The transition from the era of conquest to the division of the land is deeply connected to the ancient history of Hebron and the extraordinary bravery of Caleb. Historically, Hebron was known as a city associated with the number four, an ancient title rooted in the physical reality of the giants who once lived there [מצודת ציון, מלבי״ם]. The primary approach among commentators is to view this title literally. According to the simplest understanding, it refers to the founding giant of the city, who was the father of three famously large sons [רש״י, רד״ק, מצודת דוד, שטיינזלץ]. Alternatively, the name reflects the total count of these four towering figures ruling together [רש״י, אברבנאל]. Other perspectives suggest the founding giant was so immense that his individual height and strength were equal to four regular men combined [אברבנאל], or that his enduring power in old age alone matched the strength of all four giants [אלשיך].
Beyond the literal giants, a deeper tradition identifies the greatest man of this city not as a physical giant, but as Abraham. In this view, the number four alludes to the four founding couples buried in Hebron's Cave of Machpelah, which Abraham purchased: Adam and Eve, Abraham and Sarah, Isaac and Rebecca, and Jacob and Leah. Abraham's spiritual greatness far surpassed the physical might of the local inhabitants. It was ultimately the merit of Abraham that stood by Caleb, helping him weaken the giants' power and successfully conquer the city [אלשיך].
Following seven years of intense conquest, the local nations finally surrendered, bringing a period of quiet that allowed the Israelites to divide their new territories [רש״י, שטיינזלץ]. Chronologically, Caleb actually asked to fight for Hebron while the wars were still raging, but the event is recorded at this juncture to bridge the narrative of the battles with the upcoming division of the land [מצודת דוד, אברבנאל].
Observers differ on how to view this ensuing peace. For some, the quiet serves to highlight Caleb's rare courage. At a time when the rest of the nation was comfortably resting from conflict, Caleb voluntarily initiated a fierce battle against giants, succeeding because God cast a divine terror upon his enemies [אלשיך, אברבנאל]. Conversely, others view this quiet as a negative outcome, arguing that the peace merely stemmed from the Israelites' laziness and failure to drive out the remaining inhabitants [רד״ק]. Finally, another tradition links this peace back to Abraham, suggesting that the forty years of quiet the Israelites previously enjoyed in the desert was a direct reward for the respect the giants of Hebron had once shown to the patriarch [רש״י].