He spent his childhood and teenage years helping out in the store owned by his parents, Eli and Mary Darby Henderson.
[2] As tensions built between the North and the South, Henderson was chosen as one of three delegates to represent Pike County at Alabama's state secession convention.
A few months later, the American Civil War began after Confederate troops attacked Fort Sumter in South Carolina.
Henderson was a captain in the 57th Alabama Infantry Unit, Company B;[3] he remained in the Confederate Army throughout the duration of the war.
In 1869, Henderson moved his mercantile business to the nearby city of Troy, Alabama to be closer to the Mobile and Girard Railroad.