Montgomery was born in Greenwood, South Carolina. He attended Greenwood High School, and played for the Greenwood Eagles high school football team.
Montgomery also ran track and field in addition to football. He was a member of the high school relay team. He ran a personal best time of 11.34 seconds in the 100 meters at the 2009 Regional 1 Class AAAA. He also competed in the shot put, he finished 4th with a throw of 14.20 meters.
Considered a four-star recruit by 247Sports.com, Montgomery was listed as the No. 3 weak-side defensive end in the nation in 2009.

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