Complex sentence: He served as special consultant to the Alouette's head coach, Marc Trestman, during the 2009 and 2010 CFL season's both Grey Cup winning seasons for the team, and was a Grey Cup ring in the spring of 2010.
Split into simpler sentences: He served as special consultant to the Alouettes' head coach, Marc Trestman during the 2009 and 2010 CFL seasons, which were both Grey Cup winning seasons for the team. He was given a Grey Cup ring in the spring of 2010.