Getting repeatedly beaten down by being a Sorkin style democrat eventually caused him to re-consider the entire American political system, iirc.

"Why should the best case scenario be harm reduction rather than not doing harm in the first place?"

"Why would a "democracy" that exports "democracy", often violently, not behave like a democracy with lifelong judges, electoral college and gerrymandering?"

"Why would the establishment fight Bernie and progressives with more vigor and ferocity than Republicans, who they're openly willing to compromise with?"

He started evaluating questions like that