Up to this point the Assyrian ambassador has been quoting his king, but now he speaks for himself. He shows his arrogance here by mocking Hezekiah, whom he addresses through Hezekiah’s officials. He says that even if Assyria were to give Judah 2,000 horses, Hezekiah would not be able to find the horsemen to ride them. So Assyria’s cavalry would still be able to defeat Judah. This is the traditional understanding of the verse. However, it is also possible that the ambassador is inviting Hezekiah to make a deal with Assyria. He suggests that if Hezekiah were to withdraw from the rebellion, Assyria would give him 2,000 horses, as long as he could provide riders for them. In this second view the offer of horses is an incentive for Hezekiah to surrender.
Since the Assyrian king is no longer speaking here, but his ambassador, it would be helpful to add a quote frame at the beginning of this verse to indicate this; for example, “Then the ambassador said to Hezekiah through his representatives.”
Come now, make a wager with my master the king of Assyria: These are words of invitation. Come now is literally “And now.” These words mark a shift in topic, away from the previous reference to Hezekiah’s policies. Many languages will need to mark this topic shift in some way. The Hebrew verb rendered make a wager comes from a root meaning “make a pledge,” “make a bargain/deal,” or even “make an agreement.” The Hebrew verb form here is a reflexive imperative, meaning “pledge yourself.” This is either a mocking taunt or a challenge (see the comments above), addressed to Hezekiah through his officials to accept an offer from the Assyrian king. As he mocks Hezekiah, he uses the Hebrew particle of entreaty, which Nouvelle Bible Segond renders “I pray you.” Most versions omit it in this context. The Assyrian ambassador refers to his king as my master. Those meeting here are the representatives of two kings; they could make a deal on behalf of their respective masters. Good News Translation renders the first half of this verse as though it is the Assyrian ambassador who is making a deal. This is not strictly correct since the Hebrew text calls on Hezekiah to make a deal (to provide horsemen). New International Version translates it more accurately with “Come now, make a bargain with my master, the king of Assyria.”
I will give you two thousand horses, if you are able on your part to set riders upon them: This is the deal the Assyrian ambassador offers to Hezekiah. If Hezekiah can find two thousand men who can ride horses, then he will give him two thousand horses. As noted above, he probably says this to mock Hezekiah, because he believes Hezekiah does not have that many horsemen. However, since the days of Solomon the Israelites had used horses in war (see 1 Kgs 4.26; see also the comments on 2.7). I will give you two thousand horses may be rendered “We will give you two thousand horses,” since the Assyrian ambassador is speaking on behalf of his king. If you are able on your part to set riders upon them may be translated “but you will not be able to find any riders for them” to express the implied meaning here.
Some translation examples for this verse are:
• Then the ambassador said to Hezekiah through his representatives, “How about making a deal with my master the king of Assyria! We will give you two thousand horses if you can find [or, if you agree to find] riders for them.
• Then the ambassador said, “Come now, make an agreement with my master the Assyrian king. We will give you two thousand horses if you have anyone who can ride them!
Quoted with permission from Ogden, Graham S. and Sterk, Jan. A Handbook on Isaiah. (UBS Helps for Translators). New York: UBS, 2011. For this and other handbooks for translators see here .