Who was the Highest paid CFL player in history?

Carl Robinson of Toronto FC in Major League Soccer (Both US and Canadian teams) makes $330K (US) a year.

Link: http://sports.espn.go.com/espn/wire?section=soccer&id=3329838

Other professional teams in Canada (Vancouver, Montreal) play in the USL-1 which includes teams from the USA, Canada, and Puerto Rico. It is doubtful any player outside of MLS makes more than a 5 digit salary playing professional soccer in Canada.