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Note: douglas irby winn was born at mason county, kentucky; this was likely the area that would become fleming county. it is at fleming county he married elizabeth tribby rawlings on 1 jan 1810. they lived at pretty prairie, near urbana, champaign, oh., until returning to fleming co. around 1820. of the several places winn lived in his lifetime, it is at fleming that he made his mark. as teacher and schoolmaster at hillsboro, he set about making genteel citizens of the county's youth. he rapidly developed a reputation as the finest educator in the county, especially in mathematics, over an approximate 20-year career. it is said in fleming's histories that winn was saddled with ever greater responsibilities and given teaching positions involving more 'challenging' students, while his physical abilities flagged; it is under these conditions that winn retired and removed to round prairie, callaway, mo. around 1840, just after both douglas and elizabeth's fathers had died in 1838/9.
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