This paper is a critical analysis of The Chattering Wagtails of Mikuyu Prison, a collection of poems by Jack Mapanje. It aims at demonstrating how new voices in politics are often compelled to silence. It explores the factors that make the hope of the masses dissipate to make room for a great despair in the heart of both the masses and the political opponents and activists who in our case here are writers. To conduct this work, we have based our analysis on new historicism and post-colonial criticism using the qualitative research method. The results of our findings reveal that some people get involved in politics either directly or indirectly with the hope of bringing about changes in the management of their country so as to put it on the path of sustainable development. Unfortunately, the powerholders resort to all the possible means to show resistance through all possible means to silence and discourage them. This state of affairs constitutes a hindrance to a true development and a good political leadership in Africa where powerholders do not tolerate opposition at all.