Caleb Requests Hebron
The initial division of the land occurs while the Israelites still have their headquarters at Gilgal (verse 6). Whether Caleb had been given more specific promises than were recorded in Numbers 14:24 Numbers 14:24But my servant Caleb, because he had another spirit with him, and has followed me fully, him will I bring into the land into where he went; and his seed shall possess it.
American King James Version×and Deuteronomy 1:36 Deuteronomy 1:36Save Caleb the son of Jephunneh; he shall see it, and to him will I give the land that he has trodden on, and to his children, because he has wholly followed the LORD.
American King James Version×(verses 9, 12), or whether he was now deciding which land he wanted, he now steps forward to claim those promises—Hebron, the burial place of Abraham, and the very land inhabited by the giants who had disturbed the other spies so much (Numbers 13:30-33 Numbers 13:30-33  And Caleb stilled the people before Moses, and said, Let us go up at once, and possess it; for we are well able to overcome it.  But the men that went up with him said, We be not able to go up against the people; for they are stronger than we.  And they brought up an evil report of the land which they had searched to the children of Israel, saying, The land, through which we have gone to search it, is a land that eats up the inhabitants thereof; and all the people that we saw in it are men of a great stature.  And there we saw the giants, the sons of Anak, which come of the giants: and we were in our own sight as grasshoppers, and so we were in their sight.
American King James Version×). Caleb was 40 years old one year after the Exodus (Joshua 14:7 Joshua 14:7Forty years old was I when Moses the servant of the LORD sent me from Kadeshbarnea to espy out the land; and I brought him word again as it was in my heart.
American King James Version×). And 45 years have passed since then, making Caleb now 85 years old (verse 10). So, since the time from the Exodus to entering the Promised Land was 40 years, six years have elapsed since the entry into the Promised Land. Even though elderly, Caleb is no more afraid of the Anakim now than he was at age 40.