In the Dodge Junction town square, a tall, dark pegasus in a postal uniform was checking over his straps and buckles one last time in front of some admiring onlookers. His dark fur shone in the red light. A honey-colored mare came up to his side.

“Been a long time since I’ve seen a pony in uniform here,” she said. “My name’s Sugar Roll. What’s yours?”

“Tale Spin,” he said. “Two words.”

“I saw you dancing with some of the mares at the hoe-down last night,” she said.

“The mares of Dodge Junction have been very welcoming to this humble mailpony,” he said.

“You’re so brave,” she said. “Travelling through the waste, with all those raiders lying in wait for you.”

“Just doing my job, Ma’am,” he said. He reached up and straightened his cap.

“Well, Tale Spin,” she said. “Maybe next time you come, I’ll have a letter for you.”

Tale Spin lifted his head and gazed off stoically to the north. “I can’t say for sure as I’ll make it back, ma’am. Raiders and monsters at every turn, and all. But duty calls, and I answer. Now, my fellow carriers await me.” He snapped her a salute and flew off into the sunset.

“Damn fool can’t see a thing, flying into the sunset like that,” an old grey mare standing nearby said.

Sugar Roll sighed. “But it looks so fine.”

“Also, Appleloosa’s that-a-way.”

“Hey,” Sugar Roll said. “Why do we always call it the sunset, anyway?”

The grey mare blinked. “I don’t follow.”

Sugar Roll shaded her eyes with one hoof. “You ever think that maybe it’s a sun rise?”

.

.

Author's Notes:

The Mailmare took 7th place in EQD’s More Most Dangerous Game contest, 3rd in the Fallout: Equestria-inspired stories. I didn't read most of the stories that beat it, so I don't have an opinion on that. I'm hyper-aware of what I think the problems are with the story. But I think more readers are bugged by things I did deliberately.

There are only two kinds of stories about good and evil:

1. Stories in which virtue is rewarded and evil is punished
2. Stories in which virtue is not always rewarded and evil is not always punished, and a major theme of the story is angsting about this fact

There are only three kinds of stories with villains:

1. Stories in which the villain loses
2. Stories in which the villain is reformed
3. Tragic stories in which the villain wins

But Fallout: Equestria (F:E) is not any of those five kinds of stories. F:E is a story in which the hero and the reader gradually realize that the world didn't come with a guarantee saying virtue would be rewarded, and that when you're tossed into a world where ponies are being killed, the important thing is not to go around judging people and dispensing justice, but to stop the killing. Virtue is not rewarded and evil is not punished, and that's beside the point. The failure of the world to meet your childish expectations is no excuse for despair, nor a reason to angst instead of rejoice when you've stopped the killing.

Which brings us to Tale Spin. Tale Spin is the bad guy. Or is he?

Well, he is pretty bad. He wants to be bad; he's trying to play the part of a bad guy. But he's an actor first. He'd rather be the hero, but if he can't be the hero, then he wants to be the bad guy. What he really is, is a self-absorbed douchebag. Bad, but no worse than some people you encounter every day. I wanted to show that it doesn't take a black heart to do evil things. Just a warped sense of priorities, or stupidity, or apathy. The problem isn't in the pony as much as in the environment.

In the end, Tale Spin wins. He gets exactly what he wants: to play the hero and to be adored by pretty young mares. Derpy has used him and neutralized him, but not punished or reformed him.

I already compromised on that point by suggesting that he never actually raped or killed anypony, and by making him slightly comical toward the end. But I definitely wanted to end with Tale Spin no better than he was before, and for that lack of reform or punishment not to detract from the triumph felt at the ending. Derpy has gotten past her desire for revenge in order to do the important thing, which is to stop him and to use him to help other ponies.

(I'm not saying revenge or punishment are bad. Just that the real world, unlike the worlds we see in books and movies, doesn't make sure that you never have to choose between saving the world and punishing the villain.)

InquisitorM said that this story is very pony because the ponies don't save civilization by using the Magic Doodad, but through individual personal connections. I think that's right, but it has an unpopular twist to it: Moral progress isn't made by teaching ponies the magic of friendship, but by delivering the mail. Now, that mail wouldn't be as important if ponies didn't care for each other. But while love and friendship might be the most important things, they aren't great points of leverage for social change. For thousands of years, people have tried to improve society by teaching people to be nicer to each other. This is a good thing, but not as effective in doing good as ignoble economic development.

Historically, humanity's moral progress over the past few thousand years, though it has ebbed and flowed, has not been due to people getting nicer, but to technology. The Dark Ages were not ended by Christianity; they were ended by the horse collar, the loom, irrigation, three-field crop rotation, wind mills, water wheels, paper, trade routes, the invention of corporations, insurance agencies, banks, and all the things that made it more profitable for people to make stuff than to fight over the stuff they already had.

In the end of this story, Tale Spin is just a harmless douchebag. He was never "reformed"; he was put into a different environment in which it doesn't pay to behave in his old ways. Millions of douchebags today might rape and kill to get what they wanted if they found themselves in a wasteland devoid of law and order. We don't kill them all, satisfying though that might feel; we build a society in which they can get what they want more easily by doing other things.