Another good phrase: "picking up pennies in front of a steamroller" - which is when you do the opposite strategy (lots of little gains, but with the risk of losing it all and more).
I love this term. One of my friends at work manages trading systems (for use by actual financial experts) and we were discussing this discredited strategy recently. It's killed one or two big companies, despite being a Nobel prize winning idea.
This specifically refers to a call of strategies that are the equivalent of writing a put option. The short term cash flows from the premium are not commensurate with the tail risk. Both LTCM and CDS on subprime are examples of this type of strategy going up. Typically the options have a duration of years which raises the probability of a tail event significantly.