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Sennacherib and his mouthpiece, the Rabshakeh, are both classic, big-mouthed bad guys. Apparently, they never heard that "pride comes before the fall."
Sennacherib sweeps into Judah, besieging Jerusalem and boasting about how he's defeated the gods of other countries. However, his boasting has an oddly contradictory angle to it. He says God won't help the people of Judah, because it was God who ordered Sennacherib to invade (which, as God sort of says, is basically true). But at the same time, he thinks he can defeat Israel's God in combat and says that there's no point in turning to God.
Of course, God ultimately punishes him for his rather confused arrogance. The angel of destruction kills 180,000 Assyrian troops, and Sennacherib runs back home, where his sons conspire and assassinate him.