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Joshua 17:1 tells us that Machir was the first to settle the lands of Bashan, and Gilead. I would presume it was Machir and his clan who took the land from the Amorite king Og of Bashan.
Machir had a son named Gilead (whome the land was later named), and he had a daughter who married Hezron the Judahite. Machir's grandson, the son of Hezron, was named Segub. And Segub's son, (Machir's great grandson), was named Ja'ir. Ja'ir was the judge of Bashan (during the period of judges, c. 1150 bc), and he governed 60 settlements; approx. 23 in Gilead and 37 in Bashan, these towns were later taken over by the Geshurites and Arameans around 900 to 850 BC.