Essays On The Performance Of Option Trading Strategies

This dissertation consists of two parts. In the first chapter, we examine the relative performance of four options-based investment strategies versus a buy-and-hold strategy in the underlying stock. Specifically, using ten stocks widely held in 401(k) plans, we examine monthly returns from strategies that include a long stock position as one component. These strategies are long stock, covered call, protective put, collar, and covered combination. Ignoring early exercise for simplicity, we find that the covered combination and covered call strategies generally outperform the long stock strategy, which in turn generally outperforms the collar and protective put strategies regardless of the performance measure considered. Clearly, from the first chapter, strategies that involve writing options, in general, outperform the ones buying options. The second chapter provides a detailed study of the conditions where option writers can maximize returns while minimizing risk. The nonlinear nature of time value decay in options suggests that, theoretically, holding short positions only when the speed of time decay is high might improve the performance of option writing strategies. We examine monthly returns from five option strategies without a position in the underlying asset. These strategies are: short straddle, short strangle, short guts, “crash-neutral” short straddle, and long iron butterfly. The results from two portfolios are compared: a “benchmark” portfolio using standard SPX options that expire the following month and a weekly portfolio using SPXW options that expire at the end of the weekly holding period. The short strangle strategy with weekly options consistently outperforms the other strategies with both standard and weekly options, even after accounting for transaction costs. This finding suggests that short-dated out-of-the-money options can be useful in improving the risk-return characteristics of an option writing strategy. In an effort to improve the performance of the short straddle strategy, this chapter introduces an extremely short holding period portfolio, by stitching together three weekly option expirations into one week. Although the straddle still underperforms relative to the short strangle, the performance of the short straddle is improved by entering the market 15 minutes before the close and by using the extremely short holding period portfolios.