Riley was an offensive and defensive lineman at Creston High School in Grand Rapids, Michigan. Grand Rapids Creston High School is the only Grand Rapids Public School to ever go to the state finals in football (1999). Riley was a sophomore during that season.
Riley played college football at the University of Michigan from 2003 to 2006 after redshirting in 2002. In 2004, he started the majority of the year as a left guard. In 2005–2006 he started at right tackle due to many injuries at the position forcing coaches to move Riley. Riley's body type was projecting him as an early round draft pick at guard but the Wolverines needed him to shore up the edge as a tackle his last two years at Michigan.
Riley signed with the Carolina Panthers after being passed over in the 2007 NFL draft. He was cut on September 1, 2007, but was signed to the team's practice squad. He was re-signed during the 2008 off-season, but was waived on July 23.
Riley was re-signed by the Panthers on August 7, 2008, after the team waived offensive tackleCharles Spencer, the same player the Panthers acquired when they waived Riley two weeks earlier. He was waived during final preseason cuts on August 30.
Riley was signed to the New York Giants' on December 31, 2009. On January 5, 2010, Riley was signed to a reserved/future contract. He was waived on August 7.
Hartford Colonials
Riley was signed by the Hartford Colonials of the United Football League on September 16, 2010. He reported to the team and was the starting left tackle in the season opener with the Colonials. Four games into the season Riley dislocated his knee.
