Sully's "career" as a thief didn't last very... well technically it did last a long time. Most of his life, actually. He just doesn't like to dwell on it.

He mostly did it to put food on the table for himself and his siblings, to make the ends meet that his deadbeat father refused to take care of himself. And, yes, he sometimes stole purely to make his own life a little more comfortable. Because why shouldn't he, you know? If you're already in deep with something, what's a little more digging?

You can probably extrapolate from there what his mindset was, his attitude towards life and society. You'd very likely be wrong, and the way that you're wrong is why he prefers to put that part of his life in the rear view mirror.

You see, the problem isn't with the self-entitled privileged assholes. The people born with proverbial silver spoons in their mouths. They're around, and they don't exactly make life better for the "down and out" but on a practical level they're pretty easy to have nothing to do with. There really aren't that many of them.

And it doesn't lie in the opposite direction either. The people who come up from the gutter, who bust their asses and pinch every penny and work 100 hour weeks and then turn around and blame you for not showing the same "initiative". They're not hard to deal with either, if only because it's easy to see they have a complex. You send them a "get well soon" card and leave them be.

No, the trouble comes from the hordes in the middle. The "normal ones" who've landed on islands of stability through a perfectly quotidian mixture of hard work, good luck, and having the right people stick their necks out for them. They know—they KNOW—that if things had gone slightly differently they'd be struggling, "down and out", maybe breaking the law every now and then to make ends meet.

But they can't help themselves. When they meet a Marcus O'Sullivan they immediately execute one of three hardcoded programs.

Program One: Pity. It's so terrible what happened to you. It's a shame that kids have to grow up under those conditions. Society should really do more to help underprivileged youth. If there's anything I can ever do for you, please don't feel ashamed to reach out.

Program Two: Pity. It's so terrible what happened to you, but look at what you made of yourself in spite of your circumstances! It's a shame your mother's not around. I'm sure she'd be very proud of the fine young man you've become.

Program Three: Pity. Although this one's a doozy because they try to hide it. They mask what they think of you, self-consciously try to treat you like "one of the guys" but the effort they're investing in their lie is written all over their bad poker faces and you just want to slap it off them.

You see the issue? With the normal ones? Whether they go left, right, or down the middle the train always winds up at the same station. Their helping hands, their gestures of trust, the subtle sneers and guarded expressions that slip past their defenses. You can't send them a "get well soon" card because they're not sick. They're perfectly normal.

So he doesn't talk about it. He's not Marcus O'Sullivan. He's Sully and that's that.

When Sully started coming to Jeremy's DnD games he had to pick a character class. Some of them suggested he pick a Rogue. A sneaky thief. "It's so like you, don't you think?"

Well, he didn't want to be a Rogue. What's the point of fantasy if not to aim a little higher?

Aim it right over their heads. Hit the target none of them can see.

DnD YCH by  TheDammitch