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Judges 11:19

ESV Israel then sent messengers to Sihon king of the Amorites, king of Heshbon, and Israel said to him, ‘Please let us pass through your land to our country,’
NIV Then Israel sent messengers to Sihon king of the Amorites, who ruled in Heshbon, and said to him, 'Let us pass through your country to our own place.'
NASB And Israel sent messengers to Sihon king of the Amorites, the king of Heshbon; and Israel said to him, 'Please let us pass through your land to our place.'
CSB "Then Israel sent messengers to Sihon king of the Amorites, king of Heshbon. Israel said to him, 'Please let us travel through your land to our country,'
NLT 'Then Israel sent messengers to King Sihon of the Amorites, who ruled from Heshbon, asking for permission to cross through his land to get to their destination.
KJV And Israel sent messengers unto Sihon king of the Amorites, the king of Heshbon; and Israel said unto him, Let us pass, we pray thee, through thy land into my place.

What does Judges 11:19 mean?

Jephthah is explaining that the king of Ammon is wrong in claiming Gilead belonged to his people before being stolen by the Israelites. For one thing, Israel went to great pains to avoid even stepping foot in lands belonging to other peoples (Numbers 20:14–21) on their way across the Jordan River into the land of Canaan (Judges 11:12–18). When they did arrive in territory of Gilead, the Ammonites were not yet there. They were farther east. Further, the Israelites did not even want to stay in Gilead. They just wanted to cross over the Jordan and move on. To do so, though, they would have to travel through the region that became known and Gilead, and it was occupied by the Amorites—not the Ammonites.

Since the Israelites were still not interested in war on the east side of the Jordan, they sent messengers to the king of the Amorites and king of Heshbon. They requested to travel through those territories to get to their own land. The overall point of Jephthah's history lesson to the king of Ammon is that Ammonites were not involved in any of this.
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