1)

Why does it say that that Yehudah conquered Chevron? In Sefer Yehoshua, (15:14) it says that Kalev already dispossessed the giants!

1.

Radak: It means that they already conquered it. Malbim - there it is attributed to Kalev; he was the head of Yehudah, and they followed him. Chevron itself was given to the Leviyim, Kalev received the field of (around) the city, and the Chatzeros.

Sefer: Perek: Pasuk:

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