Despite the existence of the E.Hughes soda.berkeley.edu FTP site he lamented a lack of consolodated information about the cypherpunk movement and goals, i.e. in a FAQ form. Something as simple as a list of the cypherpunk remailers was not even available. He built up a list of the remailers and this formed the basis of one of his early FAQs, Identity, Privacy and Anonymity on the Internet, and a later one, Anonymity on the Internet. The latter branched out of his interest in promoting the Helsingius server (anon.penet.fi) that had just been established. (This server has almost been too successful for its own good, after the initial lightning hostility it become popularized around the entire Internet and while still alive is burdened by massive traffic.)
It became clear that Detweiler's flashy posting style offended the California cypherpunk founders. His frequent and elaborate articles tended to eclipse other members, and Detweiler had a small tolerance for what he perceived as ego-assuagement, pretension, or hypocrisy. Frequently he was in the middle of massive flamewars on the list with a now infamous "no holds barred" inflammatory style. But he also posted many neutral and creative posts on the core Cypherpunk topics of cryptography, remailers, politics, governments, digital cash, PGP, the NSA, etc., as well as minute analyses of current events involving cyberspatial developments. He was enraged at the introduction of the Clipper chip and immediately posted extremely hostile letters attacking D.Denning, and lobbied long and publicly against the key escrow scheme.
Detweiler seemed at first to come to the conclusion that the list politics was dominated by the "CA Clique" factor: the California posters and founders of the list, at the same time inviting people from around the world to join the "public" list, simultaneously ridiculed the outsiders when their opinions conflicted with the leaders'. Detweiler felt that this was extremely dishonest and troublesome, and highly destructive to group spirit, morale, and unity.
Detweiler called the practice "pseudospoofing" and said that it was "close to the number one crime by cypherpunk standards" because it involved deception in identity, and the integrity of identity was essential to the privacy the cypherpunks advocated through encryption. (Roughly speaking, the term "spoof" in the cryptographic vocabulary is the situation where an "attacker" deceives a "sender" about his identity and thereby gains access to secret messages). A key, subtle component of his arguments claimed that the cypherpunks are actually interested in a kind of clandestine pseudonymity, a sort of "pseudoanonymity" in which the receiver of a message is systematically tricked into believing in the existence and credibility of anonymous entities. Detweiler explored the issue in depth and from many angles in many posts over many months, provoking a cyberspatial flamewar of legendary status.
At first Detweiler beseeched the cypherpunk "leaders", who he regarded T.C.May and E.Hughes, and sometimes J.Gilmore, to "come clean" about what they were really advocating. He started in private mail but advanced and escalated his campaign to public forums, even newsgroups such as talk.politics.crypto. They either flatly refused or were evasive, or actually answered the questions by saying they didn't think there was anything immoral or unethical about "pseudospoofing" as Detweiler implied. With what he called their "stonewalling" Detweiler eventually became increasingly hostile and enraged, saying they had "betrayed" him.
Detweiler seemed to be amused at playing a game of hinting of his real identity in pseudonymous posts and the great commotions that their appearances caused. He appeared to delight in trampling on whatever cypherpunks considered sacred, including fanaticism for anonymity, and watching as an increasing majority of cypherpunks realized his secret identity. He also claimed at times that he was deliberately demonstrating the havoc that could be wrought through the use of what he called "pseudoanonymity" (when the reader of a message is not aware of the pseudonymous identity of the sender). He pointed to how much chaos he could sow with a single identity that everyone *knew* was anonymous, and that the dangers of fake identities not recognized as such were far greater.
This period involved a great number of cypherpunks mailing Detweiler or posting to the list to ask him to stop his "jihad". But Detweiler sensed that "the leaders" were stonewalling. As evidence, he alluded to all kinds of supposedly incriminating elements that he never really described. He became increasingly melodramatic and at times, seemed to post messages bordering on insanity. He invented new terms like "tentacles" or "Medusa" to describe the "rampant pseudospoofing" on the cypherpunks list that he claimed was "brainwashing" innocent, unsuspecting outsiders. He claimed that "double agents" were tormenting him by filling his mailbox with attempts to glean his secret knowledge. His paranoia surpassed even the heightened degree of the cypherpunks who had themselves elevated it almost to a religion.
