The Olympic Gold is a funny example because the job is not really the same as building an NHL franchise. It doesn't have am amateur draft, contract negotiations, salary caps, trades or many of the things that make up a big part of the NHL GMs job. It's a bit more like picking an all star team while having a lot of other qualified NHL leadershio on your staff.
I am not bashing Yzerman.
I often use him as an example when talking about Marner or Matthews and their inability to win the big games. Yzerman was in Detroit for 14 years before they won a cup. His scoring rates dropped more than the average player's did from regular season to playoffs. Eventually they surrounded Yzerman with so much talent they became a winner; talent like Fedorov, Larionov, Shanahan, Kozlov, Draper, Lidstrom, Fetisov, Murphy and Vernon. There was no salary cap back then.
Maybe that example makes the case for patience? Maybe it points out that Yzerman was not the winner he is remembered as.
Is Shanahan a winner? He has won cups and Olympics Gold as a player. Does that "winner pedigree" cross from player to GM? I think he is a winner.