The younger Montgomery was a pupil of George Poindexter and Edward Turner, and established a law practice in partnership with Samuel S. Boyd, a native of Maine; their firm "was for many years one of the leading ones of the State".
[1] Following the resignation of Judge Joshua Child from the state supreme court, Montgomery was one of several candidates put forth for the seat.
[3] Upon his election by the legislature to the circuit and supreme court of the state in November, 1831, defeating William L. Sharkey for that position "by a considerable majority",[3] Montgomery became the first native Mississippian on the bench.
[4] Montgomery appeared as a witness in an 1840 controversy, where he was described as "a distinguished and influential Whig, who adheres to the maxim that 'the private station is the post of honor'".
[5] In 1845, he was appointed to a committee of five jurists asked to prepare resolutions commemorating the death of U.S. Supreme Court justice Joseph Story.