Born on May 12, 1849, in Eaton Rapids, Michigan, Montgomery read law in 1870.

He served in the United States Army Seventh Michigan Cavalry in 1864, during the American Civil War.

He was an Assistant United States Attorney for the Western District of Michigan from 1877 to 1881.

[1] Montgomery was nominated by President William Howard Taft on March 9, 1910, to the United States Court of Customs Appeals (later the United States Court of Customs and Patent Appeals), to the new Presiding Judge seat authorized by 36 Stat.

He was confirmed by the United States Senate on March 30, 1910, and received his commission the same day.