[Arkham]

As quozl alluded to, in Army of Darkness Ash is tasked with remembering a specific phrase to send the demons back in the end, yet he messes it up. He messes it up because he thinks he's got it handled and is overconfident/arrogant about it. That's a perfect representation of the character. Yet, he does manage to keep fighting and generally is successful overall.

That's what we'd need to capture, however we go about doing it.

The gamble mechanic allows for a bit of overconfidence or swinging for the fences by the player, rather than playing it safe. Play it safe for moderate bonus, or go big and potentially win big. Not sure if what I laid out completely captures the idea as-is.