After the war, which had financially ruined his family, Montgomery briefly worked as a travelling entertainer. Montgomery was admitted to the bar in 1867, and became county attorney for Warrenton until the office was abolished the following year. He also working as an editor for the
Warrenton Courier, and starting his own newspaper,
The Living Present. He practiced in
Memphis, Tennessee, from 1873 to 1876, then returned from to Warrenton to practice from 1876 to 1893, when he moved to
Raleigh, North Carolina, where he remained in practice until his election to a vacated seat on the Supreme Court in 1894. In 1896, he was elected for the full term of eight years, serving until January 1905, and authoring a number of well-regarded opinions. He then returned to private practice, also serving by appointment as a standing master for the
United States Circuit Court for the Eastern District of North Carolina. ==Personal==