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 God's promise is derailed, all promises are called into doubt. God may call his Son from Egypt, but if one doesn't trust God's word of promise, 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 BC)
Though a "champion" of Israel under Cyrus and other emperors who followed, under Xerxes (Ahasuerus, and particularly his prime minister, Haman) Persia became a murderous foe of the Jews. Haman scheduled the slaughter and plunder of all the Jews throughout the empire and the hanging of his archrival, Mordecai. God raised up Esther for such a time as that and through her intervention and God's favor, turned the plot back on Haman's head. If Haman had been successful, there would have been no Jews left to receive God's promise
5) Seleucid Empire under Antiochus Epiphanes (ca. 165 BC)
Dubbbed, "the King of the North" by Daniel, under Antiochus, this kingdom attempted to eradicate Jewish customs, to destroy all the Bibles (scrolls) it could, and modeled the abomination of desolation which the Antichrist will replicate in the Great Tribulation. God intervened by granting the forces of the Maccabees a stunning, upset victory which resulted in the purification of the Temple (which is celebrated in Hanukkah), and eventually, independence for Israel (after 40 years of war). Antiochus sought the complete assimilation of the Jews into his Greek, pagan Empire which would have destroyed the seedbed Messiah was to be planted in.
6) Rome under Tiberius, Vespasian and Hadrian (ca. 33-135 AD)
The Messiah, the promised seed, began proclaiming his gospel of salvation during the reign of Tiberius. Satan had unsuccessfully tried to kill Jesus as an infant through Herod's demented decree to slaughter the innocents. He would continue to press that effort during Jesus' ministry, apparently succeeding through the betrayal of Judas and the sentence of Roman Procurator, Pilate. Killing the seed would definitely destroy the promise and open the way for the Devil to accomplish his aims, but God raised Christ from the dead and overturned Satan's plan.
When the forces of Roman General Titus (under Emperor Vespasian) finally broke into the besieged city in 70 AD, no stone was left unturned in Jerusalem. The Temple was utterly destroyed, the city was left an uninhabitable ruin. It forced a depopulation of the city by the Jews for some time, but in 135 AD, after another rebellion by the Jews against Rome (Emperor Hadrian), Jews were banned by law from the environs of Jerusalem all together. Thus they became another part of the Diaspora. Perhaps this seems irrelevant in light of Jesus' death and resurrection, but that still left the unbelieving Jews bereft of promise, and all Jews without a homeland.
God's promises get fulfilled, or the one who promised them isn't God-- he's either too powerless to be God, or too unrighteousness.
God's intervention had already delivered the promised seed (Jesus), which provided redemption to all who believe on him. With that, one might suppose that the Devil was a pound shy and a day late in his efforts, but sin and death have continued on since then, and the Devil still roams about seeking someone to devour. Why? Because nothing is complete without the Jews. Though the focus of God's redemptive work shifted to the Gentiles after the Jews' rejection of Christ, undermining the promise of land still holds the potential of taking the promise of the seed with it in the minds of humans who still need to believe in Messiah in order to be saved.
The king who is to come for a short time, and the eighth:
7) Germany under Adolph Hitler (ca. 1933 AD)
Apart from world domination, Hitler's aim was to eradicate the Jews, once and for all. He had them systematically rounded up within his domains (which was where most Jews lived at the time) and killed approximately two-thirds of them. The unseen hand of God guided the situation into the defeat of the Nazis and set off a migration, unexpected by the world, of Jews to their ancient homeland in Palestine. The end result was resurrection of the nation of Israel in May, 1948.
After the failure of seven schemes, the Devil actually found himself in the worst situation ever, with Israel reestablished and the gospel reaching into all the world, EVEN AMONGST THE JEWS! He has one more flare to fire, and it will be the one that gives him the greatest whiff of victory but then suddenly delivers the most crushing defeat.
8) The Ten Horns under the Antichrist (ca. SOON!)
After the cataclysms of the Epic of Magog and the Sixth Seal, the Antichrist will step into the vacuum created by them and establish his hegemony over ten nations in his region. He will sign a treaty with Israel establishing peaceful relations for seven years and which grants Israel the right to rebuild the Temple in Jerusalem.
As the Temple is nearing completion,* and similar to Antiochus Epiphanes before him, he will enter the Temple, curtail expected activities, install his False Prophet as high priest and idol of himself as the object of worship, and kill those (they'll be Jews) who refuse to worship him as God and take his mark of submission. He will be defeated and destroyed by the Return of Christ.
In his pride the Devil has attempted to one-up God over and over again, only to fail over and over again to achieve his ultimate aim. 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, nonetheless, in dismal failure just like every time before.
*Since the only acceptable sacrifice before God (the Lord Jesus Christ) has already been offered and received, and that sacrifice was so perfect in its qualities that one offering was sufficient for all time for all people, I do not expect that God will allow any sacrifice of a lesser, and at best presaging nature, to be offered in his name again.
