Jefferson wasn't a man who you might say had many scruples when it came to making money. He'd set himself up working for the Dark One a couple of years ago and very rarely questioned what the man wanted him to do. After all the money he got allowed him to provide for his daughter Grace. His pride and joy.
His relationship with Rumplestiltskin was an odd one certainly. He could still remember how he'd struck the bargain with the imp.
Penniless and on the verge of starving with baby Grace to feed he'd approached the man to make a deal.
Flashback*
Jefferson surveyed the strange man in front of him. Truth be told he'd seen scarier and stranger LOOKING than Rumplestiltskin but few had exuded the aura of power that this man did.
"What is it you want dearie?"
"I need gold, a regular supply of it. My daughter and I we're on the verge of starving at this point and I can't support her."
"Alright. Give her to me and I'll give you gold in return," Rumplestiltskin had said to Jefferson's horror and indignation.
"Not for all the gold in the world!" exclaimed Jefferson. "I don't want it for myself I want it so I can provide for my daughter she's my life. The most important thing to me." To his surprise Rumplestiltskin didn't seem angry by his refusal. Instead, he looked almost pleased as if Jefferson had passed some sort of test.
"What can you offer then?" he said.
"I'm a portal jumper. Or I was. My hat can take me and anyone I take with me to a different realm," said Jefferson.
"Any realm?" asked Rumplestiltskin looking suddenly hopeful.
"Only ones with magic," said Jefferson and the hope seemed to fade from the man's eyes. He wondered what was in a world without magic that the man wanted.
"But I can fetch things for you from those other worlds. Though I do reserve the right to abort a quest if it turns too dangerous. I won't leave my daughter an orphan."
"Objects in return for gold and the ability to turn back if it doesn't look like you'll make it out," confirmed the Dark One.
"Can I get that in writing?" asked Jefferson who had learned through his travels and a few mistakes that it was always smart to have things written out. The Dark One raised a brow but waved a hand to create a contract for Jefferson to sign.
*End Flashback*
After that he was significantly better off with regards to money. The Dark One sent him on errands and in return he would get enough gold to support himself and Grace.
Along the way he also realized the Dark One wasn't THAT bad. Oh, the man was ruthless with a wicked sense of humor but if you were on his good side there wasn't really much to worry about. Still the change in their relationship didn't come until his second year working for the man.
flashback*
"RUMPLESTILTSKIN! RUMPLESTILTSKIN! RUMPLESTILTSKIN!" he called desperately. There was a puff of crimson smoke and Rumplestiltskin appeared inside Jefferson's house.
"You know dearie normally I expect you to be the one to come calling on me." Jefferson didn't have time for banter.
"I need your help now. It's Grace," he gestured to the two-year-old lying on her cot unconscious.
"She's been poisoned by one of my old enemies! I'll do anything ANYTHING if you save her I swear it!" Normally Jefferson was careful not to make such sweeping bargains but for his daughter he'd hold nothing back. He's sell his very soul if that's what it took.
To his surprise as Rumplestiltskin turned his attention to the child. He saw the man's face soften slightly and concern flit across it. His normally high pitched, voice dropped slightly to a more human tone.
"Do you know what it is?"
"The Long Farewell," he said. He'd caught the bastard that did it before he'd escaped and forced the answer from him. Rumplestiltskin nodded. He disappeared a few moments later was back with a bottle. Jefferson helped Grace sit up as the Dark One poured the antidote down her throat. Grace's breath evened out and a wave of Rumplestiltskin's hand sent her to sleep. Jefferson breathed a sigh of relief.
"Thank you. What do I owe you?" To his shocked the Dark One shook his head.
"This one's on me dearie."
"What? But all magic comes with a price," said Jefferson. Not that he was complaining but he always held up his bargains. He didn't want anything coming back to bite him because he failed to fulfill his word.
"It does. But this one is on me. No parent should have to pay for their child's life," said Rumplestiltskin with a shrug almost sounding nostalgic. Jefferson held out his hand.
"Well, I appreciate it."
"Don't go spreading it around Hatter," the imp said a hint of his old tone back. "Goodnight."
*End Flashback*
It was that night that Jefferson realized Rumplestiltskin really wasn't the monster of legend but a man. And one with a fairly decent side to him at that. At least it seemed when it came to children.
From that night forward something changed they weren't just business partners. They were friends. Or well, as close as you got to being friends with Rumplestiltskin. Mostly it meant he could get away with bantering and teasing the man, and not worry about being turned into something nasty.
