I am currently working on assignment from my derivatives class about the portfolio insurance and 1987 market crash. I was asked to perform delta-hedging during 1987 of short puts on S&P 500 index and calculate daily gain/loss on total portfolio (put and hedge). Thus, I used short index futures and risk-free rate. On 19th of October I see a huge loss on put portfolio, which couldn't be offset by gain on short futures. However, I was also asked to do the delta-gamma hedging using 1 month ATM call options on S&P 500. Thus, I gamma neutralize my put portfolio using atm call and then make my portfolio delta-neutral using short futures again. gamma-neutralizing is performed once a month and delta-hedging every day. I again calculate daily/gain loss on my total portfolio. It is even worse (not by a lot though), due to loss on long call portfolio on the crash day! Is it possible that delta-gamma hedge performs worse than delta-hedge???? I would appreciate any advice or comment...