I think too many owners/team presidents are either limited and/or afraid to take chances in their vision for their teams. How else can you explain how often average/poor GMs and coaches get 2nd or 3rd jobs?
I also think this leads these owners/presidents to confuse experience with success. Because how someone could hire Jarmo Kekäläinen over Mathieu Darche right now is beyond the beyond.
I think the answer to that is pretty simple. How many 'young tigers' actually pan out at their first go-round with a Cup? I didn't go back to research this yet, but in the last 30 years, how many first-time GM's have a Cup versus those who are on their 2nd/3rd GM job?
Let's not forget that Dubas was THE boy-wonder and now he's on his 2nd job.
Big money owners are probably more comfortable with someone who has the experience more than we are here. Failure is sometimes the best teacher for long-term success.
Ranger fans are ready to launch Drury into an active volcano as a first-timer.
As I'm searching online, it's hard to find a site that even lists Cups by GM.
Also, should point out that for Kekalainen, how do you factor having to build in Columbus vs getting a shot in Boston or Montreal?
I think an owner is looking for a vision that they are comfortable with more than a track record, since so many factors not in the team's control can derail a Cup run. Whether a fresh face, or a retread, it's still about designing a strategy and part of that is having the owner comfortable with what the strategy is. These are still businesses, that just happen to be aligned with a sport, instead of a chain of stores or a software product, etc., and the owner needs to be sold on that too, not just how you draft or trade and that is also where experience can trump the 'hot thing'.