Humour is often used for aesthetic, pedagogical and sociocultural purposes in satire, either dividing and/or uniting interlocutors, and simultaneously uncovering power relations, i.e., injustice and inequality (Sousa 2009a-c; Sousa, Bazenga, & Antunes 2009). Further studies are claimed (Duch 2014) to be still undertaken about the way humour is conveyed in (trans)cultural / translingual contexts as the ones in insular settings like the archipelago of Madeira (Portugal). Hence, it is relevant to see whether humour strategies evidenced in a satirical newspaper; Re-nhau-nhau (a local publication issued in Madeira throughout the 20th century), could entail a way of raising citizens’ consciousness of the sort of power relations in cosmopolitan contexts (following the notions by Norrick, & Chiaro 2009, Dovchin, & Canagarajah 2019). Locals / residents in Madeira have been reported to be both under the sovereign influence of Portugal (as a Portuguese region), and the British socio-cultural, economic, as well as linguistic influence, due to the century-long (trans)cultural contact (Sousa 2017). Thus, this paper of empirical and exploratory kind intends to account for the way power relations are addressed in humour discursive practices, selected from a satirical newspaper issued in Madeira during dictatorship in Portugal. Do caricaturists only portray unfair situations via diverse humorous strategies to make readers aware of injustice to be overturn, in part, via the implementation of fairer government measures in the following decade? A pragmalinguistic approach underpins the analysis of twenty-two caricatures, selected from Re-nhau-nhau (between 1934 and 1948), in the line of research suggested by Kecskes, & Romero-Trillo (2013). A set of British public figures, like Henry Hinton and Graham Blandy, frequently displayed in this satirical paper, have led the selection criterion of the corpus to be studied, given their meaning potential as multimodal discursive practices. This study entails the study of coherence, irony (i.e., echoic irony in Attardo’s stance, 2000), speech acts (Austin 1962; Searle 1996) and face-threatening acts (Brown, & Levinson 1987) as mechanisms to achieve humour and social intervention goals in the corpus selected for this study. Research findings point to the relevance of pragmalinguistic strategies to disambiguate humour strategies as well as the underlying aesthetic and pedagogical effect of caricatures in Re-nhau-nhau. Power and agency are overturned and defamiliarized in the dialogic process of meaning making always with a humorous undertone, sometimes making use of conceptual metaphors and translanguaging. Considering the principle of ridendo castigat mores, this satirical paper points to some discrepancy concerning the way the sets of British residents (Mr Hinton and Mr Blandy) are represented, being Henry Hinton the most openly criticized figure at the time.