 Laying the Groundwork Following the death of Joshua, the Jews consulted G-d via the Urim and Tumim to see which Tribe should be the first to conquer remaining Canaanite pockets within their territory. The first role fell to the Tribe of Judah. Judah invited Simeon to join them as Simeon's cities were scattered throughout the portion of Judah. (Refer back to the Book of Joshua.)
Judah captured the Canaanite king named Adoni-Bezek and cut off his thumbs and big toes. This kind of mutilation is unprecedented in Jewish warfare, but it was Divinely mandated as an appropriate punishment. Adoni-Bezek related that he had done likewise to kings he conquered, forcing them to scavenge for scraps under his table, like dogs. Because of his confession, the Jews kept him alive and brought him back to Jerusalem.
At this time, Caleb offered his daughter Achasah as a wife to whoever could rid Hebron of its giants. This was accomplished by his half-brother Osniel. (More about him a little later on.) This is one of the cases cited by the Midrash as an example of someone making a condition that could have gone horribly wrong, but turned out okay. The conditions of Eliezer (to find a wife for Yitzchak in parshas Chayei Sarah) and Saul (to marry off his daughter in I Samuel 17) also turned out okay. Contrast these with the story of Yiftach in a few chapters - that one did NOT end well. (We'll see all the details in Chapter 11, G-d willing.) Why did G-d assist Eliezer, Saul and Caleb? They were using their conditions to make shidduchim (match-making). Yiftach wasn't, so he lacked that extra protection.
The chapter ends with a list of Tribes and the cities from where they did not expel the Canaanite nations, a fact that is about to become extremely significant. By Rabbi Jack Abramowitz Listen to the shiur from Rabbi Bini Maryles on OU Torah
Listen to the shiur from Mrs. Rebecca Belizon on Torat Imecha | 
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