Ian Fleming’s debut novel Casino Royale (2015) introduces the iconic character James Bond. The savvy British spy who must save the world from Soviet villain is a cultural icon the world over. Yet not much is known of his personal political leanings. Fleming once claimed that James Bond’s politics lies just left of center. In this essay I analyze where James Bond lies on the left-right political scale by using Cichoka & Dhont’s (2018) “Big-five personality model”.Research has been made about the contextual, historical and political settings of the Bond novels such as Jeremy Black’s (2001) “The politics of James Bond: from Fleming's novels to the big screen” which serves as a complement to this research. Black’s (2001)claims suggest that Britain struggled for dominance after The Second World War as they were financially in ruin and although Britain lost some of its colonies, they still had many territories under their control. However, with the rising power of the Soviet Union, the nationalistic feeling in Britain grew as their reputation as a powerful empire needed to be upheld. Therefore, a need for a strong British symbol grew, which also acted as a reason for why Fleming created James Bond.The essay concludes that James Bond represents a specific part of Great Britain. The analysis has shown James Bond is a product of his time by symbolizing the longing for the return of the great British empire. This is supported by the fact of him scoring low on categories such as Agreeableness and Openness combined with the fact that he harbors anti-Communist beliefs. The analysis show that he acts in a manner that would highlight the colonial days of Britain where their strength had not yet diminished as opposed to the times after the Second World War. As such, the actions of James Bond, together with his explicit views suggest that he lies slightly more towards the right on the political scale and thus, disputesthe claim of Ian Fleming.