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Jos 14:1 These are the inheritances which the children of Israel took in the land of Canaan, which Eleazar the priest, Joshua the son of Nun, and the heads of the fathers’ houses of the tribes of the children of Israel, distributed to them-
"Distributed" is s.w. "inheritance" or "inherit", and also "possessed". I have noted elsewhere the difference between Joshua slaying the kings, and Israel possessing or inheriting the land- which they generally failed to do. But here we read that Joshua also 'inherited' it to them. So much was done for them. We note too the king-priest association, again looking ahead to the work and dual office of the Lord Jesus.

Jos 14:2 by the lot of their inheritance, as Yahweh commanded by Moses, for the nine tribes, and for the half-tribe-
See on :5. Joshua was very good at obedience to clear commandments (Josh. 4:10,17; 8:27; 10:40). But when he had to articulate his faith in God in unexpected situations, e.g. when the ambassadors from Gibeon arrived, or when the first attack on Ai failed, he seems to have performed poorly. Legalistic obedience is no use in those cases when principles need to be applied. Josh. 5:13,14 can be read as a rebuke of Joshua, wanting to boil everything down to black and white, wanting to see God as either personally for him or against him; when the essence is to seek to discern and do God’s will. He very strictly adhered to God’s commandments with legalistic obedience, e.g., about how to approach and deal with Jericho, or how to cross the flooded Jordan and build an altar; and time and again, we read in Joshua of how he strictly relayed and obeyed the Divine commandments given by Moses (Josh. 8:31,33,35; 11:12,15,20; 14:2,5; 17:4; 21:2,8).  Yet as with any literalistic or legally minded person, it was hard for Joshua to apply the principles behind the laws to situations which weren’t specifically addressed by Divine revelation, where legalistic obedience wasn't what was required.

Jos 14:3 For Moses had given the inheritance of the two tribes and the half-tribe beyond the Jordan; but to the Levites he gave no inheritance among them-
The Levites had no material inheritance because "the sacrifices of Yahweh the God of Israel... are his inheritance... Yahweh God of Israel was their inheritance" (Josh. 13:14,33; Num. 18:20; Dt. 10:9; 18:2). Notice how "Yahweh" is put for what is sacrificed to Him. His very existence is an imperative to sacrifice to Him, despising all material advantage in doing so. Job comments that to make gold our hope and wealth our confidence is to deny “the God that is above” (Job 31:24,28). To trust in material wealth is effectively to proclaim ourselves atheists. We are described as the new priesthood (1 Pet. 2:5), so all that was true for the Levites becomes true for us. We are not to seek material inheritance. God will provide for us in ways other than our possessing land and leaving an inheritance to our children. The wonder of serving Him is to more than compensate for this.

Jos 14:4 For the children of Joseph were two tribes, Manasseh and Ephraim: and they gave no portion to the Levites in the land, except towns to dwell in, with their suburbs for their livestock and for their property-
The idea is that the number 12 was significant to God, and therefore to replace the tribe of Levi, the tribe of Joseph was split into two tribes.

Jos 14:5 The children of Israel did as Yahweh commanded Moses, and they divided the land-
The division by lot (:2) presumably meant that the tribal areas were defined and then distributed by lot. And then within those areas, each family was given a specific inheritance.

Jos 14:6 Then the children of Judah drew near to Joshua in Gilgal. Caleb the son of Jephunneh the Kenizzite said to him, You know the thing that Yahweh spoke to Moses the man of God concerning me and concerning you in Kadesh Barnea-
Caleb was head of a household within the tribe of Judah. It could be argued that he was directly related to Judah through Hezron and Pharez (1 Chron. 2:5,18,25). But "Kenizzite" (also Num. 32:12) could refer to the Gentile tribe of Gen. 15:19; or to a man called Kenaz, memorialized by Caleb naming his son with that same name (1 Chron. 4:15). And Jud. 1:13 could mean that Caleb's father was called Kenaz. Caleb means "dog", and this is apparently alluded to when he is commended for faithfully following Yahweh, as a dog would follow its master (:8; Num. 14:24). The genealogies are constructed in such a way that they don't preclude Caleb having been a Gentile who was fully accepted into the tribe of Judah.  

