The Gulag Archipelago
Good choice!
“The Gulag Archipelago” is good. “We the Living” by Ayn Rand
My first instinct would have been the shorter “A Day in the Life of Ivan Denisovich” — that really captured what the reality of Communism was all about. If this person wants something closer to home, how about “Witness”?
The problem with attacking communism politically is that people are stubborn. They will always have wiggle room to say “well, that was just the Soviet Union, if the right people had been in charge blah blah blah.”
Communism began as economics. As economics showed that communism wouldn’t work, it became a purely political movement. Attack communism from an economic angle—the calculation problem. Communism could have the kindest, wisest, and most well-intentioned people in charge and it would still fail *for economic reasons*. Begin with basic econ so they can understand, then bring on Hayekian price theory to deliver the crushing blow.
Economics in One Lesson by Hazlitt.
Basic Economics by Sowell
Economics for Dummies
Naked Economics (not my fave but it is easy for laypeople to read and get started with)
Then move onto Capitalism and Freedom and the Road to Serfdom.