Destriero traded a lot of butterflies, which I think are equivalent to shorting the volatility, since high volatility will take price out of the box which will end up with a loss. please correct me if I am wrong.
Yes,ATM and close to ATM flys typically decrease with a pop in vol.However,deep OTM/Deep ITM flys typically increase with a pop for the very reason you mentioned.. From the little I have read,Des trades vert type structures,flys (split strike,condors as well), some diagnols... He doesn't appear to be a big ratio writer or seller of naked premium.. I think he's has a directional bias as well..
I'll list all of Desty's proven trades below. They're either backed by a sanitized account statement or third-party. No, there aren't any. He's another internet poser. There's evidence that he's ever been profitable.