He was the 10th attorney general of West Virginia, as well as at various times on the Wheeling city council and for two years as his home town's solicitor.

Neither his father (who was elected to a part-time position representing Wheeling in the Virginia Senate beginning in 1857) nor his lawyer cousin Aquilla B. Caldwell owned slaves by 1860, and both supported the newly formed Republican party and President Abraham Lincoln elected that year.

Meanwhile, young Alfred was studying at West Liberty Academy, and when his father was appointed consul to the Kingdom of Hawaii, he went with his family.

In early 1867, his father returned to Wheeling, having been removed from office by President Andrew Johnson because of irregularities in the accounts and accusations that his son-in-law had been enriching himself.

[1] Alfred Jr. studied law under his father's guidance and was admitted to the West Virginia bar in 1868, the year of his father's death and when his uncle, Aquilla Bolton Caldwell (who had been elected as the new state's first attorney general), was appointed West Virginia's 5th attorney general.