I don't think he was arguing against paying taxes, I think he was arguing that there are _some_ transactions which it is reasonable to expect both a level of privacy, as well as obscurity to the government for purposes of dissent or lack of relevant jurisdiction (private, ad-hoc transactions are still a thing).

e.g. purchasing large amount of print materials / equipment or other distribution tools that are then flagged / targeted by a less than agreeable local political group to repress participation

While federal laws "sound" nice, enforcement and targeting of most laws are still done by local, less arguably democratic practices