User blog comment:ShawnCognitionCP/The Empire vs Stormcloaks, the most likely answer/@comment-9062114-20140611211441/@comment-9062114-20140611221645

The thing is, he knew, why wouldn't he have done it if he truly supported it?

That's probably impossible, due to the fact an army that large couldn't possibly fit on the Summerset Isles, and it doesn't make sense that would happen since the Altmer reproduce slower, due to the fact that they live longer.

How could he have seen THAT far into the future, he didn't know there was going to be a war probably.

He didn't even want power before this, the people put him on the throne and he accepted and now wants to control Skyrim in order to go against the Aldmeri Dominion, which the Empire is not doing.

Ulfric wants to fight it, he never says he's afraid to risk it. At the end he specifically says once he gets control of Skyrim he's going to take the war to the Thalmor, and Morrowind is not part of the Empire. Speak to the resisdents and officials on Solstheim.