Cliff Fletcher is the longest tenured, most decorated, and probably the most fondly remembered GM in Calgary (and Atlanta, I guess) Flames history. Under his reign, he brought the Stanley Cup, two Conference Championships, two Presidents’ Trophies, and three division titles.
He’s mostly known as “Trader Cliff,” due to his pull-the-trigger style that brought big players to strengthen Calgary for the playoffs. He wasn’t afraid to made any trade (including the only cross-sports trade in 1974, to my knowledge), but his drafting resume, both the good and the bad, is often forgotten. Through the draft, he built up a team capable of beating the Canadiens on Forum ice but also tore it down to a decade of forgetfulness.