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But the angels who did this are imprisoned for the final judgment for their conduct, so what other angels would dare do it again?
but suppose He didn't get them all the first time, or last time?
Enoch only says God took Azazel and Samjaza and a few other of the leaders.
Some were still around in Christ's time, says so in the New Testament, and it's for sure Satan was on the ground, in the wilderness, because he tried to tempt Christ.
See, this is where it gets confusing.
Christ cast out some demons, "We are legion", threw them into some pigs and ran them off a cliff.
Where did they come from?
BTW a legion is roughly 4,000, by Roaman standards.
and why did they beg Christ not to cast them into the darkness?

Thank you for your reply!

Christ cast out some demons, "We are legion", threw them into some pigs and ran them off a cliff. Where did they come from?

From 1 Enoch (Charlesworth's Pseudepigrapha):

"But now the giants who are born from the (union of) the spirits and the flesh shall be called evil spirits upon the earth, because their dwelling shall be upon the earth and inside the earth. Evil spirits have come out of their bodies. Because from the day that they were created from the holy ones they became the Watchers; their first origin is the spiritual foundation. They will become evil upon the earth and shall be called evil spirits. The dwelling of the spiritual beings of heaven is heaven; but the dwellin gof the spirits of the earth, which are born upon the earth, is in the earth. The spirits of the giants oppress each other; they will corrupt, fall, be excited, and fall upon the earth and cause sorrow. They eat no food, nor become thirsty nor find obstacles. And these spirits shall rise up against the children of the people and against the women, because they have proceeded forth (from them).

"From the days of the slaughter and destruction, and the death of the giants and the spiritual beings of the spirit, and the flesh, from which they have proceeded forth, which will corrupt without incurring judgment, they will corrupt until the day of the great conclusion, until the great age is consummated, until everything is concluded (upon) the Watchers and the wicked ones. And so to the Watchers on whose behalf you have been sent to intercede - who were formerly in heaven - (say to them), 'You were (once) in heaven, but not all the mysteries (of heaven) are open to you, and you (only) know the rejected mysteries. Those ones you have broadcast to the women in the hardness of your hearts and by those mysteries the women and men multiply evil deeds upon the earth. Tell them, 'Therefore, you will have no peace!'" - Chapter 15, from verse 8 and all of Chapter 16

To sum it up, the book of Enoch tells us that the Watchers are the fallen angels, the ones who sinned, who have been chained up for the final judgment. That would be all of them. They came from heaven and were on assignment to take care of Adamic man on earth.

The children that the Watchers had with mortal women were the "giants" - who were killed. Their spirits are the evil spirits, the demons, the unclean spirits who are not allowed to leave earth because they were born here out of the unholy union of angel and mortal women.

why did they beg Christ not to cast them into the darkness?

Probably because the darkness is where their fathers, the Watchers are chained for the final judgment.