So two people basically rotate winning this contest? Think I'll be passing on this event in the future.
In the past 12 months, we've had 8 different people win. This contest isn't biased towards any particular person (Hell, I first won after I'd only been here a month or two), it's biased towards who can write the most entertaining story. I'm good at that, thanks to my comic talents, which is why I win a lot. But I'm far from perfect. I've lost a lot of contests, even with comedic stories. But if you write a good enough story, people here will sit up and take note.
But the one way you're absolutely certain to lose is if you give up and not bother entering just because you're frustrated with not winning. First time I ever entered this contest, I only got 2 votes for my story. If I'd thrown in the towel then, decided it wasn't worth it, where do you think I'd be? Certainly not with the 5 wins I have now.
Besides which, you're missing that winning isn't the only point of the Writing Contest. Certainly, the wins are nice and all, but the thing I got the most out of the Writing Contest was experience. Experience from coming up with interesting ways to play with the chosen topic, from writing up a story that feels well written and well paced and naturally fits into the short story format, and from tirelessly clipping away to actually try and get the blasted thing under 1500 words. And enjoyment as well. Because I, like most people on here, enjoy writing. Otherwise we wouldn't be doing it. Certainly, it's often disappointing if you lose, but that doesn't undo the progress you've made and the good times you've had.