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Fausset's Bible Dictionary
i.e. "chief cupbearer" (2 Kings 18-19; Isaiah 36-37). Sent by Sennacherib with Tartan who probably had chief command (first in 2 Kings 18:17; Isaiah 20:1) of an army to induce Jerusalem by threats and promises to surrender. Spokesman for Tartan and Rabsaris. Possibly a Jewish deserter and apostate. This is favored by his familiarity with the Hebrew language, in which he addresses fluently (to the annoyance of Hezekiah's officers sent to meet him) the Jews on the wall, and with Isaiah's prophecy (Isaiah 8:7-8; Isaiah 10:5-6): "am I now come up without the Lord to destroy it? The Lord said, Go up against this land" (2 Kings 18:25). Isaiah (Isaiah 33:14) alludes to traitors, "sinners in Zion," "hypocrites."
Rabshakeh was a zealous pleader for his master, reckless of truth, glossing over the real miseries of deportation by Assyria (Isaiah 36:16-17), pretending to have Jehovah on his side, yet classing Jehovah with the idols of other lands overthrown by Assyria (Isaiah 36:18-20, liars need to have good memories), trying to rob the godly of their one only but sure trust in trouble, misrepresenting Hezekiah's faithful act in removing forbidden high places to Jehovah, as though he thereby had dishonored and so forfeited the favor of Jehovah (Isaiah 36:7), boasting of Assyria's might, as if, because Judah could not supply 2,000 riders if even Assyria supplied the horses, it were impossible the Jews could repel one of the least of Assyria's captains (Isaiah 36:8-9); in filthy and blasphemous language he threatens to reduce them to eat their own excrement in the extremity of famine (Isaiah 36:12; 2 Chronicles 32:11): a sample of the true nature of the pagan attack on Jerusalem, at once arrogant, blasphemous, and reckless of all decency.
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Fausset, Andrew R. Entry for 'Rabshakeh'. Fausset's Bible Dictionary. https://www.studylight.org/dictionaries/eng/fbd/r/rabshakeh.html. 1949.