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Judges 11:26

While Israel lived in Heshbon and its towns, and in Aroer and its towns, and in all the cities that are along by the side of the Arnon, three hundred years; why didn’t you recover them within that time?
Judges 11:26, World English Bible
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What does Judges 11:26 mean?

Jephthah is making a historical argument to the king of Ammon, essentially saying: "If this land was really yours, why didn't you fight to take it back during all the centuries that Israel has lived here peacefully?" He's pointing out that long possession and peaceful occupation suggest legitimate claim to the territory. The "three hundred years" refers to the span from Israel's conquest of Canaan through the judges period. Jephthah uses this passage of time as evidence that Ammon had plenty of opportunity to challenge Israel's control if they truly had a rightful claim. It's a reasonable-sounding diplomatic argument, though it's worth noting that Jephthah is trying to avoid war and may be stretching the facts to make his point sound stronger. Sometimes we all try to use logic and history to support our position, even when the actual situation is more complicated than we admit.