Board Thread:Lore Discussion/@comment-27007772-20140611204941/@comment-10207438-20150128182423

The thalmor attacking skyrim would pretty much insure they lose, as I said they either have to start the war at once, either by going through the heart of the empire with an army, or by sailing around the continent(one side populated by enemies, the other with people that can easily be turned enemy plus a much longer voyage that includes more environmental dangers) leaving them open to attack by hammerfell and cyrodill, their best option would be to pull out and attempt to cripple the remnants of the empire.