Through qualitative analysis, the paper examines the soured relationship between Gambian chiefs and their colonial masters against the backdrop of the legal implications of the disciplinary actions the latter meted out to the former. The article commenced with the theme, before addressing the legal concept of due process, which ensures fairness in the dispensation of justice. By disregarding normal standard legal procedures, the provisions of Magna Carter, and legal precedence, the colonial administrators inflicted draconian punishments on chiefs who dared think outside the box. From archival materials, colonial correspondences, and learned journal publications, the paper advanced explanations for the highhandedness of the colonialists, which degenerated into residency restrictions imposed on the chiefs. The absence of separation of administrative powers, caused by an acute shortage of European personnel, resulted in a situation whereby colonial rule in The Gambia amounted to a situation through which rule of man took precedence over the rule of law. The compelling approach resulting from the lack of collaboration among the chiefs and the colonial administrators fomented discord. The case laws cited in the paper indicate that colonialism in The Gambia remained a case of the strong exerting control over the weak, who had no option but to put up with the inevitable consequences of colonial rule. From different learned sources, instances of banishments in history and how the ancient practice was applied to The Gambia received attention with the aim of elucidating how the colonial administrators adopted legal standards which compromised fair play. With primary materials derived from The Gambia National Archive, instances of chiefs who were at loggerheads with the European colonialists was addressed hence, the objective of the paper is to ascertain the causes and nature of the soured relationship. The findings revealed why the local administrators grappled with situations that were at variance with the normal state of affairs in England. This partly account for the seemingly unorthodox tactics adopted while looking into a number of issues. Consequently, the activities of overseas colonial administrators were glossed over by the colonial office and British parliament as Gambians were perceived to be a people in need of civilization. Therefore, replicating the conditions in England in a frontier territory as The Gambıa will be tantamount to an exercise in futility, as they felt that they should be on higher rungs of the civilization ladder before they could comprehend European conditions. Why the situations obtaining in England are not applied hook line and sinker in the frontier territory was demonstrated. The chequered relationships from the perspectives of both parties was analysed leading to the concluding remarks emphasizing the overbearing approach of the colonialists caused by the lack of cooperation resulted in a bone of contention. This caused the standard of justice to depended on the equality of power to compel; and the strong did what they had the power to do while the weak accepted what was inevitable.