In this article, we explore how presidential risk orientations affect force employment decisions through an analysis of the use of unmanned weaponry during the Bush and Obama administrations. We hypothesize that the conception of risk plays an integral part in this choice of weaponry. In order to examine our hypothesis, we utilize the verbs-in-context system of operational code analysis to quantify the risk propensities of President Bush and President Obama during the Afghanistan War from 2001 to 2013. At the aggregate level, we find that the two presidents exhibit unique interpretations of risk with respect to manned versus unmanned weaponry. We further disaggregate our data to examine whether these preferences are fixed or fluctuate with situational changes. We find that President Bush’s risk calculations are influenced by a number of situational variables, highlighting the importance of changing decision contexts in explaining risk behaviors. President Obama’s risk calculations, on the other hand, remain constant over time lending credence to the importance of overall risk propensity in determining risk-taking behaviors. Our findings indicate that risk is an important variable in explaining the means of force employed during conflict, and that the source of this behavior can vary by leader.