Even as he knew his opinion was generating controversy he didn't take any steps to admit, control, or deal with it, instead he reveled in it. He knew what he was doing.
This article mentions Damore was diagnosed in his mid-20s with high-functioning autism. https://www.theguardian.com/technology/2017/nov/16/james-dam...
> He does not once, however, use his autism to excuse his actions. He is fiercely resistant to portraying himself as any kind of victim, and says he never informed Google of his autism diagnosis. “I’m not sure you’re expected to,” he says, “or how I would even do that.”
I mentioned it as a point in favor of the "naive" theory. The article also supports it:
> Damore concedes now that he “wasn’t really skilled enough to push back on anything” in some interviews. It’s frustrating, he adds, that he’s now associated with the “alt-right” when he’s “more of a centrist”. He admits he did not look too deeply into Duke’s background when the photos were taken, and asks me not to publish the image of him in a “Goolag” T-shirt with this article. “I can definitely see how it was damaging, but it was a free professional photo shoot and I wasn’t really familiar with politics then,” he says. “I was pretty busy and ignorant.”
> Was his interview with the “alt-right” personality Milo Yiannopoulos an error? “It’s hard to say,” he replies. “I don’t really know what the long-term consequences of any of my actions are.”
You can furthermore see that naivety in how quickly he ended up accepting offers and olive branches from alt-right personalities. It seemed like he wasn't aware who he ended up 'siding' with.