Jephthah did not rush into battle but wisely tried to settle the Ammonites' grievance with Israel peacefully. His approach reveals his humility as well as his wisdom. Most men would have wanted to demonstrate their prowess in battle to impress the ones who had expressed confidence in them and to guarantee their future security with a victory. However, Jephthah restrained himself and appealed to the king of Ammon very logically through messengers. He initiated peace-talks rather than launching a war.
Jephthah appealed to the king of Ammon with three arguments. His point was that the Ammonites had no right to Israel's territory east of the Jordan that they were trying to obtain by force. First, he traced the history whereby this territory had come into Israel's possession showing that Ammon had no claim on Gilead (vv. 15-22). Israel had not attacked any territory held by Ammon or Moab when God's people approached the Promised Land in Moses' day. Israel had taken the land in dispute from the Amorites who had previously wrested it from the Ammonites.
Second, he emphasized the fact that Yahweh had given Israel this land. Thus it would have been wrong theologically to allow the Ammonites to take it from them (vv. 23-25).
"Even the pagans recognized that when victory was given by a deity, the victors had full right to possess that territory."221
"Jephthah's theology contains at least one serious flaw: Chemosh was not the patron deity of the Ammonites but of Moab. The divine patron of Ammon was Milkom."222
King Balak of Moab had never fought with Israel (Num. 22-24). This powerful king realized that opposing Israel in battle would be futile in view of the power of Israel's God.
Third, he appealed logically that Ammon had not tried to take the land she now claimed for 300 years. If she had a legitimate claim on it, she should have tried to secure it long ago (v. 26).
Jephthah's reference to 300 years (v. 26) is an important benchmark in biblical chronology. It had been approximately 300 years since the Israelites had defeated Sihon and captured Heshbon (in 1406 B.C.). Shortly after Jephthah spoke these words he defeated the Ammonites (v. 33; about 1106 B.C.) and ended the 18 year Ammonite oppression (10:8). The Philistine oppression of Israel began at the same time as the Ammonite oppression (10:7; in 1124 B.C.). The Philistines harassed Israel for 40 years (13:1; ca. 1124-1084 B.C.). The dates of the Philistine oppression are important because they provide a framework for the ministries of Eli and Samuel as well as Samson. This time reference along with the one in 1 Kings 6:1 indicates that the Exodus took place about 1446 B.C. rather than about 1280 B.C.223
Finally Jephthah called on Yahweh the Judge to judge who had rightful title to the land (v. 27). The Ammonite king disregarded Jephthah's message (v. 28). He obviously believed he could take Gilead in battle.