Born in Oshawa and raised in Whitby, Jason began playing football at the age of nine after watching his older brother Matthew play at the Oshawa Civic Recreation Complex.
Jason played his early years of football with the Oshawa Hawkeyes city football club, receiving numerous team MVP awards. In 2002, he was selected to represent Ontario in the prestigious Canada Cup tournament, held that year in the nation's capital. Team Ontario defeated Team Manitoba in the championship game and Jason was awarded Most Valuable Defensive Player of the tournament.
When he was in Grade 11, Jason began to receive recruitment letters from several American Division I and II schools, as well as Canadian universities from coast to coast. Jason opted to attend McMaster University in Hamilton, Ontario, to play linebacker for the provincially-ranked number one McMaster Marauders. In both 2004 and 2005, Jason was named a Canadian Interuniversity Sport (CIS) First Team All-Canadian – an honour given to the best Canadian football players in the CIS – and awarded the President's Trophy as the defensive MVP of the Ontario University Athletics (OUA) league.
Following his stellar university football career, Jason was drafted in the first round (2nd overall) by the BC Lions Football Club in the Canadian Football League (CFL) where he helped his team win the 2006 Grey Cup Championship in his first year. In 2009, Jason was traded to the Toronto Argonauts Football Club, and in the 2012 season, he won his second championship in the 100th Grey Cup, which was contested on Toronto's home field. After his eighth year in the CFL, Jason was selected in the December 2013 expansion draft by the revived CFL franchise in Ottawa, the REDBLACKS Football Club. Following his 2014 season with the REDBLACKS, Jason retired from football, playing his last game against Toronto in front of his family, friends, and fans.
Jason spent his entire CFL career juggling his education with football, as well as running a real estate investment and property management business. Having earned a double major in Economics and Geography from McMaster, Jason graduated with an MBA from York University's Schulich School of Business in 2014, specializing in international business.