I think that the part that I have issue with is that people have been having online discussions for far longer than moot has been around (hell, probably even alive). Unless you are aware of 4chan, you'd probably never even heard of him outside of a few news articles. 4chan and moot are well known within their own realms, but in reality, it is a small fraction of the "online discussion" world. So, when you're looking at applying trademark-level protection, it's not appropriate to look at the smaller realm, but rather the environment as a whole.

This all seems like a big-fish, small-pond vs. small-fish, medium-pond argument to me.

Moot maybe incredibly influential in his corner of the 'net, but the larger world probably doesn't know him. Moreover, the brand of his product isn't "moot", it's 4chan. To top it off, "moot" isn't a rare word, it's a commonly used word in English. All of this combines to make it very difficult for him to try to make any direct claims against Moot.it.