He played college football at North Carolina Central University in Durham, North Carolina. Massey served as the interim head football coach at Livingstone College in Salisbury, North Carolina from 2005 to 2006 and as the head football coach Shaw University in Raleigh, North Carolina from 2012 to 2015. He was fired from his position at Shaw on December 10, 2015.
Massey's football career involved stints as a collegiate athlete at North Carolina Central University in Durham, North Carolina. He held coaching positions at Livingstone College in Salisbury, North Carolina (2005-2006) and Shaw University in Raleigh, North Carolina (2012-2015), before being terminated on December 10, 2015.