Montgomery attended Dodge City High School, where he played as a quarterback, before being switched to running back as senior.
[1] He accepted a football scholarship from Kansas State University, where he played as a running back and wide receiver.
On August 1, 1972, he was traded along with wide receiver Billy Parks to the Dallas Cowboys in exchange for running back Duane Thomas, who was a player the Chargers coveted.
He replaced Otto Stowe in the starting lineup after he suffered a broken ankle in the seventh game of the season against the Philadelphia Eagles,[4] but Montgomery would also fell to injury in the next game and open the door for third-string rookie Drew Pearson to take over and never relinquish the position.
On July 5, 1974, he was traded to the Houston Oilers, after he signed a contract for the 1975 season with the Birmingham Americans of the World Football League.