I asked Chabot about 9-11 trading:
“Yes, it is known that large quantities of put options (a bet on a stock’s price to fall) were purchased for American Airlines and United Airlines stock in the days leading up to the September 11 attacks, resulting in profits for the undisclosed investors, although federal investigators found no evidence that this trading was done by the terrorists themselves”
The WTC had been recently purchased and heavily insured as well.