The Toronto Argonauts have won the most Grey Cup championships (16), followed by the Edmonton Eskimos (14) and Winnipeg Blue Bombers (10). The Winnipeg Blue Bombers have made the most Grey Cup appearances (24).
Winnipeg (21)
Edmonton Eskimos with 13
Toronto Argonauts have won 16 Grey Cups, the last of which was in 2012. However, only 6 of these were won after the creation of the CFL in 1958.
3 players are tied for this record. Jack Wedley, Bill Stevenson and Hank Ilesic have each won 7 grey cups.
The salaries of CFL coaches are not public knowledge. However, players and coaches in the CFL make considerably less than the NFL. It is estimated that a coach makes 500,000 per year.
Toronto Argonauts-16 Grey Cups 1914, 1921, 1933, 1937, 1938, 1945, 1946, 1947, 1950, 1952, 1983, 1991, 1996, 1997, 2004, 2012.
Winnipeg Blue Bombers with 10 (last in 1990) after Toronto Argonauts' 16 and Edmonton Eskimos' 13.
Hank Ilesic and Bill Stevenson are tied with seven CFL Grey Cup victories. Jack Wedley also was on the Grey Cup winning team seven times, but that was in the days before the CFL. My father was on six Grey Cup winners and one losing side. Again, that was before the CFL. Seven different players are tied for most Grey Cup appearances, with nine.
All of the present teams in the Canadian Football League (CFL) have their names engraved on the Grey Cup. Two former CFL teams were also Grey Cup winners: Ottawa Rough Riders and Baltimore Stallions. Several other non-CFL teams have won the Grey Cup, but none since 1944.
Toronto Argonauts have 16 Grey Cup wins from their first in the 6th Grey Cup in 1914 to their win in the 100th Grey Cup in 2012. The team that has won the most grey cups in a row would be the Edmonton Eskimos who won 5 in a row between 1978-1982.
Toronto Argos with 16.
Toronto has won a total of 23 grey cups but that isn't the answer to the question. First, the question asked which team, not which city. Second, the question specified winning Grey Cups in the Canadian Football League. The CFL was not formed until 1958, so Grey Cup victories prior to 1958 don't count. The correct answer is the Edmonton Eskimos, with ten Grey Cup victories (and eight losses, which also qualifies the Eskies for most appearances). Grey Cup victories for Toronto teams include 4 by U of T, 2 by Balmy Beach, 1 by Toronto RCAF, and 16 by Argonauts.