Players like Phil and Mike who often take insurance think they always run worse than everyone else. They do sometimes get sick hands where they are a huge favorite and the opponent just happens to hit the hand they need to take the pot
In this hand, Helmuth has floped trips w/ top kicker against opponents KK and has the opponent committed all in. They run the hand 4 times and despite Helmuth being 85% to 15% favorite, only won 1 out of 4 times. See it here: