Granted, most of this could be 20/20 hindsight but one could reasonably think at least 2. When he was hired he had a team, built by someone else, that was high on hustle and had the best goaltender in the world. It was just a bit short on scoring. Going forward, add a few pieces (a sniper or two) and dont screw anything up (avoid contract squabbles, particularly with your captain) and theres a great shot at cup #1.
By the time most of that cast moved on after 01, a reasonable timespan of turnover, you are still left with an additional 12 years. Which would suggest the ability to build another successful cast within another 6 to 8 years. And for the most part, like it or not, he did. A team high on talent and scoring, good goaltending. All that was missing was some D depth and later, a little more jam. Going forward, he could add a few pieces and not screw anything up and you have a great shot at cup #2.
And here we are.... Rinse, repeat.