Montgomery made an early impression with the Iowa coaches, seeing action his freshman year with the Hawkeyes.  He followed that up as a 3 year starter on the defensive line for the Hawkeyes, making his presence felt each season there.  His playing career never took off to the NFL, although he did make it into camp with the New Orleans Saints.  He spent three seasons in the Arena Football League, finding playing time with the Chicago Rush, the Colorado Crush and his home state Las Vegas Gladiators.  In the midst of his time in the AFL, Montgomery got into coaching, starting at the high school level in Iowa City.  In 2005, Montgomery went to North Iowa Area Community College (NIACC) to take on the responsibility of coaching the defensive line as well as handling Defensive Coordinator duties.  The following season, Montgomery left for a graduate assistant position with the University of Northern Iowa Panthers where he coached the defensive line.  He headed up the D-line at UNI for three seasons, before leaving in 2009 for a position as an Assistant Coach in charge of the defensive line with the Wyoming Cowboys where he just finished his 2nd season. He signed on to join the Indiana Hoosiers as Defensive Tackles Coach for new Head Coach Kevin Wilson, but left for a position as Defensive Line coach with the Michigan Wolverines before the season even started.