Throughout history, chocolate has been used to treat a wide variety of ailments, and in recent years, multiple studies have found that chocolate can have positive health effects, providing evidence to a centuries-long established use; this acknowledgement, however, did not have a straight course, having been involved in religious, medical and cultural controversies. Christian Europe, in fact, feared the exhilarating effects of new drinks, such as chocolate, coffee and tea. Therefore, these beverages would have been banished, had not doctors and scientists explained that they were good for the body. The scientific debate, which reached its peak in Florence in the 18th century, regarded the therapeutic effectiveness of the various chocolate components: it was necessary to know their properties first, in order to prepare the best cacao concoction for every patient. When Dietetics separated from Medicine, however, chocolate acquired the role of vehicle for easing the administration of bitter medicines, being associated to different health problems. The recent rediscovery of the beneficial use of cacao and chocolate focuses upon its value as supplemental nutrition. Building a bridge to the past may be helpful to detect the areas where the potential health benefits of chocolate are likely to be further explored.