Matthew Henry's Commentary
Chapter 14 Introduction:
The nine tribes and a half to have their inheritance. (1-5) Caleb obtains Hebron. (6-15)

Joshuah 14:1-5
The Israelites must occupy the new conquests. Canaan would have been subdued in vain, if it had not been inhabited. Yet every man might not go and settle where he pleased. God shall choose our inheritance for us. Let us survey our heritage of present mercy, our prospect for the land of promise, eternal in the heavens. Is God any respecter of persons? Is it not better that our place, as to earthly good or sorrow, should be determined by the infinite wisdom of our heavenly Father, than by our own ignorance? Should not those for whom the great mystery of godliness was exhibited, those whose redemption was purchased by Jesus Christ, thankfully refer their earthly concerns to his appointment?

Joshuah 14:6-15
Caleb's request is, "Give me this mountain," or Hebron, because it was formerly in God's promise to him, and he would let Israel knows how much he valued the promise. Those who live by faith value that which is given by God's promise, far above what is given by his providence only. It was now in the Anakims' possession, and Caleb would let Israel know how little he feared the enemy, and that he would encourage them to push on their conquests. Caleb answered to his name, which signifies "all heart." Hebron was settled on Caleb and his heirs, because he wholly followed the Lord God of Israel. Happy are we if we follow him. Singular piety shall be crowned with singular favour.

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