This research investigates the linguistic implications of transgenderism with the objective of determining the impact of transgenderism on existing gender theories. The orientation of this research is situated in the linguistic field of pragmatics and adopts Yule’s (1996) classification of presupposition as the theoretical framework for this study. The research problem is hinged on the fact that disruptive processes create upheavals for existing structures such that the affected structures require critical rescue. In this connection, transgenderism and its attendant complications pose strong challenges for gender pragmatics. The data is a real-life video, captioned “Sorry, I’m A Man”, collected from JERRY SPRINGER – Transsexual Tell All official channel on YouTube. The method of this research is qualitative. The methodological paradigm is interpretive, based on content analysis. The relevance of this research is based on its contribution to resources geared towards salvaging humanity from adulteration and destruction, particularly being that language and gender are essential constituents of the existence of human beings.