Alan Alexander Milne’s authorship was never limited to being the author of the very beloved teddy-bear, far from it. In addition to being a successful playwrite and editing Punch, Milne also wrote several poetry collections which all have been out of print since the 1940s in the entire English-speaking world. His war poetry and social engagement reached far beyond the Bloomsbury group of influential authors and thinkers in the early 20th Century. Milne was a liberal, in terms of what the term denoted in the early 20th century, notably, that is, not in the way we perceive the term today, in the 21st Century. As a perhaps eery echo of the occurrences from a Century ago Milne’s political poetry will be set in motion again; his poetry reflects times of distress and global political unrest. And, in Milne’s own phrasing, 'it’s a silly thing to say', Milne’s poetry pinpoints the ever-present core issues of the inner and external struggles of humanity and individuals. Milne believed in Freedom and liberalism as he knew it in his days, but he also saw what happened when these values were under threat of being sacrificed and lost. Despite all darkness and despair in the early 20th Century, Milne’s focus as a poet was to bring joy and laughter to people, and he chose to do so with poetry, in popular verse, -a bold move in a world where not even courageous people always had someone to voice their situation and their daily struggles. Milne’s poetry is in many aspects the story of the every-day hero, and the ordinary person, yet his depictions of the human struggles is unique and heartfelt. The main focus of this essay is the ways in which Milne’s idea of liberalism effect his poems in portraying serious political topics through the medium of popular verse with its direct relationship to defining and exploring multitude within every word. For the multi-talented Milne his idea of liberalism revolves around Four Freedoms; freedom from want, freedom from fear, freedom of religion, and freedom of expression. Without further delay it is time to bring back into the sphere of well-known (war-)poets from the early 20th Century, the liberal humourist and pacifist war-poet Milne.