As a senior, he led his high school to the Chicago Prep Bowl city championship.

For his efforts, he was chosen to play in the U.S. Army All-American Bowl in San Antonio, Texas.

Over his four-year career, he accumulated 157 tackles, including 32 for loss, fourteen and a half sacks, two interceptions, and nine pass deflections.

[8] Fleming played primarily on special teams during the Patriots' playoff run and Super Bowl XLIX championship, and recovered a Josh Cribbs muffed punt in the AFC Championship Game.

On September 5, 2015, he was released from the Patriots during the team's 53-man roster cuts, and was re-signed to New England's practice squad two days later.

[9] On January 14, 2016, Fleming rescued a woman from a three-car accident in which a big rig made an immediate turn and caused cars to pile up behind it.