The one word that describes Satan, as well as any could, is proud.
Hubris led him to the conclusion that he could manage things as well as his Creator, even better, and he was more worthy of adulation too-- the ultimate narcissist. He thought this way despite being in the very presence of God and being graced with great intelligence. When you experience the Almighty as he actually is, and then come to think as Satan did, nothing remains that God could show of himself that could alter that opinion. The Devil was intractably lost as were all those angelic beings that rebelled with him.
Even apart from that rebellion, Satan cannot ever learn from his mistakes. Pride hardens the categories and seizes the mind, and dooms the prideful to endlessly repeat the same errors. Satan is a one-trick pony, forever trying to accomplish his aims by using the same means over and over again. Since the Fall, he keeps working the same tired plan in an attempt to thwart God's ultimate aim of redeeming mankind from the Fall.
In his mind, the Devil cannot conceive of an invention of his failing.
In the garden, God announced the protoevangelium, the first gospel message, in the midst of his curse upon Eve. A glimmer of hope for humanity, it spelled the Devil's doom. It was cryptic enough for the Devil not to fathom, even though I think he understood it much better than we often do. I think he grasped that it was the woman's child, not the man's, and he seemed to pick up God's subtlety in the using a collective singular noun (seed) with a singular masculine pronoun (he). That meant one particular son was in view rather than offspring in general, a point Paul was able to apply to God's promise to Abraham as well.
I'm absolutely certain that Satan picked up on this by the time the promise was reiterated in substance to Abraham. Why? Because it's revealed in his strategy of dealing with that promise--namely hijacking it. The basic outline of the plan he developed involves displacing the seed promised through Eve and Abraham (and Isaac and Jacob since they were the heirs of the promise) and undermining the place of the Jews as the seedbed. So his plan focused on substituting a seed for the seed and the destruction of the Jews as the seedbed.
Up in smoke goes the plan of God, at least in the mind of the Devil. A flawed strategy for sure, but one which the Devil's pride causes him to repeat over and over again. By the end of time, he will have tried it eight times! In the last couple of iterations he comes closer than ever to succeeding, but in the end, Christ steps in and throttles his efforts. This is what I call, the Antichrist Scheme.
In the 17th chapter of the Apocalypse, through the use of the symbolic imagery of the seven heads of the Scarlet Beast, John spells out the efforts made to ply this scheme throughout all redemption history. Up to the time of the writing of the Apocalypse, so in past history, five iterations of the scheme had been attempted. At the time of writing, effort number six was winding up. Efforts seven and eight were coming in the future (so some time after 95 AD).
The efforts all centered around dispossessing or disposing of the Jews, and then, if he got that far, offering his shill as the "God-man". The gospel promise, which was funneled through Abraham and accrued to the benefit of all mankind, had to be undermined, undone and displaced. Some schemes got farther than others, but all fail, ultimately, because of divine intervention. Six are actually recorded in scripture and attempt #8 (the last) is defeated by the physical return of the Lord Jesus Christ.
Satan's Attempts at the Antichrist Scheme
The five kings who are fallen, and the one who is:
1) Egypt under Pharaoh at the time of the Exodus (ca. 1446 BC)
This was an attempt to undermine the gospel promise by destroying the promise of land to Israel (the seedbed). If one aspect of promise is derailed, all promises are called into doubt. If one doesn't trust God's word, one can never be redeemed. So God raised up Moses and Joshua who led the people to Canaan by divine interventions and thwarted this attempt.
2) Assyria under the dynasty of Sargon II (ca. 722 BC)
The ten northern tribes of Israel (Samaria) were exiled from the promised land (seedbed) and an attempt was made to besiege Jerusalem and destroy Judah (under Sennacherib, Sargon's son). God intervened in response to Hezekiah's prayer, and Judah was delivered and stayed in the land insuring that a remnant survived to see the promise.
3) Babylon under Nebuchadnezzar (ca. 586 BC)
In his third foray into Judah in 19 years, Nebuchadnezzar destroyed Jerusalem, razed the Temple, and deported what was left of the population after the siege and two earlier deportations (605 and 597 BC). Thus, the Babylonian Captivity began; it was not ended until God intervened by appointing Cyrus to deliver the captive Jews (539 BC). Had God not sent Cyrus, the Israelites would never have returned to the promised land, and God's promise would have blown away like dust in the wind.
4) Persia under the influence its highest noble, Haman (ca. 475 BCE), which scheduled the slaughter and plunder of all the Jews. God raised up Esther for such a time as that and through her intervention turned the plot back on Haman's head;
5) Hellenistic Syria (the King of the North) under Antiochus Epiphanes (ca. 165 BCE), which attempted to eradicate Jewish practice and modeled the abomination of desolation. God intervened by giving the forces of the Maccabees a stunning, upset victory which resulted in independence for Israel and the purification of the Temple (which is celebrated today as Hanukkah). [BTW, this makes me wonder if the Maccabees shouldn't be part of the canon of scripture, as it is in the R.C.C.]
6) Rome under Vespasian (ca. 70 CE), which left no stone unturned in Jerusalem and started a policy of Jewish dispersion (culminated in 135 CE) which ultimately banned the Jews from the promised land (the Diaspora). God's intervention had already brought the promised seed, Jesus Christ, the incarnate Son of God, to earth and shifted the focus of God's redeeming work to the Gentiles, so the Devil was a pound shy and a day late.
The king who is to come for a short time, and the eighth:
The king who is to come for a short time, and the eighth:
7) Germany under Adolph Hitler (ca. 1933 CE), which systematically rounded up the Jews within it's domains and killed approximately two-thirds of them. God's intervention resulted in reestablishing Palestine as the homeland of the Jews and the resurrection of the nation of Israel.
8) The Ten Horns under the Antichrist (ca. SOON!), which will desecrate the rebuilt Temple in Jerusalem, like Antiochus Epiphanes did, and kill those who will not worship him as God and take his mark (they'll be Jews).
In his pride the Devil has attempted to one-up God over and over again, only to fail over and over again in his ultimate purpose. Even at the end of time, when he knows failure awaits him, his pride will compel him to bang his head against that wall one more time. He'll get farther than he ever did before, but end in disaster just like every time before. When one has that much pride, how can he ever learn a new trick?
In his pride the Devil has attempted to one-up God over and over again, only to fail over and over again in his ultimate purpose. Even at the end of time, when he knows failure awaits him, his pride will compel him to bang his head against that wall one more time. He'll get farther than he ever did before, but end in disaster just like every time before. When one has that much pride, how can he ever learn a new trick?