2 Kings 18:23
Now therefore, I pray thee, give pledges to my lord the king of Assyria, and I will deliver thee two thousand horses, if thou be able on thy part to set riders upon them.
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EXPOSITORY (ENGLISH BIBLE)
(23) Give pledges to.—Rather, make a compact with . . . So the Syriac; literally, mingle with . . . have dealings with (Psalm 106:35). Gesenius explains: join battle with; literally, mingle yourselves with: LXX., μίχθητε δὴ. Mr. Cheyne prefers, lay a wager with . . . The rab-sak sneers at Hezekiah’s want of cavalry, an arm in which the Assyrians were preeminently strong; and further hints that even if horses were supplied him in numbers sufficient to constitute an ordinary troop, he would not be able to muster an equivalent number of trained riders.

2 Kings 18:23-24. Now, therefore, give pledges to my lord the king — That is, give hostages to ensure thy future obedience and subjection. And I will deliver thee two thousand horses, &c. — There is so little likelihood of thy being able to withstand the power of my master, who has thousands of chariots and horses, that I challenge thee to produce two thousand skilful horsemen that know how to manage horses, and I will give thee two thousand horses for them. How then wilt thou turn away the face of one captain, &c. — How wilt thou force him to turn his back to thee, and flee away from thee?

18:17-37 Rabshakeh tries to convince the Jews, that it was to no purpose for them to stand it out. What confidence is this wherein thou trustest? It were well if sinners would submit to the force of this argument, in seeking peace with God. It is, therefore, our wisdom to yield to him, because it is in vain to contend with him: what confidence is that which those trust in who stand out against him? A great deal of art there is in this speech of Rabshakeh; but a great deal of pride, malice, falsehood, and blasphemy. Hezekiah's nobles held their peace. There is a time to keep silence, as well as a time to speak; and there are those to whom to offer any thing religious or rational, is to cast pearls before swine. Their silence made Rabshakeh yet more proud and secure. It is often best to leave such persons to rail and blaspheme; a decided expression of abhorrence is the best testimony against them. The matter must be left to the Lord, who has all hearts in his hands, committing ourselves unto him in humble submission, believing hope, and fervent prayer.The phrase translated "give pledges," or "hostages" (margin) may perhaps be best understood as meaning "make an agreement." If you will "bind yourself to find the riders" (i. e., trained horsemen), we will "bind ourselves to furnish the horses." The suggestion implied that in all Judaea there were not 2000 men accustomed to serve as cavalry. 19. Rab-shakeh said—The insolent tone he assumed appears surprising. But this boasting [2Ki 18:19-25], both as to matter and manner, his highly colored picture of his master's powers and resources, and the impossibility of Hezekiah making any effective resistance, heightened by all the arguments and figures which an Oriental imagination could suggest, has been paralleled in all, except the blasphemy, by other messages of defiance sent on similar occasions in the history of the East. Give pledges to my lord, i.e. give him hostages to secure him from thy future rebellion, and he will depart from thee. Or rather, contend with my lord in battle; seeing thou hast counsel and strength for war, do not lie lurking in thy strong hold, but come out into the open field, and let us try for mastery; and whereas thou mayest pretend thou wantest horses to fight with me, if thou wilt accept of my challenge, I will furnish thee with two thousand horses, if thou hast riders for them; as it here follows.

And the king of Assyria sent Tartan and Rabsaris, and Rabshakeh from Lachish to King Hezekiah with a great host against Jerusalem,.... Notwithstanding he took the above large sum of money of him, so false and deceitful was he: these were three generals of his army, whom he sent to besiege Jerusalem, while he continued the siege of Lachish; only Rabshakeh is mentioned in Isaiah 36:2 he being perhaps chief general, and the principal speaker; whose speech, to the end of this chapter, intended to intimidate Hezekiah, and dishearten his people, with some circumstances which attended it, are recorded word for word in Isaiah 36:1 throughout; See Gill on Isaiah 36:1 and notes on that chapter. Now therefore, I pray thee, give {i} pledges to my lord the king of Assyria, and I will deliver thee two thousand horses, if thou be able on thy part to set riders upon them.

(i) Meaning, that it was best for him to yield to the king of Assyria because his power was so small that he did not have men to care for two thousand horses.

EXEGETICAL (ORIGINAL LANGUAGES)
23. Now therefore, I pray thee, give pledges to my lord] R.V. my master. The change conforms to verses 24 and 27 below. Having ridiculed any trust in Egypt, and expressed his opinion that Hezekiah could not expect help from Jehovah, after demolishing all the altars in the land, Rab-shakeh comes to his third argument. This is, ‘you have no forces to resist us’. He puts this into the form of a taunt. The verb rendered ‘give pledges’, has in its simpler voice, the sense of ‘mortgaging’ or ‘giving something in pledge’. In the present verse it appears to mean ‘pledge yourself’, ‘put yourself under some penalty’. And so the taunt is equivalent to saying: ‘You dare not undertake to find two thousand riders, if I offer you the horses for them. If you dare, then do it. The horses are ready; I challenge you to provide the men’.

I will deliver] R.V. give. The verb is the one usually rendered ‘give’, and the insult is made the greater by this proud way of expressing superiority.

Verse 23. - Now therefore, I pray thee, give pledges to my lord the King of Assyria, and I will deliver thee two thousand horses, if thou be able on thy part to set riders upon them. "Pledge thyself," i.e. "to find the men, and I will pledge myself to find the horses." It is a strong expression of contempt for the military power of the Jews. They have not only no trained cavalry, but, were any one to furnish them with two thousand horses, they could not find the men to ride them. The Jewish army does, in fact, appear to have consisted of infantry and chariots only. 2 Kings 18:23Still less could Hezekiah rely upon his military resources. נא התערב: enter, I pray thee, (into contest) with my lord, and I will give thee 2000 horses, if thou canst set the horsemen upon them. The meaning, of course, is not that Hezekiah could not raise 2000 soldiers in all, but that he could not produce so many men who were able to fight as horsemen. "How then wilt thou turn back a single one of the smallest lieutenants of my lord?" פל את־פּני השׁיב, to repulse a person's face, means generally to turn away a person with his petition (1 Kings 2:16-17), here to repulse an assailant. אחד פּחת is one pasha; although אחד hguo, which is grammatically subordinate to פּחת, is in the construct state, that the genitives which follow may be connected (for this subordination of אחד see Ewald, 286, a.). פּחה (see at 1 Kings 10:15), lit., under-vicegerent, i.e., administrator of a province under a satrap, in military states also a subordinate officer. ותּבטח: and so (with thy military force so small) thou trustest in Egypt וגו לרכב, so far as war-chariots and horsemen are concerned.
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