Fleury played quarterback for Frederick High School in Frederick, Maryland, before transferring to Seneca Valley High School in Germantown, Maryland, where he played under his stepfather head coach.
[1] He only started as a senior and was selected All-Metro after throwing for 2,025 yards and 26 touchdowns while leading the team to an undefeated record and the state championship.
[2][3] He received no NCAA Division I athletic scholarship offers and thus joined the Maryland Terrapins as a walk-on in 1998.
[5] He returned to Towson in 2009 and served four years as special teams coordinator and defensive backs coach.
[6] Fleury entered the National Football League (NFL) in 2013 and served as quality control coach for the Buffalo Bills.