This article discusses a certain state of the political imagination of a Canada-in-the-making and outlines the matrix of common representations of the Confederation in the years 1864 – 1867 in western and eastern Canada. My research is based on a corpus of cartoons and editorials that are by and large about risk and calculated risk, with the sub-themes being the unity or disintegration of geographical, national and even personal identities. Between monstrous depictions and family scenes, the texts and images of this Canada-in-the-making are very rich in capturing the country’s general mood. The visual imagery includes hydras, octopuses and Gorgon heads as manifestations of the fears and concerns about the Confederation. In terms of the narratives, vivid descriptions of the threat of innocent or savage girls being married are frequently deployed by the newspapers to promote the idea of the Confederation, as embodied in the city of Ottawa as the seat of government. This article aims to open a broad sociocritical analysis on a number of aspects of the representations of a Canada-in-the-making, such as the envisioned role of its parliament, democratic representation, the ministerial stability of elected officials, and the building of an identification with the Confederation.