This study aims at identifying the features of sentence structure in the paradoxes poetry in the light of transformational generative theory, which was authored by the American linguist Noam Chomsky. The driving motive for this study is what I have noticed in the common factor of defamation poetry of both poets: Jarir and AL Farazdag in terms of deep infrastructure of sentences when exchanging defamation poems as each one tries to possess the basic meaning when it comes to honor and transfer the meaning to the other when it comes to dishonor. This domain of poetry race is found to be more suitable for applying the generative transformational grammar in terms of converting the sentence from deep infrastructure to surface structure by the action of transformational grammar rules as explained by Chomsky in most of his works and applied by so many researchers to Arabic structures. This research has shown that the poetic race between the two poets; Jarir and AL : Farazdaq was a transformational one because when analyzing works of both poets, we can discover that both of them employed the environment in building critical structure to challenge the other one. These facts were the meanings being derived from dominant customs and traditions and the common history and genealogies, which are converted by poets to a language to his audiences and then the poets make improvements in formulating linguistic structures. Such disposition can be considered as one of the tools of the generative grammar and its rules. The results of this study can be summed up in the fact that both poets have used transformational method so much in their poems that no stanza of their poem is found free from such method. It is noticed that the employed transformations are limited to four rules as follows: 1. Transformation rule with addition 2. Transformation rule with replacement 3. Transformation rule with order 4. transformation rule with omission. It is noticed that the rule of transformation with addition was dominant in the poetry of each poet, while the rule of transformation with omission was less dominant and the sentence features in both poets' poetry are found to be more similar because both belonged to the same literature era. Therefore, to apply such work to two poets that belong to different eras can be more beneficial and distinctive in identifying features of grammatical structures. In view of this work, we can approach studies and research that aim at transformation in the poetry of paradoxes and others in order to determine the transformation relation with the author from one part and his relation with purposes of the discourse form another part and notice rules of transformation quantitively and qualitatively and thus, we can come up with findings that are beneficial to both criticism and linguistic fields.