Did anyone else watch the Jeopardy "Greatest of All Time" tournament? Ken Jennings won largely because, on multiple occasions, he bet everything on Daily Doubles and in Final Jeopardy, even when he was already in first place. If Jennings had missed those questions, I'm sure there would have been a lot of second guessing of his strategy. But my assumption (and I haven't heard him speak to this) is that he recognized that, facing such stiff competition, he was going to have to take some aggressive, calculated risks to vault himself ahead. I would also imagine that he only did it in cases where the category was a subject in which he felt particularly confident.
I bring this up because it reminded me of the argument we often hear that going for it on 4th down, or attempting the two-point conversion, is a bad idea because "If you don't get it, you're screwed." I've mentioned this before in this thread, but loss aversion is a powerful psychological motivator, and we're hard-wired to prioritize avoiding the worst-case scenario. But sometimes you need to recognize that not taking advantage of a situation that calls for aggressiveness, particularly one where the odds of success are in your favor, is itself highly risky. If Jennings had gotten those questions wrong he might have been screwed. But if he hadn't been willing to risk it all he might not have won.
ETA: The big bets were what stood out to me watching the tournament, but I would be remiss if I didn't point out that Jennings ultimately clinched the title by
betting $0 in Final Jeopardy (which was absolutely the right move in that situation). And also that the aggressive betting strategy was pioneered by James Holzhauer (though kudos to Jennings for learning from it and beating him at his own game).