Phew is this an old post. But I have some different theories. I've been recently doing extensive research on this "insurance policy" because I beleive it will come into play very soon. I beleive this all revolves around the blood vials. The players from MotD all have the ability to travel into the afterlife. An ability Richtofen may want to use as an insurance policy. If they "don't like where they end up" , they have the afterlife to fall back on. Richtofen has The Weasel as the useful blood and the other as a baseline. I originally thought the insurance policy was something along the lines of the insurance policy in the movie Primer (spoilers) . Their insurance policy was to go to the beginning if all else fails. But, as you said, Dempsey didn't see it coming. So it had to be some crazy shit for him to not see it coming. That's why I crossed that theory off. No matter what theory I have written down, 95% of them revolve around those damn blood vials.