Benjamin Murray
THE BASICS:

Name: Benjamin Murray
Nickname: Ben, Benge, Benny Boy
Company Name, Business Name, High School Name:  He's self-employed... wait no... uhm... he works for Schuyler High School as a... history teacher.  Or maybe an actuary for an accounting firm.  He hasn't decided yet.
Are you related to Uncle Jerry? No
If not- how did you come across the invitation?  Well, that's the darnedest thing, isn't it?  It just showed up in my mailbox one day.  I knew about the contest, of course, who didn't know about it, but why me?  I can't say.

Note: The above, of course, is an absolute lie.  He got the 'ticket' from Sam Morten, a less than reputable loan shark (though Sam would claim to be a legitimate club owner).  As for where Sam got it?  Ben could guess, but he'd rather not think about it.

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PHYSICAL DESCRIPTION:

Gender: Male
Age: 30
Hair: Light brown and tangly
Eyes: Soft green
Distinguishing Marks:  He has just the slightest hint of buck teeth,
Description of General Appearance:  At 5'10" and 180 pounds, he's relatively fit, fit enough it would seem he probably works out.  Going for the absent-minded professor/over-worked accountant vibe (whichever he is), he tends to be a little messy, hair a bit askew, ties never quite straight, collars needing a bit of fixing.  Then again, if anyone with a sense of fashion were to think about it or better yet, check his labels, they'd realize he might pay more attention to his appearance than it seemed, that or he was just a terrible accountant and not very frugal with his money (or teacher at a really posh private school who married into money or something).

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UNDER THE HOOD:

Personality:  Ben's practically a cliché absent-minded professor.  He tends to scratch his head a lot like he's thinking (hence his messy hair), chews on his glasses, forgets where he put his pen, paper, glasses, keys.  But those are more mannerisms and quirks than personality.  He's friendly, inquisitive, smiles easily.  He comes across as either monumentally naive or deeply manipulative (no one can be that nice, right?).  He doesn't seem to have a care in the world, at least not when anyone's looking, though if you manage to catch him unaware you'll see that it's not remotely true.
Strengths: Ben's clever, good at reading people and knowledgeable on a wide range of subjects (though expert in very few).  He's an excellent gambler (though his current predicament might put that claim in doubt), and relatively fearless, or at least, not terribly afraid of failing (except in regards to his current situation).
Weaknesses:  He sometimes contradicts himself, is way too sure of himself and isn't always the best judge of when to take things seriously.
Fears:  Death, confinement (psychologically speaking), looking stupid (for real).

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SKILLS AND ABILITIES:

Education:
  Ben spent a few years in college but dropped out before getting a degree and is mostly street smart from there.
Special Training:  He knows how to pick simple locks, can do a few sleight of hand magic tricks (pick a card, any card) and is a decent pickpocket.
Talents/Skills:  Ben is pretty good at math, especially determining probability and odds.  He'd probably make a great actuary.  He's a good gambler and can read people pretty well (especially when they're lying).  He's a bit of a reader and knows a fair amount of history and current events, hence his 'job' as a history teacher.  Or actuary, he still hadn't decided yet.

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GETTING REAL:

Occupation/Position in Society:  High school history teacher or actuary.

Background/History:  Ben had a pretty easy life, a latch key kid to a family with money.  It might not have been Uncle Jerry money, but it was good old fashioned upper-middle-class money, enough that he never gave money much thought until he was in his twenties and didn't have so much.  He'd dropped out of school, mostly because he'd found it boring and wasn't really on any path, just taking classes trying to find something that clicked.  The only thing that ever really got him excited was taking chances.  And by that, he didn't mean bungee jumping or big wave surfing, extreme sports kind of chances, more the sort that involved making a bet and putting your future in the hands of fate.  Of course, he wasn't a sucker, he wasn't the sort to bet on a flip of a coin or a roulette wheel.  OK, that wasn't true, he'd bet on those, but he always played the odds.  He was no sucker, he bet on smart money, or if he didn't, he at least didn't bet enough to care if he lost.

That was why his current predicament was so troubling and made him suspect he'd been set up.  It had been a smart bet, practically a sure thing.  The 'double or nothing' that followed the same, the 'one last chance' even more so.  He was almost certain he was set up and set up for this.

The thing was, Sammy was a smart guy.  He was money smart and people smart.  He was also smart enough not to put himself on the line when he had others who could do his work for him.  That said, he didn't have a lot of smart guys on his side, most of them were bruisers or good at one thing and one thing only.  None of them would have been good with puzzles, heck, Roger had gotten himself locked in an apartment once, though he wasn't the brightest bulb of the already dim bunch.

Now, where Sammy got the ticket was a mystery, one that Ben hadn't bothered to try and figure out.  It was enough that he'd been offered a 'final final' chance and he was taking it.  It gave him two things, the chance to figure out how to get out of this mess, and the chance to take home the biggest payday of his life (assuming he could slip away with it without Sammy getting wind of where he went).

Come to think of it, he probably didn't even need to lie about how he'd gotten there, as far as he could tell, there wasn't anything in the rules about how you came about a ticket or why you were there.  He looked over the gold embossed ticket again, just to be sure there wasn't any fine print.

What is your character's opinion of Uncle Jerry's Game?  It all seemed a little crazy, but he'd been around enough insanely rich people to know they were all nuts.

What is your ultimate goal as you stand on the stairs of this mansion, waiting for Mr. Currier to say go?
  To win the game, get the money and disappear to some tropical island somewhere without an airport or phones or the internet or any way for anyone to ever find me again.  I'll take just the last part as a consolation prize.

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Writing Sample:

"And if I don't win?" he asked.  He knew the answer, he just wanted to hear it so they were all on the same page.

"Oh, you don't want to think about that," Sammy said with the sort of casual tone that could be mistaken as a shrug, a don't worry about it tone, just go and have fun, we'll see you when you get back.  It even had that tone that would make you believe they'd want to see your vacation photos and would ooh and aah sincerely when you did.  Sammy had a way with tones like that and had even been known to sound that way when taking a hammer to someone's fingers (or so Ben had been told).

"Right, right, of course not," Ben agreed, as though he didn't know what he was saying, worrying about something as unlikely as not winning a contest that was less about steering chance than it was about, well, he wasn't quite what it was about.  The puzzle of a house?  He didn't have a clue what that meant even after researching everything he could about Gerald Northhampton and The Reaches.  He'd even dug up what he could on the previous owners, Elmont Currier and as many of the Northhampton heirs as he could identify (though as far as he could tell, there were a lot of them and he'd only scratched the surface of the closest living ones).

No, Sammy was right, Ben didn't want to think about it, he didn't want to think about it at all.