and regrets this decision with all his heart. (Note: This is the one deal Rumplestiltskin has broken.)
The Looking Glass in Exchange for an Unspoken Action from the Evil Queen
In We Are Both, it is revealed that Rumplestiltskin first encountered Regina when she was desperately trying to escape form her mother's clutch. He gave Regina the Looking Glass which she later pushed Cora into. In exchange, he only replied that he know that someday she would do a favor for him. This "favor" is highly casting the Dark Curse (due to the fact that Rumple, at that time, didn't have neither Baelfire or Belle, as the heart of "the thing you love the most" was a key ingredient for the curse), sending him to our world in order to find his son.
Storybrooke Deals
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. 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.
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 publically 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.
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 sizeable 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.
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 a grand 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.
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.
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 previously.
Assisting in Revealing 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.
Helping Regina make Mary Margaret look guilty
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.
A Person-finding Potion 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 FTL. 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.
Cora's Old Spell Book in Exchange for Regina's Silence about Fairytale Land's Existence
When Gold found Regina in his shop, Mr. Gold asked her to leave by saying "Please", after discovered her motive is retreated her mother's old spell book. However, Regina refused and threatened to expose the existence of FTL. He reluctantly agree but as she was leaving the shop, he commented that he was wrong when he first thought that Regina doesn't like her mother. Regina later broke this deal when she told David that FTL still existed.