I would agree with you if "Frenemies" didn't happen. It showed that Chrysalis' titanic ego can be tempered and she is capable of forming genuine bonds with others — remember that at the end of the episode the trio were this close to touching the magic of friendship all by themselves. If the writers had carried on that theme of real friendship developing between the three instead of just kind of forgetting about it and keeping them as "egotistical villains out to conquer the world for themselves but now they're standing next to each other" then I think it would have been possible to redeem Chrysalis in a natural sort of way.BUT it would require Grogar to actually have been Grogar instead of Discord in disguise (which is stupid for a whole host of other reasons that would completely derail this post). Having a common enemy in the ponies allowed Chrysalis to bond with the other villains, so the most logical way to open the door for a 'true' redemption would be for the villains and the ponies to have a common enemy as well — Grogar. As a very rough idea, the villain's plan to betray Grogar goes wrong and he ends up with his bell, perhaps after Discord and one of the Princesses have been knocked out of the fight. Neither the ponies or the villains are strong enough to beat bell-powered Grogar on their own, so they're forced to put aside their differences and work together to defeat him. At several points during the final battle the ponies save the villains and the villains save the ponies, etc. and once it's all said and done the ponies extend the hoof of friendship, which is very tentatively accepted in a "I guess we won't try to kill you any more but we're not friends okay" sort of way. Then in the finale with its time skip the trio can be shown again, reformed and still working together amongst the ponies in some amusing manner.Unfortunately the writers seem to have been very lazy when it came to wrapping up the show and ended up retreading the same villain battle we've been seeing over and over for nine whole years now instead of trying to do something different.