Without a doubt the guy is a looney. Damn stretch to consider this free speech that should be protected. Obsessive behaviour, multiple psedonyms, telling porkies. How is all this not "uttering threats" ?!? The following is a quote from this Canadian website about the Criminal Code of Canada (http://www.defencelaw.com/utter-threats.html):
"What the Crown must prove
To secure a conviction at trial, the Crown must prove that the person making the threat did so knowingly. That is, the prosecution must show that he was aware of the words used and the meaning they would convey. It also must show that he intended the threat to be taken seriously, that is, to intimidate or strike fear into the recipient. It is not necessary that the person making the threat intend to carry it out or be capable of doing so. The motive for making the threat is equally irrelevant.
In assessing whether the words constitute a threat, they must be considered objectively. The court must ask: In the context and circumstances in which the words were spoken or written, the manner in which they were used, and the person to whom they were directed would they convey a threat to a reasonable person?
A history of violence between the parties may support a finding that the words were intended as a threat. Whether or not the person making the threat has an apparent ability to carry it out when the words are spoken, his use of gestures or acts, whether the recipient of the words takes them seriously, and disparity in size between the speaker and the recipient of the threat may all be relevant to an assessment of the speaker's intent."
The Right to Free Speech shouldn't be a club that turns on the nuance of phrasing. IANAL, but in Canada I'd say he'd be convicted.