Cartoons, be it political or comic stripes, have been famed for addressing issues using multi-resources, given the spatial limitations. Cartoonists thus bear the crucial responsibility of effectively conveying their intended messages within the affordances of these constraints. Serving as a form of social commentary, cartoons skillfully tackle weighty societal issues in a subtle yet incisive manner, leaving no ambiguity regarding their targets and messages. This study delves into the pragmatic strategies employed by cartoonists to conceptualize and craft their cartoons, aiming to achieve their communicative objectives. For data, 20 cartoons focused on President Buhari and his handling of various political and economic matters were purposefully selected and analyzed. Drawing upon Odebunmi‘s Contextual Beliefs Theory and Kecskes's dynamic model of meaning, the analysis highlights the reliance of cartoonists on shared beliefs as a pragmatic resource in their creative process. The study also explores how the background knowledge of both cartoonists and readers, alongside societal conventions and shared assumptions, converge to ensure the communicative efficacy of this medium. The findings underscore the influence of socio-political and economic realities on the shared knowledge depicted in the cartoons. Moreover, the deliberate selection of certain lexical items is noted for its reliance on the communal common ground shared by both the subjects and viewers of the cartoons. In conclusion, contextual beliefs play a pivotal role in elucidating the communicative intentions of cartoonists and unpacking the nuanced meanings within cartoons, given their dynamic nature.