His father, Richard Perrin Caldwell, died when he was an infant, and he had great difficulty in obtaining an education.

As a youth, he attended public school and worked on the family farm in the summer and fall.

[1] In 1863, he became a private soldier in a North Carolina company of the Confederate Army and served until the end of the war.

[1][2] From 1881 to 1895, he was a member of the Virginia House of Delegates from Hanover County, serving as Speaker from 1887 onward.

Cardwell died at his home, Prospect Hill, on March 19, 1931, and was interred at Woodlawn Cemetery in Ashland, Virginia.