Born in Morristown, New Jersey, and raised in Shrewsbury, Montgomery played football at Red Bank Regional High School, where he had hoped to be a linebacker rather than a punter.
[3] As a junior, he was honored by the Football Writers Association of America (FWAA) as a first-team All-American,[4] and as a senior he was selected to the second-team by United Press International.
[6] Montgomery was selected in the third round of the 1988 NFL draft by the Houston Oilers.
[7] From 1988 to 1997 he spent time with the Houston Oilers, Detroit Lions, and Baltimore Ravens.
[9] Montgomery died on August 23, 2020, in Grand Rapids, Michigan, after succumbing to a long-term illness.