chief of the princes, the name given to the chief cup-bearer or the vizier of the Assyrian court; one of Sennacherib's messengers to Hezekiah. See the speech he delivered, in the Hebrew language, in the hearing of all the people, as he stood near the wall on the north side of the city (2Ki 18:17-37). He and the other envoys returned to their master and reported that Hezekiah and his people were obdurate, and would not submit.
i.e. "chief cupbearer" (2 Kings 18-19; Isaiah 36-37). Sent by Sennacherib with Tartan who probably had chief command (first in 2Ki 18:17; Isa 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 (Isa 8:7-8; 10:5-6): "am I now come up without the Lord to destroy it? The Lord said, Go up against this land" (2Ki 18:25). Isaiah (Isa 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 (Isa 36:16-17), pretending to have Jehovah on his side, yet classing Jehovah with the idols of other lands overthrown by Assyria (Isa 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 (Isa 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 (Isa 36:8-9); in filthy and blasphemous language he threatens to reduce them to eat their own excrement in the extremity of famine (Isa 36:12; 2Ch 32:11): a sample of the true nature of the pagan attack on Jerusalem, at once arrogant, blasphemous, and reckless of all decency.
This is a title, signifying 'chief cup-bearer,' borne by an officer who was sent by Sennacherib with the Tartan (general) and a Rab-saris to Jerusalem. He was the chief spokesman; and from the fact of his being able to speak in the Jews' language, he is supposed to have been either a proselyte or an apostate Jew. If so he may possibly have been acquainted with Isa 10:5-6, for he says, "Am I now come up without the Lord against this place to destroy it? The Lord said to me, Go up against this land and destroy it." 2Ki 18:17-37. On the other hand, he profanely classes the God of Israel with all the gods that could not protect their worshippers from his master. 2Ki 19:4,8; Isa 36:2-22; 37:4-8.
... one of the officers of the king of Assyria sent against Jerusalem in the reign of Hezekiah. [HEZEKIAH] (B.C. 713.) The English version takes Rabshakeh as the name of a person; but it is more probably the name of the office which he held at the court, that of chief cupbearer.