Craighead played college football at the University of Texas at El Paso and attended Mother Teresa High School in Nepean, Ontario.
Craighead played lacrosse for the Mother Teresa High School Titans.
He also played city league football for the Nepean Redskins for ten years.
[1] Craighead spent the 2008 season playing football for the Fork Union Military Academy Blue Devils.
He was made his CFL debut, starting against the Montreal Alouettes, on June 28, 2014.