ABSTRACT Italian colonial authorities heavily relied on the askaris (i.e. native soldiers) throughout the history of colonialism to alleviate the economic and political burdens of colonial warfare. For that, the askaris became privileged intermediaries for the Italians and emerged as a de facto elite within colonial society, seeking social mobility for themselves and their families. After the end of the Second World War, the askaris lost their role as soldiers, but gained new relevance as political intermediaries for Italian or British plans regarding the final resolution of the Italian colonies affaire. The article delves into the life stories of two askaris, which were documented by the author on 3rd November 2009, in Tripoli. Their memories highlight the relationships of friendship or intimacy that existed with the colonisers and showcase the askaris’ ability to downplay colonial elements of domination and oppression through their intermediation. Being an askar entailed, on one hand, questioning the political and racial boundaries of society, and on the other hand, challenging the agendas of nationalist groups. The transition to independence indeed involved a struggle between colonisers and the colonised, as well as among various groups of colonial subjects, all vying for power within the post-colonial State and society.