In fairness, just because most of the regulars want to swing at the best, doesn't mean there isn't a problem.
For me... well, I don't enter the contests. I keep meaning to but 1500 words is too much for me unless I really love the idea. But when I enter, its to enjoy writing and learn what I can afterwards. I love winning, but that's secondary, and only means something if I'm beating the best.
Well, I thought it might be an issue, but given what most everyone is saying, it doesn't seem to be.

To give some background, I started thinking about this a few months back, when a couple of new entrants to the contest expressed some trepidation about entering. I want to say it was when we were jokingly throwing around the "God Emperor of the Writing Contest" title, but I think it was also a case where some new posters specifically asked about how often new people win, because we'd done some math about multiple winners.
Personally, I don't think there's any bias toward regulars (I always vote for what I feel are the best stories, despite how difficult you awesome authors make it to decide, and I feel like pretty much all of you do the same) but I was more worried about the *appearance* of an advantage. As everyone knows, sometimes you don't actually need to have a problem ... you just need to suggest that there might be a problem, and people will react accordingly. However, judging from the points everyone has made on this thread, it seems like putting a "cooldown" on winning would do more harm than good.
I think the best solution is to just take every opportunity we can to encourage newbies to enter again (I usually try to drop the authors of the stories I vote for a PM, to let them know how much I enjoyed what they wrote) and just nip those worries in the bud whenever they come up.
Also, as I told Xiagan, I think our monthly contests are about my favorite thing ever. I have written *so* many stories I would never have written as a result of our themes (really? A pirate story?) and as flattering as it is the times I have won (thank you!) just the process itself feels like its own reward.