The last to do it was Jim Devellano in 1997, and he'd been with the Red Wings since 1982.
So it seems a Cup "winning pedigree" for a GM candidate is completely irrelevant in the modern game.
First, Ken Holland was AGM of the Wings in 97 then won 3 more Cups as GM.
Second, there are only 22 total Cup winning GMs since expansion in 67. There is no one single formula for hiring a GM that is guaranteed to win a Cup. And since NONE of us on this board are in the rooms, listening to the decisions being made with each team, determining who is influencing what moves.. all we can do is look at resumes from afar.
The reason I like hiring a GM from a winner is looking at the teams on the rise right now, their GMs largely came from the recent winners. Cliff Fletcher in Minnesota came from the Pens under Shero when they won. Murray with the Ducks was SVP Hockey Ops under Burke when they won. Bergevin with the Habs was Dir PP then AGM with the Hawks when they won.
I concede, there is no single magic formula for this decision. But when I look at our choices, we can find a guy who has won before and ask him to repeat that process, to use that same blueprint, to do what his boss did before. Or we can find a guy who hasn't won before and ask him to do something he hasn't done before, to perform better than his previous boss performed.
One of my criteria for a promotion is, excellence in your previous position, which is pretty easy to spot. If you think you can determine someone's "vision" and talent from the vantage of message board poster, reading a few articles on the web, well more power to ya.