As a freshman in 2011, he had 82 tackles, nine sacks, 21 tackles for loss, 3 forced fumbles and 2 fumble recoveries, while helping the team reach the NJCAA title game. Gregory enrolled at Arizona Western College. In addition to numerous scholarship offers in football, Gregory also drew some interest from Division I basketball teams. Following his senior season, he was ranked as one of the top 15 players in the state of Indiana. In football, he posted 92 tackles and 17 sacks.
He attended Hamilton Southeastern High School in Fishers, Indiana, where he was a two-sport athlete in football and basketball. His father, Ken Gregory, played college football at Northwestern.
Gregory was born in Jacksonville, Florida and moved seven different times.
