Montgomery was born in Ionia, Michigan in 1909 and graduated from the University of Michigan in 1929. He worked as a teacher, was first elected to the House in 1944, and was defeated for re-election in 1946. Montgomery unsuccessfully sought election to the House in 1950, 1954, and 1956; as State Superintendent of Public Instruction in 1947; and to the Senate in 1952. He was a delegate to the 1948 Democratic National Convention.