Jos 14:7 I was forty years old when Moses the servant of Yahweh sent me from Kadesh Barnea to spy out the land. I brought him word again as it was in my heart-
We love Caleb for this. He as utterly persuaded, as he beheld the high walled cities, that it was absolutely possible for Israel to take the land- with God's help. LXX "I returned him an answer according to his mind" suggests that his mind / heart and that of Moses were united; they were both equally confident the land could be taken. But their heart / mind is contrasted with that of the people (:8). It was all a matter of the mind, and we see again the huge importance which the Bible attaches to the heart, spiritual mindedness.

Jos 14:8 Nevertheless, my brothers who went up with me made the heart of the people melt-
Yet the same phrase is used by Rahab of how the hearts of the Canaanites melted at this time. They were both scared silly about each other. The apparently insuperable obstacles to inheriting the Kingdom were shown to be nothing at all- if approached in faith.

But I wholly followed Yahweh my God-
See on :6. Joshua and Caleb were earlier characterized by the comment that they “wholly followed the Lord” when they went to spy out Canaan (Num. 14:24; 32:11,12; Dt. 1:36; Josh. 14:8,9,14), and urged Israel to go up and inherit it. This refers to the way that the Angel had gone ahead of them, and they faithfully followed where the Angel had gone, and believed that Israel could follow that Angel wherever it led. When Israel finally did go into the land, they were told that Joshua would ‘go before’ them, and they were to follow him and thereby inherit the land (Dt. 31:3). From this we see that circumstances repeat in our lives. As Joshua had been told to be strong and of good courage in order to take the land, so he had to tell others (Josh. 10:25). As God charged him to be courageous and obedient to the book of the Law, so Joshua on his deathbed charged his people (Josh. 1:7,8 cp. 23:6). Joshua had faithfully followed, and now he became the leader who was to be faithfully followed. Likewise, he led the Israelites in battle whilst Moses stood on the hill with arms uplifted in prayer for his success. And in capturing Ai, it was Joshua’s turn to stand on a hill with arms uplifted [also in prayer?] whilst Israel fought. However, Joshua seems to have somehow gotten out of synch with the Angel when he meets Him in Josh. 5:14 and asks Him whether He is for or against Israel. We must walk in step with the Spirit / Angel in our lives; and yet no matter how much we’ve walked in step with Him, we can always allow pressure of circumstances to let us fall out of step with Him.   

Jos 14:9 Moses swore on that day saying, ‘Surely the land where you walked shall be an inheritance to you and to your children forever, because you have wholly followed Yahweh my God’-
But "forever" was conditional. For Hebron was in due course to be captured by Gentile powers. Just as the promise of eternity for us is conditional. 

Jos 14:10 Now, behold, Yahweh has kept me alive as He spoke these forty-five years, from the time that Yahweh spoke this word to Moses, while Israel walked in the wilderness. Now, behold, I am eighty-five years old today-
Comparing with :7, Joshua is saying that at this point, he has been subduing Canaan for a period of five to seven years [if we include parts of years as a year, as was the Hebrew style of reckoning, or if we consider the wilderness journeys to have been 38 and not 40 years]. This was the "long time" of Josh. 11:18.

Jos 14:11 As yet I am as strong today as I was in the day that Moses sent me: as my strength was then, even so is my strength now for war, to go out and to come in-
Caleb is confident that he is still strong enough to fight the Canaanites living in Hebron and secure it. We might prefer however if he had spoken more of God's blessing than of taking the inheritance in his own strength. The first word for "strong" is different to that translated "strength". It seems to refer to mental strength and the determination of faith. And it was this which gave him his physical strength.

