But on the other hand, if the market is saying there are some risks, and on average it will underprice risk, perhaps its now when the tail risks are present and should be bet on. That's the tough thing about OTM put buying and other forms of tail betting. A lot of the huge profits come in periods where options are overpriced (or they 'look' overpriced)http://www.zerohedge.com/news/2017-...g-3rd-highest-chance-black-swan-crash-history
Right now seems to be a expensive time to do this short of tail hedging
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So perhaps one would apply a "contrarian" approach to OTM put buying? Buy when they don't want them, sell/or dont buy when they want them? It could be an idea
In the 87 crash situation, it would be VERY easy to consider taking profits before Black Monday. Markets were down -14% in a short period of time.
They were oversold (and options were probably expensive) but the real money was made AFTER they were expensive.
Taleb says in a video that in the US stock market 80% or so of the kurtosis is explained by the largest outlier (or something to that effect). If you miss out an big event because you took profits too soon (as the options looked 'expensive'), you might have to wait 30 years to get lucky again
Its hard very this approach, you got to wait so long and need so much luck to see any green