"All magic comes with a price." Rumplestiltskin's iconic quote from Once Upon A Time represented the transactional nature of all magic and the events that defined Rumplestiltskin's life. He was the most cunning and powerful villain of the show, whose elaborate schemes were always ten steps ahead of everyone else. Just like his memorable quote about magic, though, many of Rumplestiltskin's gains also came with losses and vice versa.
He was often responsible for other characters' suffering, but he also suffered a great deal of tragedy and loss in his own life. His path to redemption was not a straight line as he often regressed and slipped back into his old ways before he finally changed for the better and earned lasting redemption.
10 Felt Bad: Unable To Go Through The Portal With His Son
Baelfire wanted to be with his father, but not while his father continued to be corrupted by his Dark One magic. Rumplestiltskin and Baelfire agreed to go to a land without magic so they could be together and Rumplestiltskin would no longer be corrupted by his magic.
When the portal opened up, Rumplestiltskin's cowardice got the best of him and he was unable to go through the portal. He let go of Baelfire's hand and his son fell through the portal, leaving them in different worlds. He immediately regretted what he'd done and wanted to be reunited with his son. This mistake haunted him for the rest of his life and he spent centuries trying to correct it so they could be together again.
9 Hated Him: The Deal With Cinderella
Desperate to escape her wretched life and attend the royal ball, Cinderella made a deal with Rumplestiltskin and signed a contract so he could transform her into a beautiful princess. The problem was she didn't know what she'd agreed to in return, which turned out to be that she would have to give her firstborn child to Rumplestiltskin.
It was cruel of him to take advantage of a desperate, mistreated young woman. He held this deal over her after she got married and became pregnant and tried to take her child from her in Storybrooke.
8 Felt Bad: Abandoned By His Father
In order to regain his youth and attain the ability to fly, Rumplestiltskin's father Malcolm was willing to abandon his son. Malcolm stayed in Neverland and became Peter Pan while the Shadow took Rumplestiltskin back to the Enchanted Forest.
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Rumplestiltskin grew up without parents and the knowledge that his father valued his youth and power over his own son. All Rumplestiltskin wanted was to be with his father, yet Malcolm abandoned him and had the audacity to tell Rumplestiltskin that he was holding him back.
7 Hated Him: Rejecting & Replacing Zelena
When she was a baby, Cora abandoned Zelena in the woods. Zelena's adoptive father constantly belittled her and shamed her for her magic. Zelena thought she finally found a positive mentor in Rumplestiltskin. He taught her how to control and channel her magic, all so he could use her to cast the Dark Curse.
The caster of the Dark Curse needed to kill the person they love most. When Rumplestiltskin realized he was the person Zelena loved the most, he knew there was no point in her casting the Dark Curse for him. He cast Zelena aside and soon after relied on her sister Regina to cast the Dark Curse instead. Rumplestiltskin became yet another person who made Zelena feel worthless.
6 Felt Bad: Controlled & Held Captive By Zelena
With the Dark One dagger in her possession, Zelena was able to control Rumplestiltskin and keep him captive. She kept him imprisoned in a cell and tried to provoke him into resisting her, though they both knew he was powerless to do anything while she possessed the dagger.
She repeatedly humiliated him and used him to complete tasks that could make her time travel spell possible. This would've been brutal under any circumstances, but was even worse when considering that Rumplestiltskin was grieving over the death of his son. Rumplestiltskin had also been resurrected against his will, only to be Zelena's puppet.
5 Hated Him: Using Hook's Death To Become The Dark One Again
Hook sacrificed himself so he and Emma could destroy the Darkness and save everyone. Rumplestiltskin took advantage of Hook's death by turning Excalibur into a conduit. This meant that instead of destroying the Darkness, Excalibur was actually transferring it to Rumplestiltskin. He was now the Dark One again and had the combined power of every Dark One who ever lived.
This selfish betrayal meant that Hook died in vain. Rumplestiltskin had fooled everyone once again and found a loophole for his own gain, only this time the consequences were deadly.
4 Felt Bad: Baelfire's Death
Rumplestiltskin spent centuries trying to reach the Land Without Magic so he could reunite with his son Baelfire. They eventually reunited, but it wasn't long until Baelfire lost his life for good. Zelena manipulated Baelfire into resurrecting Rumplestiltskin.
Rumplestiltskin relinquished the Dark One dagger and absorbed his son's body to prevent him from dying, yet this only worked for so long. Baelfire's fate was already sold and in the end, he did die. Rumplestiltskin lost the son he'd worked so hard to reunite with and who he'd missed dearly.
3 Hated Him: Lying To Belle About The Dagger
Unable to relinquish his power, Rumplestiltskin led Belle to believe that he was a changed man. He gave her the Dark One dagger to show that he didn't care about his power and only cared about her.
The dagger he gave her was a fake, though. He continued to deceive her and do deplorable things behind her back with the real dagger until she finally discovered the truth and banished him from Storybrooke. He was a terrible husband for constantly lying to his sweet and supportive wife who saw the good in him when no one else did.
2 Felt Bad: Losing Belle
Rumplestiltskin finally changed for the better and became the good man Belle always saw in him. They built a beautiful, blissful life together, shown to the audience in a montage inspired by Carl and Ellie Fredricksen's love story in Up.
Belle grew old and eventually passed away. Rumplestiltskin lost the love of his life and had to live on due to the immortality of being the Dark One. He was ultimately reunited with Belle in the afterlife, but it was still devastating to see him lose Belle and have to live without her for a while.
1 Hated Him: Throwing Milah Into The River Of Lost Souls
Milah was unable to move on from the Underworld because of the guilt she felt for abandoning Baelfire. Still bitter over her leaving him and Baelfire, Rumplestiltskin told her, "Congratulations, Dearie. I've finally become the man you always wanted me to be. The one who takes what he needs."
As she cried out for help, he used his magic to throw Milah into the River of Lost Souls. This was a fate worse than death as it meant her soul would be forever trapped and tormented, unable to ever move on. Rumplestiltskin even manipulated the scene of the crime so Emma and Hook believed that Hades was the one responsible for Milah's fate, a lie and horrific action that Rumplestiltskin never reconciled with or revealed.
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