This research paper will investigate linguistic strategies of avoiding the prosecution’s powerful questions during the Harold Shipman hearing. It will focus on closely reading two sample courtroom transcripts of direct examination and cross-examination question pairs by screening and identifying categories of resistance as proposed by Newbury and Johnson in 2006. The findings of this comparative analysis between direct examination and cross-examination support that strategies of resistance are primarily invested in cross-examination rather than during direct examination by Shipman’s own counsel. On a deeper level of analysis, this research will investigate occurrences of a linguistic evolution from the four categories of resistance clustered from weak resistance to strong resistance from “Avoidance” to “Correction” to “Contest” to “Refusal” and will show that a progression is a sign of an ever so more agitated state of mind of the plaintiff trying to resist the powerful questions. As the cross-examination transcript indeed shows progressive strategies of resistance, this research will also match the results with a second more dynamic model of linguistic representation based on Olsson and Luchjenbroers in 2022. The latter model informs us of the existence of linguistic strategies of aiming at moving targets motivated by unequal power relations between questioner and respondent before a court of law. The results of this study will shift from the mere act of pigeonholing difficult interrogative responses by means of a linguistic taxonomy model to an investigation of the dramatic shifts in question and answer pairs (interrogatives, declaratives and non-questions or statements) ultimately aiming to dismantle Shipman’s composure during cross-examination. As there is to date no linguistic analysis of the Shipman trial in the relatively new field of Forensic Linguistics, this model may invite for further research in interrogative strategies in courtroom studies.