He's referencing that we have early 20th and late 19th century case law about third parties holding documents, etc, that is used to make everything sitting at a cloud service subject to subpoena without a warrant (email, etc, too).
There's all kinds of precedent that was based on sane tradeoffs for the 1800's that doesn't make sense anymore with the more complicated ways we transact and interact and with the ability of technology to commit mass surveillance.
The problem has only been super significant for 15-20 years, which is a blink of an eye in this sense; not even enough time for the populace to really understand and appreciate the issue.
It is, of course, still broken.
Attitudes have changed a lot.There is an episode of Yes Minister where the minister does not want to push a shared govt database law because of privacy concerns. Another where the idea of ID cards is called political suicide. Absolutely true at the time, but the former is happening, and the latter is still not with us the UK but its no longer unacceptable to push the idea.
Kids are growing up expecting to be tracked (a lot of parents use "apps" to track what their kids do) so it will become even more normalised. People are used to being tracked as the tradeoff for map apps. There is a lot of surveillance anyway (CCTV and face recognition, number plate recognition, paying by card) so its already normal
And in this case, judicial precedent follows evolving (both popular and legal) ideas of what the words in the constitution mean.
"The right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures..."
"Persons, houses, papers, and effects" has been interpreted in terms of what things a person had, excluding things that they had given someone else to hold. It was a pretty reasonable interpretation and compromise, until it was the governing case law that covered the cloud.
Legislation can limit what Federal agents are allowed to do totally irrespectively of whether those things would separately violate the constitution.
Someone goes into politics because they want the power to run things.
Bureaucrats and agencies of the government want the power to run things for similar reasons, and it makes their jobs easier. Will the police ever say they do not want more powers to investigate crimes, or catch criminals? Will social services either? There are all kinds of things that can be better enforced with more information.
On top of all that they are part of the same cultural change that puts a lower value on individual liberties. It means politicians are a lot less inclined to refuse. There has also been a political drift to following expert advice with less scepticism, and the experts on these issues are the police, intelligence agencies, etc.
One cause close to my heart is that in the UK a number of local authorities keep hassling home educators (trying to bully them into sending their kids to school) even though their kids tend to do better than school going kids (their are studies showing better outcomes) because it seems inconceivable to them that people can do a better job than they do. I know people affected by this. A lot of them are utterly opposed to the idea that parents can make this decision at all.
So you admit they are not actually liberals and when they say they are they are incorrect.
And in any case: the law is a blunt instrument. It's (usually) better as a slowly changing representation of conventions and social consensus instead of something that we make sweeping changes in (whether legislatively or judicially).