However, deep in all the vitriolic froth he was routinely posting to the cypherpunks list to deliberately provoke massive flamewars (saying this was like giving anarchists a taste of their own medicine), Detweiler did eventually allude to two important facts he had uncovered in private mail to cypherpunks. Detweiler claimed that T.C.May once wrote him in a message in which he admitted to "experimenting" with pseudospoofing but stopping later. This seemed to be inconsistent with later claims of May's that he had "never" used the practice. Another private message he received supposedly came from Doug Barnes, who said that the practice of pseudospoofing was liberating, and that E.Hughes had introduced him to the practice.
Other anomalies were present. E.Hughes wrote to Risks that he had never posted under an identity other than his own. But the message was worded in such a way as to seem to imply that he didn't even use anonymous remailers, ever (a farfetched position considering he had himself helped to invent them). The "leaders" did conspicuously refrain from posting any indication of whether they had used the technique, or wrote long or terse defenses of their "privacy" or the practice itself. Hughes wrote, "that which cannot be enforced should not be prohibited". May and Gilmore wrote similar defenses.
Detweiler began to see even more sinister conspiracies in the cypherpunks. He said that they were really involved in a propaganda campaign across the Internet to promote anarchy, black marketeering, tax evasion, pornography distribution, etc. in different newsgroups and mailing lists. He said that they may be involved in bribing reporters or at least had questionably "cozy" ties to them. As evidence of possible deceit, he said he had been unable to find the photographer Larry Dyer of the first Wired Cypherpunks article, and he suggested that the name was fictional. He said that the cypherpunks were manipulating the media to glean articles that championed them as "digital freedom fighters" and mask their more subversive agendas. Detweiler claimed that the heart of their cynicism about governments disguised the cypherpunks' real stance: anti-democracy anarchism.
Detweiler was particularly inflamed by and hostile to T.C.May, a retired millionaire chip engineer who worked for Intel. May invented a organization he called "BlackNet" that was interested in selling industrial or political espionage secrets. The scheme was for the system to work via anonymous remailers and encrypted traffic, and the early public announcements introducing its existence were posted anonymously. Detweiler claimed that May was behind the organization. After many months, May did eventually admit that he had invented BlackNet, but only as an "experiment". Detweiler claimed that to the contrary May was seriously interested in the aims of Blacknet.
Detweiler also began to experiment with cypherpunk remailers more assiduously. He began to post his messages to diverse newsgroups in what appeared to be more desperate attempts to exert pressure on the cypherpunks to "come clean" about their true agendas. These variously depicted May as a Nazi who was using identity-subversion techniques of the Germans used in WWII, comparing pseudospoofing to a real German espionage effort called "Operation North Pole". He invented a satirical game called "SQUISH" attempting to get others to find, pursue, and hunt down people posting "pseudoanonymously", sending it to about a hundred mailing lists through the cypherpunk anonymous remailers.
It does appear that Detweiler was behind a prolific alias, firstname.lastname@example.org, who posted many messages, posing as different people, to talk.politics.crypto and news.admin.policy before apparently being censored by Netcom administrator Bruce Woodcock. email@example.com delighted in tasteless irony such as posting vicious satire under a signature such as "Beavis N. Butthead", and then turning around to complain about its vituperative tone as "Linda Lollipop".
The person posted private mail received in newsgroups, and was one of the most deliberately offensive and insulting entities to grace the Internet in recent times. firstname.lastname@example.org was particularly hostile to T.C.May's "cryptoanarchist" agenda, but out of boredom seemed to seep into news.admin.policy to criticize news administrators for their "capricious" and "oppressive" policy of censoring users without a systematic review or universal guidelines, something he was certainly qualified to speak about from experience.
For his legendary crackpotism he has been awarded a place in FAQs dealing with the subject and continues to be a lodged residue in the collective Cypherpunk consciousness. Detweiler if nothing else is persistent and behaves with the fanaticism characteristic of ideologues who believe their ideas are intrinsically important and true and if not recognized as such in their own lifetime will nevertheless be seen as world-shattering from the perspective of historical retrospective.