Glen did a great job of making arguments backed up by empirical evidence.
Curtis tried to do the same, but imo his examples were more distant and so less effective. There's big differences between the peacetime political, wartime political and corporate settings that make examples from one scenario difficult to translate to the others (namely, the type of goal of the entity and the selection function that produces them). A little too close to "concentration is efficient, it's why bees huddle together in nests and why we have cities and yimbyism, therefore it's contradictory to oppose concentration camps as a tool of government"
Glen did a good job of pointing out "you want X? Well let me tell you about actually-existing X in our current society". The critique that these examples don't count because they are a byproduct of our democratic status quo strikes me as weak; all political systems everywhere are born in a pool of inconvenient slop, your thing has to be robust to that.
Curtis was at his strongest when critiquing the status quo. The argument that NYT depends on gov info leaks which can be viewed as a (decisive) unfair subsidy was novel, at least to me, and it's compelling. Democratic politics does need to have a more honest account of the role of elites; "they're all a bug in the system" is not it, and "they're there and if you don't trust them you're a bad conspiracy theorist and a danger to public health" is also not it.
Glen's closing speech was amazing, though I think to a skeptic "I agree the US isn't a democracy, but I think we should actually become one" would not be convincing without specific compelling ideas for how that would happen. I would love to see Glen continue to flesh that out in more detail, perhaps more object-level than Plurality (eg. "how would my system decide how to solve urban crime and execute on the solution?")