alt Hacker NewsI think the crucial bit you're missing is that the fundamental disagreement boils down to whether a properly-signed-and-executed warrant ought to be sufficient for the government to get its hands on evidence or otherwise do what it needs to do to deliver justice.
To you, he seems to believe Yes, and to him, I think you seem to believe No. Historically, the answer has been Yes, and crypto has fundamentally changed that. I think crystallizing exactly why you believe the right answer is No is essential, otherwise you're just not going to convince people on that side -- in their mind, I think, you're demanding more rights than you historically had, and at the cost of protecting the rest of the population.
No, historically the vast majority of communication was not recorded, and so a warrant could not be used to access the communication. The fact of the modern world is that for the first time in history almost everything we do is recorded, and so subject to those warrants.