Born in Charles City County, Virginia,[1] Waddill was educated by private tutors and attended Norwood Academy.

[1] Waddill then resumed his private legal practice as well as successfully ran for the Virginia House of Delegates (a part time position) and was re-elected, serving from 1885 until 1889.

[1] The United States Senate confirmed the nomination on March 22, 1898, and Judge Waddill received his commission the same day.

[1] One of his famous cases involved suffragettes sentenced to jail for protesting as "the Silent Sentinels" outside the White House.

[1] Waddill was nominated by President Warren G. Harding on May 26, 1921, to a seat on the United States Court of Appeals for the Fourth Circuit vacated by Judge Jeter Connelly Pritchard.