He wasn’t in the province very long and his record wasn’t legendary, but owning a 1989 Grey Cup ring makes John Gregory a Roughrider Legend!

          The now 73-year-old had not been a C-F-L head coach he was hired by the Riders, a farnchise that had no playoff appearances in the previous 11 years. In his first season as Saskatchewan's head coach, Gregory led the Green and White to an 11–7 record and a playoff berth. He won the Annis Stukus Trophy as the league's coach of the year. The following year the Roughriders finished 9–9 and won the 77th Grey Cup, their first since 1966. After a 1–6 start in 1991, he was fired and replaced by Don Matthews. He had a 35–43–1 overall record in Saskatchewan.

          Gregory went on to coach Hamilton for a couple of seasons and has bounced around Arena Football ever since. In fact, this year Gregory is the offensive coordinator for the Tampa Bay Storm. It is his first position where he has not been a team head coach for more than two decades.

          But, his magical 1988 and 89 Saskatchewan teams are enough to earn John Gregory status as a Roughrider Legend!