Joshua appears to have been only one of a group of Moses' "young men", who moved around the camp running his errands (Ex. 24:5; Num. 11:27,28); as a similar group did for Nehemiah and Paul years later. The young men of the New Testament were also characterized by their love of the word (1 Jn. 2:14). Moses would have had a special fondness for this generation who were to enter the land. A large part of the Law was concerned with Israel's behaviour after they had settled in the land; these would only have been relevant to that younger generation. It is fitting that both Moses and Caleb (and Joshua?) maintained their youthful vigour right up to their death (Dt. 34:7; Josh. 14:11).  

Jos 14:12 Now therefore give me this hill country, of which Yahweh spoke in that day-
Although not recorded in Num. 14:24; Dt. 1:36, it appears Caleb was specifically promised Hebron at that time. Caleb had explored that area as a spy (Num. 13:22) and taken a special liking to it. We see therefore his spiritual ambition; 'this shall one day be mine'. And we can do the same, as we in this life spy out our future inheritance.  

For you heard in that day how the Anakim were there, and great and fortified cities-
Caleb seems to have wanted to make a point; that even the fortified mountain lair of the giants could be taken, even by an 85 year old. See on :15.

It will surely be that Yahweh will be with me and I shall drive them out, as Yahweh spoke-
"Drive them out" is s.w. "possess"; see on Josh. 13:1. Examples of spiritual ambition are inspirational; just as soldiers inspire each other by their acts of bravery. Achsah followed her father Caleb’s spiritual ambition in specifically asking for an inheritance in the Kingdom (Josh. 14:12; 15:18); and this in turn inspired another woman to ask for an inheritance soon afterwards (Josh. 17:4). And so it ought to be in any healthy congregation of believers. Ponder the parallel between Is. 51:1 and 7: “Hearken to me, ye that follow after righteousness, ye that seek the Lord…hearken unto me, ye that know righteousness”. To know God’s righteousness is to seek / follow it; of itself, it inspires us to ambitiously seeking to attain it.

Caleb was a Gentile who became adopted into the tribe of Judah and became a leader of the tribe. Yet he was graciously given an inheritance in the land of Israel. By his spiritual ambition, he was granted Hebron as his inheritance. He went up there and drove out the tribes with a faithful zeal unmatched in Israel. And yet, he gave away that city- for Hebron became a priestly city for the Levites to live in. He gave his place in the Kingdom to others (Josh. 14:12)- that was the level of love this great man reached.

 Jos 14:13 Joshua blessed him; and he gave Hebron to Caleb the son of Jephunneh for an inheritance-
On one level, we can quite rightly ask for material blessing, and the Father is pleased that we should. But there is a higher level we can live on, where requesting physical blessings doesn't figure so largely. We can be like Caleb, who conquered Hebron (his part in the Kingdom) for himself and then gave it to others (Josh. 14:12-14; 21:11). Many mature brethren realize that their prayers place decreasing emphasis on requesting physical blessing from God; be it safe-keeping, health etc.

Jos 14:14 Therefore Hebron became the inheritance of Caleb the son of Jephunneh the Kenizzite to this day; because he wholly followed Yahweh the God of Israel-
He zealously followed the Angel which went before him, and therefore he obtained his inheritance which in prospect the Angel had prepared for him.

I would consider the book of Joshua to have largely been written by Joshua, under Divine inspiration, although edited [again under Divine inspiration] for the exiles. And the book of Judges likewise. For the exiles too were set to reestablish God's Kingdom in the land and to inherit it again as the Israelites first did. The phrase "to this day" occurs several times in Joshua / Judges, and appears to have different points of historical reference (Josh. 4:9; 5:9; 6:25; 7:26; 8:28,29; 9:27; 10:27; 13:13; 14:14; 15:63; 16:10; 22:3; 23:8,9; Jud. 1:26; 6:24; 10:4; 15:19; 18:12). I would explain this by saying that the book was edited a number of times and the remains of those edits remain in the text. For God's word is living and made relevant by Him to every generation.

Jos 14:15 Now the name of Hebron before was Kiriath Arba, after the greatest man among the Anakim. The land had rest from war-
As noted on the force of "For..." in :12, Caleb seems to have wanted to make a point; that even the fortified mountain lair of the giants, even the greatest giant, could be taken- even by an 85 year old.