Fleming as a St. Rita Alum recorded 105 tackles including 15 tackles for loss and nine sacks, and helped lead St. Rita to the Class 7A state championship. As a senior, he led St. Rita to the Chicago Prep Bowl city championship and was chosen to play in the U.S. Army All-American Bowl in San Antonio, Texas. He went on to commit to Notre Dame, playing defensive end and outside linebacker during his tenure for the Irish. His impressive stats earned him a spot in the draft where he was taken on by the 49ers. He eventually sign with the New England Patriots in 2014. Fleming went on to play in Super Bowl XLIX championship, and recovered a Josh Cribbs muffed punt in the AFC Championship Game.