Quote from Martinghoul:
If my recollection is correct, this is precisely the phenomenon that gave us Taleb the Philosopher. Prior to this, he used to be Taleb the Options Trader.
No, Taleb's idea was to own deep OTM premium all the time (and short ATM premium against it to pay for the bleed), then market it as a long-tails hedge to investors. That is quite different to owning deep OTM premium in one direction when a bubble has entered a massively overvalued phase, as one trading strategy amongst several.
Example: Taleb invests in US Treasuries and spends the income on OTM premium each year. Vol collapses from 2003 to 2007 and his returns suck compared to most hedge funds playing the credit bubble. Taleb becomes a philosopher.
Meanwhile, fund X and trader Y follow their normal strategies and make 15-30% per annum (or whatever) from regular trading in 2003-2006, whilst bleeding 1% a year on their housing blowup bets. Once the housing market clearly turns down in 2007, the position pays off big. This assumes no timing ability at all for the housing bears. In reality, once housing turns down in 2006, they have plenty of time to add to positions to score even bigger in 2007-2008.