This study examines how Leopold Bloom's behaviour relates to such human matters as fate, free will, chance and courage. Unravelling some of Ulysses' most challenging passages, it reveals the heroism of the novel's main character while also demonstrating the utility of chaos theory for literary analysis. In a detailed assessments of Bloom's thoughts, behaviour and character, the author examines the philosophy of life apparent in Bloom's persistence amidst the day's - and the novel's - dramatic shifts. He demonstrates specific ways in which the stream-of-consciousness technique conveys personality, how Bloom's contingent relationship with his world reveals his fears and hopes, and how he finally pursues his desires despite the sad life that fate seems to have prepared for him. More than this, the author provides one of the most thorough applications of chaos theory to literature yet rendered. He demonstrates how chaos theory expands our understanding of literature and how cross-disciplinary exchange between science and the arts can inform our judgement of the ontological value of both. In the process, he also shows how and why chaos theory offers the best model yet for understanding daily human life and a fresh, humanistic understanding of Joyce.