Joshua 14:12

12 And now I ask of thee this mountain, as the Lord said in that day; for thou heardest this word on that day; and now the Enakim are there, cities great and strong: if then the Lord should be with me, I will utterly destroy them, as the Lord said to me.

Joshua 14:12 Meaning and Commentary

Joshua 14:12

Now therefore give me this mountain, whereof the Lord spake
in that day
The mountainous part of the country, the hill country of Judea, in which Hebron, Debir, and other cities were; for it was not one particular city only that Caleb requested, but a large tract of ground;

for thou heardest in that day how the Anakims [were] there, and [that]
the cities [were] great and fenced;
that the giants, called Anakims, dwelt in the mountainous country, and their cities, Hebron, Debir, and Anab, were very large, and well fortified; this Joshua heard at the time the spies were sent into the land, he being one of them; and this he heard, not from the report of the spies, but from the people of the country, and therefore must know that to conquer these men, and subdue their cities, was an arduous undertaking; but since he had strength and courage, he hoped his request would be granted:

if so be the Lord [will be] with me;
which he spake not as doubting of his presence and power to be with him, and assist him, but as placing his confidence therein, and, distrusting his own power and ability, having no dependence or that, but believing that the Lord, or, as the Targum, the Word of the Lord, would be with him for his help:

then,
says Caleb,

I shall be able to drive them out, as the Lord said;
that is, to drive the Anakims out of their cities, or out of the mountains, the caves and dens there, to which they betook themselves, since the taking of Hebron, Debir, and Anab, by Joshua, ( Joshua 11:22 ) ; and he relied upon the promise of God to enable him to do this, and not upon his natural strength and courage, or the number and prowess of the warlike tribe of Judah, of which he was prince.

Joshua 14:12 In-Context

10 And now the Lord has kept me alive as he said: this the forty-fifth year since the Lord spoke that word to Moses; and Israel journeyed in the wilderness; and now, behold, I this day eighty-five years old.
11 I am still strong this day, as when the Lord sent me: just so strong am I now to go out and to come in for war.
12 And now I ask of thee this mountain, as the Lord said in that day; for thou heardest this word on that day; and now the Enakim are there, cities great and strong: if then the Lord should be with me, I will utterly destroy them, as the Lord said to me.
13 And Joshua blessed him, and gave Chebron to Chaleb the son of Jephone the son of Kenez for an inheritance.
14 Therefore Chebron became the inheritance of Chaleb the of Jephone the Kenezite until this day, because he followed the commandment of the Lord God of Israel.

The Brenton translation of the Septuagint is in the public domain.