In the USA alone, around 22 million patients annually discuss the need for surgical procedure with their surgeon. On a global scale, more than 200 million patients are exposed to the risk of undergoing a surgical procedure every year. A crucial part of the informed consent process for surgery is the understanding of risk, the probability of complications, and the predicted occurrence of adverse events. Ironically, risk quantification, risk stratification, and risk management are not necessarily part of a surgeon’s core skillset, considering the lengthy surgical training curriculum towards technical excellence. The present review was designed to provide a concise historic perspective on the evolution of our current understanding of risk and probability, which represent the key underlying pillars of the shared decision-making process between surgeons and patients when discussing surgical treatment options.