💀 Player Information
Name: Ros
Age: 31
Contact: rosloops
Characters In-game: Chase Collins

💀 Character Information
Name: Jefferson
Canon: Once Upon a Time
Canon Point: Sometime after the flashback events in 2x05, "The Doctor." Let's say he had a bad run-in with a tin woodsman and an enchanted axe (that he was trying to steal for an employer).
Age: Early/Mid-20s
Description: Jefferson stands at somewhat above average height (5'11"), with a lean and unimposing build. The kind of guy who looks like he'd rather get out of a conflict through persuasion and sneakiness than fists and force. With blue eyes and very expressive features, he tends to pull a lot of exaggerated faces, as if he wears his feelings openly-- even if he's probably putting on an act. Jefferson prefers to be clean-shaven, and his short, brown hair is rather unkempt, in a perpetual state of bed-head, POSSIBLY FROM WEARING HIS HAT TOO MUCH. He likes to wear pretty elaborate outfits in way too many layers: waistcoats, long jackets, scarves/ascots/cravats, hats, knee-high boots, in addition to, you know, shirts and pants. Each article of clothing tends to be patterned and they're of various different fabrics and leather trims, but coordinated in some capacity, so it's clear that he enjoys fashion and dressing himself up. He's shown to favor blacks and reds at this canon point, and he also wears a couple of tacky rings because he's A Very Cool Guy.

Lord knows how he'll handle the heat in Hell, given the way he likes to dress.

Physical changes: Jefferson is now the lucky owner of a set of sharp, black claws, along with black discoloration of his skin extending down past the first or second joints of each finger. They're going to take some getting used to and really mess with his ability to use any skills that require a delicate touch.
Powers: Jefferson's a normal human, but he's got a very special and very magical hat, which will be accompanying him to Hell. In canon, the hat acts as a portal, allowing him to travel between different magical realms, and it has a pretty inconvenient rule: the number of people who enter the hat must match the number of people leaving the hat. Too bad his hat won't work in Hell, so it's just a normal, totally impractical hat now.
History: Jefferson's History! Pretty much only "The Doctor" is relevant at this canon point, so have a detailed synopsis of that episode.
Hell Status: Hell Newbie
What Brings Them To Hell: At this point in his life, Jefferson gets by as a thief and a con artist. He's not a villainous guy, really, so much as he's a shady opportunist who doesn't really care much about others yet, which has led him to do the kinds of things that result in a person gaining a lot of enemies over the years. His generally grey morality would probably land him with a Limbo stamp, if not for the fact that his various crimes aren't exactly victimless. Jefferson knowingly played a significant role in manipulating Regina into becoming the Evil Queen (through deliberately getting her hopes up so that she would buy into his con with Victor Frankenstein and have all her hopes and optimism and goodness cruuuushed), which in turn led to the subjugation and deaths of who knows how many people during her reign of terror. He may not have known how cruel a ruler Regina was going to become, but he certainly was aware of the fact that Rumplestiltskin was out to make her into a 'monster,' and that Jefferson had to crush her capacity for love to do it.

The Pitch: Jefferson's the sort of guy who adapts so wholly to his circumstances that he essentially becomes a new person whenever there's a turning point in his life. While growth and change are normal parts of the human experience, Jefferson takes reinvention several steps further, doing it so completely that it's like he's trying to give David Bowie a run for his money. He's a sketchy but charismatic conman, wearing fashionable, showy outfits as he peddles lies. He's an impoverished, struggling single dad, devoted to his daughter, but weighted down by his inability to really provide. He's the Mad Hatter, utterly fixated on a single, impossible task to the point of mental deterioration. He's the eccentric recluse, charming one minute, and giving off major serial killer vibes the next.

When he changes his persona, everything shifts: his clothes, his inflections, his mannerisms. His capacity for reinvention gives him huge potential for growth and change, because he dives headfirst into whoever his circumstances dictate he become. Others from his world tend to have common themes or characteristics that follow them throughout their lives: power, cowardice, villainy, heroism, selflessness... Jefferson's consistent characteristic, meanwhile, is his malleability.

At this point in his life, Jefferson's at his most hellbound. Eventually, he would mature and devote himself to fatherhood (and later, he would lose his mind), but here, he hasn't yet found anything or anyone to ground him, to inspire him to be a little selfless. He lives for himself, and he enjoys reaping profits from stealing and conning. Everything about his demeanor is so affected, like he's Jefferson the Actor playing Jefferson the Character. He emphasizes words to exaggerated degrees, makes flourishing gestures with his hands, and pulls weird reaction faces in response to those around him.

So what you get is this semi-affable, occasionally off-putting weirdo. He doesn't even seem to be afraid of the Dark One. Where others cower before Rumplestiltskin, or treat him with any combination of respect, contempt, fear, and awe, Jefferson has a fairly friendly relationship with him. They're not buddies or equals, but that doesn't stop Jefferson from carrying himself casually and chatting with Rumple in the same manner in which he chats with everyone else. Whether you're a queen, an all-powerful imp, or a mad scientist, he'll pretty much treat you the same.

And as a portal hopping thief who's seen and experienced so many strange, magical worlds-- Wonderland, Oz, Universal Horrorville-- he has an understanding that each place operates by its own rules, and those rules must be adhered to. Because he hasn't been slammed with one tragedy after another yet (seriously, his life gets awful), it's easy for him to go with the flow and accept new places or situations, operating within each world's unique brand of weirdness. Maybe that's why he, too, comes across as a bit weird.

He may not be the Mad Hatter yet, but the seeds are there. And Hell is just another stop in his travels.

Setting Fit: So, Jefferson's going to be happy to leave all the ambitious "rise to the top and take over Hell/Brimstone/the criminal underworld" stuff to all those demons with a tendency towards megalomania. He'd much rather be a sort of shady free agent who can get you what you need (or want) to further your own plans. Yes, you, Demon with More Dracos Than You Know What to Do With. His hat may not be able to transport him to other realms anymore, but Jefferson still has a lifetime of thievery and con artistry to fall back on. In order to get his hands on things that can't be acquired in Hell, sure, he'll get himself a Reaper gig and a pair of Reaper gloves and go to town. But he can offer more than just smuggling. He'll sell your snake oil, deal in information, and get his hands on blackmail material. He can get those hard-to-find objects that may be in Little Hades or in other cities-- or maybe he knows a guy who knows a guy who can get it for you.

That's all the plan, anyway. It'll take time to learn the lay of the land and make the right connections. So, until then, he'll just have to do odd jobs (of the eclectic variety). Worse comes to worst, if all the niches for shady dudes have been filled by other enterprising demons, maybe he'll put his tailoring and millinery skills to use and get involved in the Little Hades fashion scene. Such as it is.

Samples: Several meme threads (one takes place in Little Hades)
Season 1 PSL Thread (different canon point, but shows more serious/introspective stuff)