One of the greatest journalists of the 20th century, I. F. Stone decided to study classical philosophy after he retired. The result is this best-selling book. An iconoclast is someone who intentionally destroys a religious icon. It's used figuratively to mean someone who assails the unassailable, who questions the unquestionable, and challenges those generally thought to be beyond challenge. You've probably heard that Socrates served this role in ancient Athens. He was a gadfly, hanging out in the market denouncing gods and government.
Knowing the gadfly nature of Socrates, and the gadfly nature of Stone, you might assume this book is a celebration of Socrates's life. You'd assume wrong. Stone finds in his research that Socrates (more accurately, Plato's representation of Socrates) wasn't much for liberal democracy. While Athens should never have sentenced him to death, Stone makes a case for why Socrates isn't such a great icon for progressives.
Why this is liberal/progressive: Blacklisted in 1950, I. F. Stone started his own weekly newspaper, I. F. Stone's Weekly. By diligently reading obscure government reports in the public domain, Stone was able to provide political insight unmatched by his mainstream contemporaries. When asked how he saw his role as a progressive journalist, Stone responded --
"To write the truth as I see it; to defend the weak against the strong; to fight for justice; and to seek, as best I can, to bring healing perspectives to bear on the terrible hates and fears of mankind, in the hope of someday bringing about one world, in which men will enjoy the differences of the human garden instead of killing each other over them."
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