I think it’s exceedingly rare to win a Grey Cup as a player, and then become the Head Coach of that same team and win another Grey Cup.
I can only think of a handful of examples:
- Kent Austin, SSK (1989, 2007)
- Pinball Clemons, TOR (1996 etc, 2004)
- Dave Dickenson, CAL (1998 as a backup, 2018 )
- And, I think, Ralph Sazio (1953, 1960s)
Hopefully we can add to this list very soon.
Have I missed any?