Would this award have content?
Sorry, I'm not sure what you mean.
I'm thinking it would go something like this: users would be encouraged to track examples of contrarian contributions. At the end of the month, there would be a nomination process (with pointers to examples of contrary statements) and then voting on who was the best contrarian. (Whoever maximizes quality of statements degree of disagreement with other users at the time they wrote the statements. Number of contrary statements made could also be a multiplier, although that might be a bad idea if we want to avoid flooding LW...
I'm worried that LW doesn't have enough good contrarians and skeptics, people who disagree with us or like to find fault in every idea they see, but do so in a way that is often right and can change our minds when they are. I fear that when contrarians/skeptics join us but aren't "good enough", we tend to drive them away instead of improving them.
For example, I know a couple of people who occasionally had interesting ideas that were contrary to the local LW consensus, but were (or appeared to be) too confident in their ideas, both good and bad. Both people ended up being repeatedly downvoted and left our community a few months after they arrived. This must have happened more often than I have noticed (partly evidenced by the large number of comments/posts now marked as written by [deleted], sometimes with whole threads written entirely by deleted accounts). I feel that this is a waste that we should try to prevent (or at least think about how we might). So here are some ideas: