What is the baddest, most evil thing Satan/Lucifer/the devil has ever done in the Bible?

[muriel_volestrangler]

175. Since this doesn't seem to have been covered, Satan is in the apocryphal books too

In the Book of Wisdom, the devil is represented as the one who brought death into the world.[8] The Second Book of Enoch contains references to a Watcher angel called Satanael,[9] describing him as the prince of the Grigori who was cast out of heaven[10] and an evil spirit who knew the difference between what was "righteous" and "sinful".[11] A similar story is found in 1 Enoch; however, in that book, the leader of the Grigori is called Semjâzâ. In the apocryphal literature, Satan rules over a host of angels.[12] Mastema, who induced God to test Abraham through the sacrifice of Isaac, is identical with Satan in both name and nature.[13] The Book of Enoch contains references to Sathariel, thought also to be Sataniel and Satan'el. The similar spellings mirror that of his angelic brethren Michael, Raphael, Uriel and Gabriel, previous to his expulsion from Heaven.

http://en.wikipedia.org/wiki/Devil#Apocrypha.2FDeuterocanon

In the second section (chapters 22-37) Enoch, now guided by Gabriel, is allowed to enter in the seventh heaven where he sees the Lord face to face. Afterwards he is anointed by Michael and becomes similar in appearance to the angels. God tests the obedience of his angels by having them bow down before Enoch. A group of angels refuse. This group is identified as the angels of Satanail. They are imprisoned, eventually the imprisoned angels bow before Enoch addressing him as “a man of God.” The story seem similar to the War in Heaven between God and Satan.[17] The Lord asks the angel Vereviel to dictate to Enoch 360 books containing all that is knowable. Later, the Lord himself tells to Enoch the secrets of the creation up to the flood, which are unknown even to the angels. Enoch is finally sent back on the earth for thirty days.

http://en.wikipedia.org/wiki/2_Enoch

Various aspects of Christianity have taken things from the grey area of the Apocrypha. That 'War in Heaven' reference is to Revelation 12; whether Revelation is intended as a description of what had already happened, of a prediction of what would happen in some future, or whether the author was in no fit state to tell the difference, is up to the reader. But that could be taken either as saying the Devil has already been cast out of heaven for rebelling; or that the Devil is still in heaven, and won't get cast out until the Apocalypse.