J.R. Poindexter was born on October 23, 1860 to Oscar and Malinda Jane Haviland Poindexter. He was the grandson of James Poindexter, founder of Poindexter Station, and Robert S. Haviland, founder of Havilandsville, of Harrison County, Kentucky. After schooling at Smith's Classical School, J.R. taught for a year and then began surveying roads and performing some contract work. James Robert Poindexter was one of Harrison County's most influential builders and contractors. In the 1880s, he completed many road and bridge projects. Over the next several decades, he shaped the growth of Cynthiana and other communities through landmark construction projects, water and sewer systems, public buildings, churches, and early paved streets.
Pictured is J.R. Poindexter circa 1880.