Coffee leaf rust (CLR) is caused by the biotrophic pathogenic fungus Hemileia vastatrix. Despite being the most researched coffee disease, mysteries still exist relating to its epidemiology and biology. The objective of this work is to highlight past and present events concerning this prominent coffee disease. We start with an historical overview of the homeland of Coffea arabica, the Afromontane forest of south-west Ethiopia, and then follow its journey across the globe linked to colonial trade and power struggles. We report the relevance of CLR to coffee production today, with a focus on the Americas and summarize unproven hypotheses in relation to the cause of recent epidemics. We present an original hypothesis concerning the first major outbreak occurring in 1869 in Ceylon (Sri Lanka), based on geopolitical connections to global trade. We review old and new options for management of the disease. The likelihood of a yet undetected alternate host of H. vastatrix is also considered as an additional piece of the epidemiological puzzle. Finally, we reflect on the interactions between H. vastatrix and a changing climate. By better understanding past events, linked to CLR, we may be better prepared for future outbreaks.