[1][2] Montgomery grew up on the family farm and was educated at local public schools before leaving to attend Hanover College, where he was part of the Sigma Chi fraternity.
[1][2][3][4] Back in Seymour, Montgomery opened up a private law practice and became involved in local politics as a Republican.
He was also active in numerous local fraternal organizations, namely the Knights of Pythias and the Masonic Order, and was also a member of the private Columbia Club in Indianapolis.
[1][2][5][6] In 1904, Montgomery was elected to the Indiana Supreme Court to succeed Justice Alexander Dowling.
One of them, Theophilus Harlan Montgomery, was a Princeton University graduate and practiced law with his father in Seymour.