This anthology from ebooksonthe.net contains a number of prize winning short stories from a group of talented writers.  J. Richard Jacobs won first prize for his convoluted, irreverent and strangely mainstreamish story, WINNING IS FOR THE LOSER.  Imagine making a wager that if you win, you lose.  What would cause you to make such a bet?  You can't get much more weird than that.  Now, can you?

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Here's an excerpt from WINNING IS FOR THE LOSER:

                                          9 August 1967

“Okay—how much are you willing to put up, dumb ass?”

“Five bills, plus a fifth of the best Irish to be found, my man,” Reilly replied, a confident smile spreading across his freckle spattered face. “Think you can handle that, dude?”

“I’ll tell you what, Chucky baby; make it an even thousand and you’re on,” Abe Spitzer countered, hoping that upping the ante would make the kid back down from this absurd nonsense.

This is not the kind of wager people out here make, he thought. It is—sick, that’s what it is.

Charley trapped him into this twisted, obscene conversation in the first place by putting him on the spot and, if it hadn’t been for Abe’s inability to back down from any challenge, no matter how crazy it was, he would have broken the thing off before it ever got that far—that serious...that crazy.

“I don’t know, man. Pretty stiff, don’t you think?” Charley said.

Maybe it’s going to work, Abe thought. Maybe the little jerk is getting ready to back away and call quits to this whole psycho-ward thing.

“Hey, Chucky, you’re the one who started this psychotic crap, remember? It wouldn’t hurt my feelings a little bit if you decided to get sane and forget this...this BS, you know?”

Abe bit down hard on his lower lip and watched for any positive sign that the youngster was going to come to his senses. It was the consumption of too much beer in this humid heat that had unscrewed the kid’s head and maybe, now that some time had gone by and it was beginning to cool off, well, as much as it ever cooled off out there in the summer, he was sobering up.

What Abe saw in that scrubbed raw, no-need-to-shave face angered him. Charley looked resolute—determined to go on with it. The damned fool was actually going to make the transition to complete craziness.

“All right, sucker, it’s a deal. A thousand bucks and a bottle of the best Irish whiskey money can buy—due and payable at the winner’s circle,” Charley said, grinning like he’d already won the race that wouldn’t start until the following month.