שופטים, פרק ח׳, פסוק י״א

Gideon executes a sophisticated flanking maneuver designed to surprise and defeat a complacent enemy. Rather than taking a direct path, he advances through the territory of nomadic desert dwellers who live in tents and herd their flocks [רש״י, מצודת ציון, רד״ק, ביאור שטיינזלץ]. Commentators offer different perspectives on the exact purpose of this specific route. One approach suggests he travels this way to gather intelligence and discover the hiding places of the Midianite kings [רלב״ג, אברבנאל]. Another view emphasizes that this is a deliberate bypass meant to conceal his forces from the enemy until the very moment of the attack [רש״י, רלב״ג].

To maintain this stealth, Gideon travels east of the Israelite cities of Novah and Yogbehah. He carefully avoids entering the cities themselves, opting instead for a winding eastern path to remain undetected [רש״י]. Although his forces originally approach from the west, this deep detour allows him to circle around the Midianite camp and launch a completely unexpected strike from the east [ביאור שטיינזלץ].

Because of this careful planning, the enemy camp is caught entirely off guard. The Midianites sit in a state of false security, resting and trying to recover. Having seen no threat approaching from the west, they fail to post guards, never imagining that Gideon's forces could reach them [מצודת דוד, רלב״ג, ביאור שטיינזלץ]. To explain how a small force of only three hundred men could successfully strike such a massive and secure camp, it is noted that the entire assault takes place under the cover of darkness. Gideon and his men carry out their surprise attack through the night, returning from the battle only as the sun begins to rise [אברבנאל].