The Kelly criterion determines optimal bet sizes that maximize long-term growth. While growth is definitely an important consideration, the focus on growth alone can lead to significant drawdowns, leading to psychological discomfort for a risk-taker. Path-dependent risk measures, such as drawdown risk, provide a means to assess the risk of significant portfolio retracements. In this paper, we provide a flexible framework for assessing path dependent risk for a trading or investment operation. Given a certain set of profitable trading characteristics, a risk-taker who maximizes expected growth can still be faced with significant drawdowns to the point where a strategy becomes unsustainable. We demonstrate, through a series of experiments, the importance of path dependent risks in the case of outcomes subject to various return distributions. Based on Monte Carlo simulation, we analyze the medium-term behavior of different cumulative return paths and study the impact of different return outcome distributions. We show that in the case of heavier tailed outcomes, extra care is needed, and optimal might not be so optimal in the end.