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Noam Chomsky prob

Shoshana Zuboff

Even stuff she wrote 100 years ago legit

But her recent stuff good too

Think she was one of the first to put it succinctly

Facebook or democracy

Choice is ours

And we've made our choice

Marshall McLuhan, the media theorist.

Evgeny Morozov. His recent book To Save Everything, Click Here and earlier book The Net Delusion could be exactly what you are looking for. (I haven't read them myself, have only read reviews.)

Seconding Shoshana Zuboff also. Her latest book is The Age of Surveillance Capitalism.

Also seconding Jaron Lanier, for the books You Are Not a Gadget and Who Owns the Future?

Well, I don't know if they'd really fit the bill for you, but what comes to my mind is stuff by Jaron Lanier, and "When Google Met Wikileaks" by Julian Assange. Assange actually seems similar to Chomsky to me because of the depth and breadth of his knowledge.

The Noam Chomsky of IT