Ultimately, he was doomed to fail. His job was to advocate the right technologies at the right time. Yet MS rarely makes the right choices in this area. Technology decisions are made by political GMs who want to hold on to their empires. They are made by VPs who don't want to sacrifice short term profits for a longer term vision.
Steve Jobs made an excellent point at the D conference this year about how Apple tries to pick technologies that are in their "Spring". These are technologies that are on their way up. Certainly Steve has the luxury of not worrying as much about backwards compatibility, etc. But he certainly has the courage of his convictions to pick a path that's best for his company and customers.
I don't think Ray had that kind of fortitude, and unfortunately, I don't think he had that kind of power. Ultimately, the CEO needs to push the technological vision of Microsoft. Leaving it to mid-level managers will only result in further mediocrity.