There are two parts to this: "wiretap-like" ephemeral communication, and "personal-papers-like" data stored in devices (and, more importantly in this debate, in associated cloud services).
On the far more important personal papers side, there has simply never, ever been a time in the past when you could expect as a matter of course to get somebody's personal papers surreptitiously, from a third party. Yes, you might have gotten lucky and been able to do that, but in the vast majority of cases you were going to have to go directly and overtly to that person and seize those papers.
That's a HUGE change. It's new with cloud storage and remote device access. It's total bullshit to pretend that it resembles anything in the past.
Nor is it new that the target of an investigation can obscure or obfuscate the content of those papers, or destroy those papers when you come after them, or hide them and refuse to tell you where they are, or any number of other things. People hid their letters all the time. There's nothing new in kind here.
As for matters of degree, well, yeah, modern encryption is easier and more effective than old methods of securing your papers. On the other hand, the "papers" being secured are incomparably more detailed, information-rich, and difficult to avoid creating, and you carry all of them with you all the time. What you would have gotten on somebody if you managed to find their hidden letters even 20 years ago is not even close to what you can get on somebody burrowing through their phone today.
So if there has been any change in the practical circumstances recently, it's that searches of "personal papers" have become more productive, not less. And encryption would only partially undo that.
On the less important wiretap side, yes, there have been wiretaps for about 100 years. They were pretty controversial even in those illiberal times, but they crept by the US Supreme Court (1926, I think it was). However, in the WaPo article, we had talk about "standard American practice for the past couple of hundred years".
That puts the time before wiretaps into play. And I choose to look at all of the time before wiretaps, which includes most of the time during which the common law developed, the time during which legal expectations about privacy evolved, and the time at which the US constitution was written. In the context of that time, wiretaps are a pretty damned recent blip. They were a technological windfall for spooks, and spooks' addiction to them doesn't justify perpetuating that windfall when the technology changes.
 The person who made the "last couple of hundred years" comment was admittedly not Rogers, who apparently confined himself to disingenuously advocating for technical measures he has to know can't possibly work, and which would be suspiciously amenable to exactly the sort of abuse his agency is famous for. The "couple of hundred years" comment was from deputy AG David Bitkower. So maybe I should have named Bitkower as a sack of shit, too.