The Italian colonial enterprise, including its legal efforts, was notably transient and disorganized, especially when compared to its European counterparts. As a result, Italian legal professionals working in the colonies were compelled to develop their own—often original and creative—legal approaches in managing the complex relationships between legal authorities and colonial subjectivities. This essay analyzes the extraordinary efforts of one such colonial jurist, Arnaldo Bertola. Bertola was a judge in Libya and Rhodes, a Professor of colonial law at the University of Turin 1930’s, and a legal expert in Mogadishu, Somalia, after the war. Bertola’s case is noteworthy because of his innovative thinking, his remarkable personality, his unusual cultural eclecticism, and his steady inner faith in the value of religious freedom. The essay explores his writings not only for his legal achievements, but also for his very human uncertainties in confronting the stranger, the colonized, and the foreigner: in a word, the other.