10 Obscenely Evil Video Game Villain Plans

The Thalmor are almost always behind anything bad going on in Tamriel, all the way back to the original games. And at the start of Skyrim, they seem to have won via the white-gold concordat more or less throwing open the gates of every level of the Empire's government for the Thalmor to waltz right in. They have more or less defeated the empire with a single treaty.

But the Thalmor's leaders, knowing that that isn't enough to gain full control, ordered for events to be manipulated to spark a civil war in the northernmost region of Skyrim.

As you learn from a note you find in the Thalmor Embassy, Ulfric Stormcloak MIGHT be a Thalmor sleeper agent (he escaped before they could confirm that the programming took hold and, for obvious reasons, cannot get close enough to confirm) and the entire war was their idea. They want the Empire as weak as possible in order for them to conquer the whole thing, and nothing weakens a nation like a good old fashioned civil war.

As such, this brutal and costly civil war needs to go on as long as they can possibly make it, which is why the greater imperial legion hasn't come into Skyrim to help Tullius put down the rebellion. Orchestrating so much death and misery on a continental scale, in order to finally put an end to an entire culture's religion is some next-level evil stuff.