Are we talking about greatest Red Wing within the context of a player who played for the Wings, or the greatest Red Wing within the context of what he meant to/did for the team and the city during his tenure?
Within the context of option A, the order should be:
1. Sawchuk. Unarguably one of the top four goalies in NHL history. (Roy, Plante and Hall are the others in my top four). Won four Cups, four Vezinas and was a seven-time all-star. Held most goaltending records when he died in 1970.
2. Lindsay. Very tough call between Terrible Ted and Red Kelly. But Lindsay is the second-best left winger ever, he is one of the all-time great combinations of skill, grit and tenacity, and his leadership abilities rank among the best ever.
3. Kelly. Won eight Stanley Cups. A key part of four-time Cup winning teams in Detroit and Toronto. Starred at both defence and centre. One of the most versatile players ever. Won the first-ever Norris Trophy.
4. Yzerman. Finished his career as one of the top-five scorers in NHL history. An outstanding combination of skill, class and leadership. Recognized that the most important hockey was in the playoffs. Captain of three Cup champions.
In terms of what they meant to the Red Wings, I'd give the nod to Yzerman. Longest-serving captain in NHL history with one organization just about says it all. He also captained the team to three Cups (the first one ended a 42-year drought), and was the epitomy of everything that was right about the game for much of his career.