14:12a

Now therefore give me this hill country: The phrase hill country refers to a region that had mountains in it. In verses 13-15 Joshua gives the town of Hebron to Caleb. Hebron was in this mountainous area.

that the LORD promised me on that day: Numbers 14:24 tells how Yahweh promised to give Caleb the land that he had explored.

Here are some other ways to translate this phrase:

So I’m asking you for the hill country that the Lord promised me that day (Contemporary English Version)
-or-
Now give me the mountain region which Yahweh told me then I will receive

14:12b

for you yourself heard then that the Anakim were there: When the twelve spies came back, they told Moses about people called Anakim who lived in that land. Joshua was there and heard the report.

Anakim: The term Anakim refers to people who were descended from Anak. They are mentioned in Joshua 11:21, and you should translate this word the same way in both places.

Here are some other ways to translate this clause:

You heard then that the descendants of Anak lived there
-or-
At that time you heard that the Anak people lived there

14:12c

with great and fortified cities: The phrase with great and fortified cities indicates that the Anak people lived in towns with strong walls and gates.

Here are some other ways to translate this phrase:

they lived in large towns surrounded by walls
-or-
they have large walled towns

14:12d

Perhaps with the LORD’s help: The Hebrew phrase that the Berean Standard Bible has translated as Perhaps is more literally “perhaps, maybe.” This word in Hebrew expresses hope, not doubt.

Here are some other ways to translate this phrase:

if Yahweh is with me
-or-
I know that Yahweh will help me

I will drive them out: The clause I will drive them out means that Caleb will force the Anak people to leave the land and he will be able to live there himself.

Here are some other ways to translate this clause:

I will force them to leave their land
-or-
I will take their land from them

14:12e

as the LORD has spoken: Here are some other ways to translate this phrase:

as Yahweh promised
-or-
as Yahweh promised ⌊that I would do.⌋

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