Rumplestiltskin was also the only person who knew the full story of how Jefferson's first wife had died. A tale he entrusted to very few.
So, when he was asked to help break Queen Regina's heart all over again with the help of Doctor Frankenstein. He didn't have much of a problem.
Once he returned from dropping the eccentric doctor back in the world without color, he found Rumplestiltskin waiting.
"So gonna tell me why you need the Queen to be utterly heartless?" he asked.
"Heartless is her mother I just need her to give up any idea of finding happiness besides revenge."
"Against whom?" wondered Jefferson.
"Her step daughter of course. Dear little Snow White has quite the mouth on her."
"Note to self. Teach Grace how to keep a secret," snorted Jefferson.
"It is a useful skill," quipped Rumplestiltskin.
"That still doesn't answer why you want her hell bent on revenge has it got anything to do with why you want to get to The Land Without Magic?" probed Jefferson. The Dark One glared.
"Has anyone ever told you that you ask far too many questions for your own good Hatter?"
"Yes."
"MAYBE YOU SHOULD LISTEN." Jefferson smirked but let the matter drop instead changing course.
"That bringing back the dead thing, would it have actually worked?"
"Not in the way he wants I expect," said Rumplestiltskin. "Dead is dead. There's no way to bring someone back exactly as they were."
"I see," said Jefferson slightly subdued. He'd known the answer deep down but the idea of gaining back Priscilla his wife well...it was tempting. As if reading his mind, the imp said in a slightly gentler tone than usual.
"What you would get back would not be your wife, or Gracelyn's mother."
"I know. I just...Grace is enough. She'll always be my world. But sometimes, I miss having someone by my side. And there are days I think about what it would be like if Cilla were still alive to raise Grace with me." A father was one thing but his little girl ideally could benefit from a second parent.
Not that he'd ever remarry just to give her a mother. He'd been around enough to know how disastrously that could work out for all parties involved. Usually, it just ended with resentment.
"Have you ever considered remarrying?" asked his companion. Jefferson shrugged.
"I'm not really looking. I don't imagine one gets lucky enough to have two loves in their lifetime. At least not us mere mortals. Not to mention you've said yourself I have a certain type of...madness the occasional woman at an inn might find enticing but probably isn't true love material."
"Hmmm. True love can spring up in the most unlikely places. I wouldn't count yourself out," said Rumplestiltskin looking oddly thoughtful.
"By that token the same could be said about you." Rumpelstiltskin giggled and held up a blackened fingernail.
"Ahh I'm not a man dearie. The Dark One can't love or haven't you been listening to the fairies lately?"
"I never listen to those multi colored morons," scoffed Jefferson who had no particularly like of fairies mostly due to their obvious hypocrisy. There were plenty of people out in the realms that could use fairy help and the buzzing little brats did nothing.
"Quite wise," said Rumplestiltskin with a smirk. Jefferson knew that for some reason or another the man DESPISED fairies.
Secretly he also thought the old imp was being a bit tough on himself. Surely anyone deserved the opportunity for true love? Including the Dark One? Especially when said Dark One was less the personification of evil so many claimed and just a morally grey man with a morbid sense of humor.
If there was one conclusion Jefferson had come to through his travels it was that people were complex.
So if he was forming something that approximated a friendship with the Dark One? Well, who was to say that was such a bad thing?
OUAT
Jefferson was a man Rumplestiltskin respected. Though he wouldn't say it aloud. The Hatter would go to the ends of his earth for his child and Rumple admiredthat. It reminded him of his years with Bae.
He also happened to be very useful and tolerable company. Irritating but in an almost endearing way that grew on you through exposure.
Thus, he was pensive after their outing with Frankenstein. The man's musings of loneliness and not ever expecting to find love again reminded him a bit of his conversation with Pip.
Truth be told now that he considered it those two might just be a good match for each other. Both had their own brand of...madness one might say and Jefferson was certainly not one who would be bothered by Pip's more bloodthirsty tendencies.
Yes...that could be interesting. Of course he didn't NEED the match. He already knew the pinnacle of true love in the form of Snow White and Prince David would come later. But he was still a fan of true love. There was no reason he shouldn't have some fun playing match maker with his two favored partners.
Author's Note: And so! We get the backstory on the Hatter and his relationship with Rumple! I will always mourn the fact that we never got more Rumple and Hatter content in the show. Next time, our two leads finally meet! If you like the story or even just have thoughts PLEASE leave them below I'd love to hear them and it really helps with motivation! Until next time!