Drawing from the black swan theory developed by Nassim Nicholas Taleb, which defines a black swan to be an unexpected high-impact event which people tend to think is easily explained in hindsight, this study explores risk evaluation in relation to conspiratorial beliefs. The hypothesis states that a higher degree of conspiratorial thinking correlates with a proclivity to evaluate risks as being either very high or very low. The method used was a web-based survey consisting of 16 different events, both conspiratorial and non-conspiratorial, of which a total of 291 American participants got to assess the risk by paying a hypothetical sum of money for insuring themselves against the consequences of each event. This was followed by a second survey to assess the participants’ degree of conspiratorial thinking. The first analysis measured the correlation between conspiratorial thinking and the standard deviation of the participants’ money distribution, corresponding to degree of disparity in risk assessment. Based on two clusters that were observed in the aggregate of scores on the conspiracy scale, the participants were divided into conspiracy theorists and non-conspiracy theorists. The second analysis measured main- and interaction effects of what types of events the participants insured themselves against, and what types of events that participants prioritized depending on their degree of conspiratorial thinking. The hypothesis that a higher degree of conspiratorial thinking correlates with a tendency to evaluate risks as being either very high or very low was not supported. The results show that a higher degree of conspiratorial thinking correlates with a lower standard deviation in money distribution, and that the conspiracy theorists insured themselves against the consequences of less likely and more conspiratorial events compared to the non-conspiracy theorists. This study supports the idea that conspiracy theorists tend to follow a consistent conspiratorial narrative, believing in several conspiracy theories and not just one.