In this paper we adopt Charles Sanders Peirce's concept of iconicity to analyse pictural communication. While visual semiotics has a well-developed structural school, the concepts of visual semiotics stemming from Peirce's pragmatic sign theory are often overlooked. The specific purpose of this study is to explore the semiotics of visual signs, exemplified by two prominent pictures of former US President Donald Trump. We argue that Peirce's semiotic framework for iconicity in visual signs (the image, the diagram, and the metaphor) offers a useful framework for discussing how the meaning of visual signs is motivated. On this basis, we propose that Peirce's concept of hypoicons provides us with a richer understanding of how visual signs acquire meaning and how their interpretation varies across cultural habits, and collateral experience.