Charles Ellicott Commentary Isaiah 36:8

"Now therefore, I pray thee, give pledges to my master the king of Assyria, and I will give thee two thousand horses, if thou be able on thy part to set riders upon them." — Isaiah 36:8 (ASV)

Now, therefore, give pledges. — Better, make a wager. This would seem to be a taunt interpolated by the Rabshakeh in the midst of his official message. There was something absurd in the idea of Judah coming out as strong in its cavalry. Had they two thousand men who could manage their horses if they had them?