Okay, we have two demons here, and they know who Jesus is. First they know they will be tormented by, in their opinion, Jesus. Evil entities do not want good forced upon them. To them that is torture or torment.I thought I would challenge everyone to give their thoughts as to why God would tell Jesus to allow the demons to enter the herd of swine?
God bless
Mat 8:28 — Mat 8:32
And when he was come to the other side into the country of the Gergesenes, there met him two possessed with devils, coming out of the tombs, exceeding fierce, so that no man might pass by that way. And, behold, they cried out, saying, What have we to do with thee, Jesus, thou Son of God? art thou come hither to torment us before the time? And there was a good way off from them an herd of many swine feeding. So the devils besought him, saying, If thou cast us out, suffer us to go away into the herd of swine. And he said unto them, Go. And when they were come out, they went into the herd of swine: and, behold, the whole herd of swine ran violently down a steep place into the sea, and perished in the waters.
Second, knowing Jesus is likely to cast them out, they desire to be allowed to enter into the swine. Why? Was that preferable to being cast out into nothingness? Apparently so. The question then is- What would happen to them if they were not allowed to enter the swine? Was it their intention to cause the swine to jump into the water? Did they want to make pigs fly??? Maybe they did not want sent to the "everlasting chains under darkness for the judgment of the great day". Kinda like, "Jesus, we won't hurt anybody else, just let us go into the swine."
Jesus may have said ok knowing the swine would carry them off into the water to send them to their prison. Just as the angels who left their "estate" to cause all that trouble with the daughters of mankind which brought about the need for the Flood of Noah's time. In this case, drowning these fallen angel demons is how God sends them off to their prison chains.