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Eric Flint is fairly outspoken about his political views (in bumper sticker terms, he's a self-proclaimed socialist, although - as is the case with most real humans - it's a bit more nuanced than that once you dig into details).

Did Flint ever elaborate on how his political outlook reflected in his works, especially 1632/Ring of Fire series?

I'm looking specifically for Flint's self-assessment in this question.

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Yes, but not in great detail.

The best I've been able to find is this interview with Eric Flint, where he says (emphasis mine):

The image people have of Germany is a Germany that was created out of the Thirty Years War and the outcome of it. But the Germany prior to the early years of the Thirty Years War is a very, very different place. It was very dynamic. It was quite democratic in many respects. It was the intellectual center of Europe and it was hammered flat by the Thirty Years War.

[...] I wanted the trade union, which is, in this case, United Mine Workers, to be a central and important part of the story because that almost never happens in modern, certainly in science fiction.

And what I wanted to use the novel for was to depict what I think are important features of democracy and egalitarianism that people today tend to take for granted. They don’t tend to think much about it. But I wanted to show how that would unfold in this utterly chaotic situation. And the final factor is that the world of Europe in the early 17th century, this is not a medieval world. We have entered the modern era. It’s usually called the early modern era. Contemporaries alive at the time were Galileo, Rene Descartes.

And from another interview:

I mostly wrote that book because I felt that Americans tend to take democracy and the principles of liberty, equality, fraternity for granted. I wanted to take a group of people raised that way, and put them into the worst war in European history, and see how it all unfolded.

Now this is all pretty vague, but we can tell a few things at least: Flint's views on democracy, and how it's perceived and enacted in different locations and eras, played a big part in the conception of the idea for his 1632 series. The fact that he wanted a trade union to be at the centre of the story is very probably also linked to his own background, having "spent about 25 years of [his] life as a political organizer in the trade unions", which in turn connects to his political views on workers' power.

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