ABSTRACT This paper involves the psychoanalytic and iconological analysis of two paintings by the Romantic artist Carl Alexander Simon held at the Schlossmuseum in Weimar: Selbstbildnis mit Tirolerhut and Die Braut des Künstlers. Simon produced these paintings in 1830, almost 20 years before travelling to South America, where he continued his artistic career and carried out an ambitious colonisation scheme. This is the first study to scrutinise these paintings. This essay’s primary purpose is to unveil overlooked aspects of Simon’s works, determining the extent to which intricate personality traits began to emerge in these works. The central argument is that various features of these paintings are early instantiations of a messiah complex which will be determinant to understanding his colonising endeavour in Chile.