“So now give me.” Caleb expected, and asked for, the land that he was due as a reward for his faithful service to God. Caleb sets a wonderful example for believers, who should expect a reward for their faithfulness and good works, and should not be embarrassed about it as if that was somehow greedy or unloving. It is God’s good pleasure to reward those who serve Him (cp. Matt. 5:12; 2 Cor. 5:10; Col. 3:23-24).
“the Anakim.” The Anakim were descendants of Anak, who was one of the Nephilim (Num. 13:33), and thus they were related to the Rephaim, the descendants of Rapha (cp. Deut. 2:11. See also 2 Sam. 21:16, 18, 20, 22).
“It may be that Yahweh will be with me and I will drive them out.” The book of Joshua says that Hebron had already been conquered. Caleb seems here to be recalling what he and Moses said at the time of the spying out of the land. Caleb and his nephew are described as conquering Hebron in Joshua 15:13-19, but he certainly would have been in the war against Hebron in Joshua 10:36-37. This also explains how it can be that the land had rest (Josh 11:23 and Josh. 14:15). Most commentators think that Caleb is saying that Hebron has not yet been fully conquered, but that does not seem to be the case, especially in light of Joshua 14:15, which says the land had rest from war. If Caleb still had to conquer Hebron, that verse would not be accurate.