Equestria was probably when she met her match, after however long she’s spent ravaging other lands for her benefit and pleasure, and even then, she could’ve won
under some circumstances.
She’s wont to be complacent, whether she neglects to
pretend to possess kindness at least half the time (“Crackle Cosette”/Shutter Bug being a case where she improved for the most part [save blowing off Starlight]), or
she completely fails to tell her minions about a pony named “Starlight Glimmer,”
despite her being Twilight’s pupil, and Chrysalis knowing about that (per her dialogue), on top of deciding
not to replace her, and her minions not being great impersonators overall anyway. (You can tell by their dialogue none of them knew Starlight’s name… and the less said about how “Spike” and “Rainbow Dash” acted, the better, lol)
Mean Twilight was interesting in that she was an
idealized version of Chrysalis with more self-awareness and self control, and true to form, the personified vices in the form of the other five got her killed, just as Chrysalis is her own worst enemy.
Ultimately, one of the defining differences between Starlight and Chrysalis is that the former can acknowledge and learn from her mistakes.
@Philweasel
Her greatest virtue is determination. Arguably even more so than the other villains. I suspect it might be easier to break either Tirek or Cozy Glow’s spirit, than hers.
(Also she has a bit of luck on her side as well)
Unwavering determination and ambition are, in and of themselves, a very dangerous thing to be up against, and Chrysalis is no exception. The most plausible way she’d truly give up is if she’s dead, and maybe not even then.
(I think she’s like the Mojo Jojo of MLP in some ways: had an army she lost, doesn’t think everything through, intelligent, a very
persistent antagonist, credible threat, created evil knockoffs, is sadistic [albeit Mojo less so], has style up the wazoo, not
stellar at learning from mistakes… although I think Mojo Jojo is arguably a better manipulator than her [it says something that he seems to understand the Girls’ mindsets significantly more than Him, who’s all-too-often surprised that anger and fear wasn’t enough]; in the end, they’re both
definitely on my “favorites” list regarding villains, and perhaps it would be an interesting idea, seeing them interact)