Judah's desire to enlist help from Simeon for the battle against the Canaanites could be interpreted as a lack of faith, as though Judah did not take God at his word that he would give the land into Judah’s hand. Klein’s remarks are representative of this opinion: “Yahweh tells Israel (here Judah) specifically what to do, but Israel only partially heeds Yahweh’s command: Judah immediately establishes a battle pact with his brother Simeon. Thus, from the outset, Israel exerts self-determination, evidencing automatic trust in human perception.”1
Yet the Lord did deliver the enemy into Israel’s hand; there were no negative consequences to Judah’s action not to fight alone. Furthermore, the text makes clear that the alliance was natural: it speaks of Simeon his brother.
In Joshua 19:9 the Lord allotted as the inheritance of Simeon a part of Judah’s portion of the Promised Land. And the census of Numbers 26:1–65 indicates that Simeon was the smallest tribe by far: it was a tribe of twenty-two thousand men of military age (Joshua 19:14), less than half the average of the other eleven tribes. It was then probably too small to receive an independent territory. Thus, in the Lord's allotment of the land, Simeon belonged to Judah. It makes perfect sense that they would fight together. Simeon's involvement in Judah's conquest, then, was a very good thing. Judges 1:1–36 begins in a very positive way—Judah and Simeon working together to fulfill the mandate given to them by Jehovah.
2 Chisholm adds to this: By inviting Simeon to participate in the campaign, Judah begins to exercise its God-given leadership role…. It may function as a foil in that this legitimate alliance between brothers for the purpose of accomplishing God’s will contrasts with the illegitimate alliances described later in the chapter and the book.
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3 And Judah said to Simeon his brother, “Come up with me into the territory allotted to me, that we may fight against the Canaanites. And I likewise will go with you into the territory allotted to you.” So Simeon went with him.