I wanted to do a spooky villain image in honor of Nightmare Night and Halloween, but the question was which villain? Ultimately I decided, "Why be choosey?" I've seen plenty of fanfics where the spirit of Nightmare Moon returns and possesses Twilight or Celestia or some other character and then works to corrupt them, but why not take the path of least resistance and team up with someone likely to be sympathetic to your goals in the first place? I figure if the team-up gives Chrysalis a chance to feed on fear instead of namby-pamby love, then she'll never go hungry again.
I was also watching the Discord episodes the other week, and I couldn't help but notice as Twilight gets separated from all of her friends, then finds ponies who act nothing like them, and still eagerly slaps the Element of Harmony necklaces around their necks. By the end of the season, I suspect that she's much less blindly trusting, otherwise I would think that things could go badly very quickly.