I think you're reading things into it that aren't there?
As far I can tell the quote is about inevitability but not justification. The belief that strongmen will happen but no endorsement of that. Rather the opposite, I think.
Yeah, you're right. Just did a bit more research, and it appears that Codevilla isn't exactly a Trump supporter or apologist. Just a fatalistic, out-of-touch ultra-conservative who thinks the republic was screwed either way, because the masses will turn to authoritarianism rather than accept the elite's affronts to the natural order of things. What misled me was his contribution to the Claremont Institute, which tends towards apology (Flight 93 election), as well as the imagery of an ineluctable popular mass uprising against the elites which ironically reminds me of Marx. Something should also be said about his longing for an imaginary past where America truly lived up to her ideals, which fits right into Trump's MAGA rhetoric.
Regardless, the blogger herself was clearly using this quote as a justification for her political opinions. This was actually my main point: anyone can cherry-pick some intelligent-sounding pieces of rhetoric in support of their beliefs, whichever they are. In the Internet age, you will usually be able to find some decently-written essay to quote as a support ; even if you don't, you can always write and publish your own. For that matter, I'm not certain that the second quote captures the entirety of Chesterton's views on the subject matter. I don't really care, though, since he himself was so eager to trivialize the thoughts of other authors and philosophers.
It doesn't excuse the fact that I did overreach by attributing the Trumpism to the quote itself rather than the context of its use. Sorry. I'm not in the best mental state right now, and it was probably a mistake for me to come back here just to rant about someone being wrong on the Internet.