Abstract. Maximum drawdown, the largest cumulative loss from peak to trough, is one of the most widely used indicators of risk in the fund management industry, but one of the least developed in the context of measures of risk. We formalize drawdown risk as Conditional Expected Drawdown (CED), which is the tail mean of maximum drawdown distributions. We show that CED is a degree one positive homogenous risk measure, so that it can be linearly attributed to factors; and convex, so that it can be used in quantitative optimization. We empirically explore the differences in risk attributions based on CED, Expected Shortfall (ES) and volatility. An important feature of CED is its sensitivity to serial correlation. In an empirical study that fits AR(1) models to US Equity and US Bonds, we find substantially higher correlation between the autoregressive parameter and CED than with ES or with volatility. We are grateful to Robert Anderson for insightful comments on the material discussed in this article; to Alexei Chekhlov, Stan Uryasev, and Michael Zabarankin for their feedback on a previous draft of this work; to Vladislav Dubikovsky, Michael Hayes, and Márk Horváth for their contributions to an earlier version of this article; to Carlo Acerbi for providing detailed comments on a previous draft; and to the referees and editors of Mathematics and Financial Economics for their valuable feedback.