The translation is a multi-layered text production practice that is governed by various determinants. The rich textures of translated texts are evaluated under the title of “translation criticism” based on varying criteria. Practical conceptual designs and concerns over objectivity constitute the primary elements of translation criticism that are conducted on case studies. This study elaborates on the translation Dr. Jekyll ve Mr. Hyde (2009) by Öznur Ayman and the original text Strange Case of Dr. Jekyll and Mr. Hyde (1885) by Robert Louis Stevenson. Emerging as one of the most retranslated works in Turkish literature, this work has several versions in the Turkish repertoire. This study aims at providing a detailed comparative analysis of the target and the source text on the basis of the postulate designed by Katherina Reiss (2000). With a preliminary focus on the text typology in the literary category, the evaluation is conducted through the language category which includes semantic, lexical, grammatical, and stylistic elements; and the pragmatic category which consists of the immediate situation, subject matter, time, place, audience, speaker factors respectively. It should be noted that the design incorporates the black box of the translation process, the translator, into the scheme of translation criticism. The ideal behind the efforts in this paper is to (re)test the potentials and limitations of translation criticism on a case study and contribute to the existing literature on one of the rather ignored fields of translation studies, “translation criticism”.