As Najam Haider has recently illustrated, premodern Muslim historians occasionally altered minor details or embellished speech in the hope of making larger points to intended audiences. In an attempt to transcend debates over veracity in late medieval Arabic historiography, this paper presents a fifteenth-century case study of how the historical narratives of the Syro-Egyptian litterateur Ahmad ibn 'Arabshah (d. 1450) sought to bring textual order to complex realities of political uncertainty. The creation of monologues and dialogues presented both in his biography of Tamerlane ('Aja'ib al-maqdur) and his panegyric for sultan al-Zahir Jaqmaq (Ta'lif al-tahir) reveal many of the author’s historical truth claims and the processes and literary tools through which he made his historiographical texts meaningful. In examining Ibn 'Arabshah’s usage of Genette’s categories of mimetic, transposed, and narrated speech, this paper studies the author’s literary strategies to decode unique political messages on justice and kingship embedded in his historical writing. Ibn 'Arabshah constructed vastly different textual personas of his two biographical subjects. The first was the Central Asian commander amir Temur (r. 1370-1405) – presented consistently throughout the biography as an unjust tyrant. The second subject, sultan Jaqmaq of Cairo (r. 1438-1453) – was alternately set forth by the author as an ideal Muslim sovereign. Both texts include numerous examples of how Temur and Jaqmaq spoke to subordinates, emissaries, and common people, and how they vocalized their thoughts on justice, righteous war and royal succession. In both cases, the dialogue Ibn 'Arabshah separately attributed to his chief antagonist and protagonist links directly to messages he sought to convey to elite audiences, and how the author made sense of contemporary moments of uncertainty at times of succession between the political orders established in Cairo by the sultans Barsbay (1422-1438) and Jaqmaq. A close textual and chronological relationship exists between Ibn 'Arabshah’s two texts, and many of the good qualities of Jaqmaq are in direct dialogue with the bad qualities of Temur. Ibn 'Arabshah’s lengthy monologues served his historical actors as a venue through which to share their innermost thoughts - along the lines of a Shakespearean soliloquy - laying their consciences bare and delivering motivations to the audience. These extended speeches prove to be a worthy subject of analysis which reveal the ways in which they served the author as literary tools to move the overall direction of the historical narratives in which they appear.